Form F-10 FAIRFAX FINANCIAL HOLDIN

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September 17, 2021 11:22 AM EDT

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As filed with the Securities and Exchange Commission on September 17, 2021

Registration No. 333-

UNITED STATES
SECURITIES AND EXCHANGE COMMISSION
WASHINGTON, D.C. 20549

FORM F-10

REGISTRATION STATEMENT
UNDER
THE SECURITIES ACT OF 1933

Fairfax Financial Holdings Limited
(Exact Name of Registrant as Specified in its Charter)

Canada

(Province or Other Jurisdiction of Incorporation or Organization)

6331

(Primary Standard Industrial Classification Code Number)

Not Applicable

(I.R.S. Employee Identification No.)

Suite 800, 95 Wellington Street West
Toronto, Ontario M5J 2N7
Telephone: (416) 367-4941

(Address, including postal code, and telephone number, including area code, of Registrant’s principal executive offices)

CT Corporation System
111 Eighth Avenue, 13th Floor
New York, NY 10011 U.S.A.
Telephone: (212) 894-8700

(Name, Address (Including Zip Code) and Telephone Number (Including Area Code) of Agent for Service in the United States)

				Copies to:
	Derek Bulas Fairfax Financial Holdings Limited Suite 800, 95 Wellington St. W. Toronto, Ontario M5J 2N7 (416) 367-4941			Mile T. Kurta, Esq. Christopher R. Bornhorst, Esq. Torys LLP 1114 Avenue of the Americas New York, New York 10036 (212) 880-6000			David Chaikof Robbie Leibel Torys LLP 79 Wellington St. W. Toronto, Ontario M5K 1N2 (416) 865-0040

Approximate date of commencement of proposed sale of the securities to the public:
as soon as practicable after this registration statement becomes effective.

Province of Ontario, Canada

(Principal Jurisdiction Regulating this Form F-10 Offering)

It is proposed that this filing shall become effective (check appropriate box):

A. ☐

upon filing with the Commission, pursuant to Rule 467(a) (if in connection with an offering being made contemporaneously in the United States and Canada).

B. ☒

at some future date (check appropriate box below):

1. ☐

Pursuant to Rule 467(b) on ( ) at ( ) (designate a time not sooner than seven calendar days after filing).

2. ☐

Pursuant to Rule 467(b) on ( ) at ( ) (designate a time seven calendar days or sooner after filing) because the securities regulatory authority in the review jurisdiction has issued a receipt or notification of clearance on ( ).

3. ☐

Pursuant to Rule 467(b) as soon as practicable after notification of the Commission by the registrant or the Canadian securities regulatory authority of the review jurisdiction that a receipt or notification of clearance has been issued with respect hereto.

4. ☒

After the filing of the next amendment to this form (if preliminary material is being filed).

If any of the securities being registered on this Form F-10 are to be offered on a delayed or continuous basis pursuant to the home jurisdiction’s shelf prospectus offering procedures, check the following box. ☐

CALCULATION OF REGISTRATION FEE

Title of Each Class of
Securities to be Registered

Amount to be
Registered

Proposed
Maximum
Offering Price
Per Unit(1)

Proposed
Maximum
Aggregate
Offering Price(1)

Amount of
Registration
Fee(1)

3.375% Senior Notes due 2031 of Fairfax Financial Holdings Limited

US$600,000,000

N/A

US$600,000,000

US$65,460

(1)

The notes being registered are offered (i) in exchange for 3.375% Senior Notes due 2031 previously sold in a transaction exempt from registration under the Securities Act of 1933, as amended, and (ii) upon certain resales of the notes by broker-dealers. The registration fee has been computed based on the face value of the notes solely for the purpose of calculating the amount of the registration fee, pursuant to Rule 457 under the Securities Act of 1933, as amended.

The Registrant hereby amends this registration statement on such date or dates as may be necessary to delay its effective date until the registration statement shall become effective as provided in Rule 467 under the Securities Act of 1933, as amended or on such date as the Commission, acting pursuant to Section 8(a) of the Securities Act of 1933, as amended, may determine.

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PART I

INFORMATION REQUIRED TO BE DELIVERED TO OFFEREES OR PURCHASERS

A copy of this preliminary short form prospectus has been filed with the U.S. Securities and Exchange Commission pursuant to a U.S. registration statement, which has not yet become effective. Information contained in this preliminary short form prospectus may not be complete and may have to be amended. The securities may not be sold until the registration statement becomes effective with the U.S. Securities and Exchange Commission.

No securities regulatory authority has expressed an opinion about these securities and it is an offence to claim otherwise.

Information has been incorporated by reference in this prospectus from documents filed with securities commissions or similar authorities in Canada and filed with, or furnished to, the U.S. Securities and Exchange Commission. Copies of the documents incorporated herein by reference may be obtained on request without charge from the office of our Corporate Secretary at Suite 800, 95 Wellington Street West, Toronto, Ontario, Canada, M5J 2N7 (telephone: (416) 367-4941), and are also available electronically at www.sedar.com and at www.sec.gov.

PRELIMINARY SHORT FORM PROSPECTUS

New IssueSeptember 17, 2021

Fairfax Financial Holdings Limited

Exchange Offer for $600,000,000 of its
3.375% Senior Notes due 2031

The Company

•

Fairfax Financial Holdings Limited (the “Company”) is a holding company which, through its subsidiaries, is engaged in property and casualty insurance and reinsurance and the associated investment management. The Company and its subsidiaries (“Fairfax”, “we”, “our”, “us”) operate through a decentralized operating structure, with autonomous management teams applying a focused underwriting strategy to our markets. We seek to differentiate ourselves by combining disciplined underwriting with the investment of our assets on a total return basis, which we believe provides above-average returns over the long-term. We provide a full range of property and casualty products, maintaining a diversified portfolio of risks across classes of business, geographic regions, and types of insureds. We have been under current management since September 1985. Our head and registered office is located at Suite 800, 95 Wellington Street West, Toronto, Ontario, Canada M5J 2N7. Our telephone number is (416) 367-4941.

The Exchange Offer

•

If all the conditions of the exchange offer (the “Exchange Offer”) are satisfied, the Company will exchange up to $600,000,000 aggregate principal amount of its 3.375% Senior Notes due 2031 issued on March 3, 2021 (the “Initial Notes”) that are validly tendered and not validly withdrawn for an equal principal amount of 3.375% Senior Notes due 2031 (the “Exchange Notes”) that have been registered under the United States Securities Act of 1933, as amended (the “Securities Act”).

•

You may withdraw your tender of Initial Notes at any time before the expiration of the Exchange Offer.

•

The Exchange Offer will expire at 5:00 p.m., New York City time, on , 2021, unless the Company extends the Exchange Offer, in which case, the Exchange Offer will expire at 5:00 p.m., New York City time, on the date to which the Exchange Offer is extended (the “Expiration Date”).

The Exchange Notes

•

The terms of the Exchange Notes to be issued in the Exchange Offer are substantially identical to the Initial Notes except that, unlike the Initial Notes, the Exchange Notes will be freely tradable in the United States by persons not

(continued on next page)

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(continued from cover)

affiliated with us, will not bear legends restricting their transfer and will not contain the registration rights and additional interest provisions of the Initial Notes.

•

The Exchange Notes will be issued in United States dollars.

•

The Exchange Notes will be issued in minimum denominations of $2,000 principal amount and integral multiples of $1,000 in excess thereof.

•

There is no market through which the Exchange Notes may be sold and purchasers may not be able to resell the Exchange Notes issued pursuant to the Exchange Offer. This may affect the pricing of the Exchange Notes in the secondary market, the transparency and availability of trading prices, the liquidity of the Exchange Notes, and the extent of regulation affecting the Company. See “Risk Factors” commencing on page 9.

Before participating in the Exchange Offer, please carefully read this short form prospectus, including the section entitled “Risk Factors” commencing on page 9.

For a more detailed description of the Exchange Notes, please refer to the section in this short form prospectus entitled “Description of the Notes” commencing on page 56.

This offering of the Exchange Notes is made by the Company, which is a foreign issuer in the United States and is permitted, under a multijurisdictional disclosure system adopted by the United States and Canada, to prepare this short form prospectus in accordance with Canadian disclosure requirements. Prospective investors should be aware that such requirements are different from those in the United States. The financial statements incorporated herein by reference have been prepared in accordance with International Financial Reporting Standards (“IFRS”) as issued by the International Accounting Standards Board (“IASB”). Thus, such financial statements may not be comparable to financial statements of United States companies.

Prospective investors should be aware that owning the Exchange Notes may subject you to tax consequences both in the United States and in Canada. This short form prospectus may not describe these tax consequences fully and such consequences for investors who are resident in, or citizens of, the United States may not be described fully herein. You should read the tax discussion in this short form prospectus. You should consult your own counsel, accountant or other advisors for legal, tax, business financial and related advice regarding the Exchange Offer.

The enforcement by investors of civil liabilities under U.S. federal or state securities laws or other laws of the United States may be affected adversely by the fact that the Company is formed outside the United States, that most of the Company’s directors and officers, as well as certain of the experts named in this short form prospectus, reside outside of the United States, and that many of the assets of the Company and the assets of such persons are located outside the United States.

THESE SECURITIES HAVE NOT BEEN APPROVED OR DISAPPROVED BY THE UNITED STATES SECURITIES AND EXCHANGE COMMISSION (THE “SEC”) OR ANY CANADIAN SECURITIES REGULATORY AUTHORITY, NOR HAS THE SEC OR ANY CANADIAN SECURITIES REGULATORY AUTHORITY PASSED UPON THE ACCURACY OR ADEQUACY OF THIS SHORT FORM PROSPECTUS. ANY REPRESENTATION TO THE CONTRARY IS A CRIMINAL OFFENCE.

Prospective investors should be aware that, during the period of the Exchange Offer, the Company or its affiliates, directly or indirectly, may bid for or make purchases of the securities to be distributed or to be exchanged, or certain related securities, as permitted by applicable laws or regulations of Canada or its provinces or territories.

No underwriter has been involved in the preparation of this short form prospectus or performed any review of the contents of this short form prospectus.

Each broker-dealer that receives Exchange Notes for its own account pursuant to the Exchange Offer must acknowledge that it will deliver a prospectus meeting the requirements of the Securities Act in connection with any resale or transfer of such Exchange Notes in the United States. The letter of transmittal states that by so acknowledging and by delivering a prospectus, a broker-dealer will not be deemed to admit that it is an “underwriter” within the meaning of the Securities Act. This short form prospectus, as it may be amended or supplemented from time to time, may be used by a broker-dealer in connection with resales or transfers of Exchange Notes in the United States received in exchange for Initial Notes where such Initial Notes were acquired by such broker-dealer as a result of market-making or other trading activities. The Company has agreed that it will make this short form prospectus available to any broker-dealer for use in connection with any such resale or transfer for a period that ends the earlier of (i) 180 days after the date on which the registration statement that includes this short form prospectus is declared effective by the SEC, and (ii) the date on which participating broker-dealers are no longer required to deliver a prospectus in connection with market-making or other trading activities. See “Plan of Distribution”.

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Table of Contents

	Page
ABOUT THIS PROSPECTUS		i
PRESENTATION OF FINANCIAL INFORMATION		ii
DOCUMENTS INCORPORATED BY REFERENCE AND WHERE YOU CAN FIND MORE INFORMATION		iii
ENFORCEABILITY OF CIVIL LIABILITIES AGAINST FOREIGN PERSONS		v
FORWARD-LOOKING INFORMATION		vi
SUMMARY TERMS OF THE EXCHANGE OFFER AND THE EXCHANGE NOTES		1
DESCRIPTION OF THE BUSINESS		5
RISK FACTORS		9
USE OF PROCEEDS		27
CONSOLIDATED CAPITALIZATION		28
EARNINGS COVERAGE RATIOS		29
DESCRIPTION OF MATERIAL INDEBTEDNESS AND OTHER COMMITMENTS		30
THE EXCHANGE OFFER		31
INSURANCE REGULATORY MATTERS		39
DESCRIPTION OF THE NOTES		56
PRIOR SALES		66
CERTAIN ERISA CONSIDERATIONS		67
CERTAIN U.S. FEDERAL INCOME TAX CONSIDERATIONS		69
PLAN OF DISTRIBUTION		70
LEGAL MATTERS		71
INDEPENDENT REGISTERED PUBLIC ACCOUNTING FIRM		72
AGENT FOR SERVICE OF PROCESS		73
DOCUMENTS FILED AS PART OF THE REGISTRATION STATEMENT		74
CERTIFICATE OF THE COMPANY		C-1

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ABOUT THIS PROSPECTUS

You should rely only on the information contained in or incorporated by reference in this short form prospectus. We have not authorized any other person to provide you with different information. If anyone provides you with different or inconsistent information, you should not rely on it. You should not assume that the information provided by this short form prospectus is accurate as of any date other than the date on the front of this short form prospectus. Our business, financial condition, results of operations and prospects may have changed since the date on the front of this short form prospectus. The Exchange Notes are being offered only in jurisdictions in which offers and sales are permitted.

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PRESENTATION OF FINANCIAL INFORMATION

As the majority of our operations are in the United States or conducted in U.S. dollars, we report our consolidated financial statements in U.S. dollars in order to provide more meaningful information to users of our financial statements. In this short form prospectus except where otherwise indicated, all dollar amounts are expressed in U.S. dollars, references to “$”, “US$” and “dollars” are to U.S. dollars and references to “Cdn$” are to Canadian dollars.

We have prepared our audited consolidated financial statements as at and for the years ended December 31, 2020 and 2019 in accordance with IFRS as issued by the IASB. We have prepared our unaudited interim consolidated financial statements as at June 30, 2021 and for the three and six months ended June 30, 2021 and 2020 in accordance with IFRS as issued by the IASB applicable to the preparation of interim financial statements including IAS 34 Interim Financial Reporting.

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DOCUMENTS INCORPORATED BY REFERENCE AND WHERE YOU CAN FIND MORE INFORMATION

The following documents filed by us with the securities commission or similar authority in each of the provinces and territories of Canada are specifically incorporated by reference in this short form prospectus:

(a)

our annual information form for the year ended December 31, 2020, dated March 5, 2021;

(b)

our audited consolidated financial statements and the notes thereto, including consolidated balance sheets as at December 31, 2020 and 2019 and consolidated statements of earnings, comprehensive income, changes in equity and cash flows for each of the two years in the period ended December 31, 2020, and management’s report on internal control over financial reporting, together with the report of the independent registered public accounting firm dated March 5, 2021 on these consolidated financial statements and on the effectiveness of internal control over financial reporting;

(c)

management’s discussion and analysis of financial condition and results of operations for the annual consolidated financial statements as at and for the periods referred to in paragraph (b);

(d)

our management proxy circular dated March 5, 2021 in connection with the annual meeting of shareholders held on April 15, 2021;

(e)

our unaudited interim consolidated financial statements and the notes thereto, including the consolidated balance sheets as at June 30, 2021 and December 31, 2020, the consolidated statements of earnings, comprehensive income and cash flows for the three and six months ended June 30, 2021 and 2020 and the consolidated statements of changes in equity for the six months ended June 30, 2021 and 2020; and

(f)

management’s discussion and analysis of financial condition and results of operations for the unaudited interim consolidated financial statements as at and for the periods referred to in paragraph (e).

Any documents of the types referred to in paragraphs (a) to (f) above (excluding confidential material change reports) filed by us with the securities regulatory authorities in Canada after the date of this short form prospectus and prior to the termination of the Exchange Offer shall be deemed to be incorporated by reference herein.

Any statement contained in a document incorporated or deemed to be incorporated by reference in this short form prospectus shall be deemed to be modified or superseded for the purposes of this short form prospectus to the extent that a statement contained in this short form prospectus, or in any other subsequently filed document which also is or is deemed to be incorporated by reference herein, modifies or supersedes that statement. The modifying or superseding statement need not state that it has modified or superseded a prior statement or include any other information set forth in the document that it modifies or supersedes. The making of a modifying or superseding statement shall not be deemed an admission for any purposes that the modified or superseded statement, when made, constituted a misrepresentation, an untrue statement of a material fact or an omission to state a material fact that is required to be stated or that is necessary to make a statement not misleading in light of the circumstances in which it was made. Any statement so modified or superseded shall not be deemed, except as so modified or superseded, to constitute a part of this short form prospectus.

Information has been incorporated by reference in this short form prospectus from documents filed with securities commissions or similar authorities in Canada and the United States. Copies of the documents incorporated by reference herein and the Indenture (as defined below) may be obtained without charge by writing to the Company at Suite 800, 95 Wellington Street West, Toronto, Ontario, M5J 2N7. Attention: Corporate Secretary. Our telephone number at that address is (416) 367-4941.

The Company has filed a registration statement on Form F-10 with the SEC regarding the Exchange Offer, which includes this short form prospectus as part of such registration statement. For further information about us and the Exchange Offer, you should refer to the registration statement and its exhibits. This short form prospectus summarizes material provisions of agreements and other documents to which we refer you. Copies of these agreements and documents have been included as exhibits to the registration statement and you are encouraged to read these in their entirety.

iii

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The Company is currently subject to the periodic reporting and other informational requirements of the U.S. Securities Exchange Act of 1934, as amended (the “Exchange Act”) and in accordance therewith files reports and other information with the SEC. However, the Company is a “foreign private issuer” as defined in Rule 405 of the Securities Act and therefore is not required to comply with Exchange Act provisions regarding the furnishing and content of proxy statements, and its officers and directors are exempt from the reporting and short swing profit recovery provisions contained in Section 16 of the Exchange Act. Additionally, under a multijurisdictional disclosure system adopted by the United States and Canada, public reporting documents and other information (including financial information) may be prepared in accordance with the disclosure requirements of the provincial and territorial securities regulatory authorities of Canada, which differ from those in the United States.

The SEC maintains an Internet website that contains reports and other information about issuers who file reports with the SEC. The address of that website is www.sec.gov. The Company also files information, such as periodic reports and financial information, with the Canadian Securities Administrators, which may be accessed at www.sedar.com. These filings can also be found on the Company’s website, which may be accessed at www.fairfax.ca.

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ENFORCEABILITY OF CIVIL LIABILITIES AGAINST FOREIGN PERSONS

The Company is a corporation organized under the laws of Canada and some of its assets are located in, and most of its directors and officers are residents of, Canada. As a result, it may be difficult for investors outside of Canada to effect service of process outside of Canada upon the Company’s directors or officers, or to realize outside of Canada upon judgments of non-Canadian courts predicated upon civil liability of such directors or officers under non-Canadian securities laws. See “Agent for Service of Process”.

We have been advised by Torys LLP, counsel to the Company, that a monetary judgment of a U.S. court predicated solely upon civil liability provisions of U.S. federal securities laws would likely be enforceable in Canada if the U.S. court in which judgment was obtained had a basis for jurisdiction that was recognized by a Canadian court for such purposes. We have also been advised by our counsel that it is less certain that an original action could be commenced in Canada on the basis of liability predicated solely upon such laws.

The Company has irrevocably appointed CT Corporation System, 28 Liberty Street, New York, New York 10005, as its authorized agent for service of process in any legal action or proceeding arising out of or relating to the Indenture and the Exchange Notes for actions brought under United States federal or state securities laws or for actions brought by either trustee or for any actions arising out of or related to the Indenture or the Exchange Notes in any New York Court, and has irrevocably submitted to the jurisdiction of the New York Courts for such purposes.

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FORWARD-LOOKING INFORMATION

This short form prospectus contains “forward-looking statements” and “forward-looking information” (collectively, “forward-looking information”) within the meaning of applicable Canadian and United States securities legislation. Any statements made by us or on our behalf may include forward-looking information that reflect our current views with respect to future events and financial performance. The words “believe,” “anticipate,” “project,” “expect,” “plan,” “intend,” “predict,” “estimate,” “will likely result,” “will seek to” or “will continue” and similar expressions identify forward-looking information. This forward-looking information relates to, among other things, our plans and objectives for future operations and underwriting profits. We caution readers not to place undue reliance on this forward-looking information, which speak only as of their dates. We are under no obligation to update or alter such forward-looking information as a result of new information, future events or otherwise, except as may be required by applicable securities laws. This forward-looking information is subject to known and unknown risks, uncertainties and other factors that could cause our actual results, performance or achievements to be materially different from any future results, performance or achievements expressed or implied by such forward-looking information. These uncertainties and other factors, which we describe in more detail elsewhere in this short form prospectus, or in documents incorporated by reference herein, include, but are not limited to:

•

a reduction in net earnings if our loss reserves are insufficient;

•

underwriting losses on the risks we insure that are higher than expected;

•

the occurrence of catastrophic events with a frequency or severity exceeding our estimates;

•

changes in market variables, including interest rates, foreign exchange rates, equity prices and credit spreads, which could negatively affect our investment portfolio;

•

risks associated with a global pandemic caused by a novel strain of coronavirus (“COVID-19”), and the related global reduction in commerce and substantial downturns in stock markets worldwide;

•

the cycles of the insurance market and general economic conditions, which can substantially influence our and our competitors’ premium rates and capacity to write new business;

•

insufficient reserves for asbestos, environmental and other latent claims;

•

exposure to credit risk in the event our reinsurers fail to make payments to us under our reinsurance arrangements;

•

exposure to credit risk in the event our insureds, insurance producers or reinsurance intermediaries fail to remit premiums that are owed to us or failure by our insureds to reimburse us for deductibles that are paid by us on their behalf;

•

our inability to maintain our long term debt ratings, the inability of our subsidiaries to maintain financial or claims paying ability ratings and the impact of a downgrade of such ratings on derivative transactions that we or our subsidiaries have entered into;

•

risks associated with implementing our business strategies;

•

the timing of claims payments being sooner or the receipt of reinsurance recoverables being later than anticipated by us;

•

risks associated with any use we may make of derivative instruments;

•

the failure of any hedging methods we may employ to achieve their desired risk management objective;

•

a decrease in the level of demand for insurance or reinsurance products, or increased competition in the insurance industry;

•

the impact of emerging claim and coverage issues or the failure of any of the loss limitation methods we employ;

•

our inability to access cash of our subsidiaries;

•

our inability to obtain required levels of capital on favorable terms, if at all;

•

the loss of key employees;

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•

our inability to obtain reinsurance coverage in sufficient amounts, at reasonable prices or on terms that adequately protect us;

•

the passage of legislation subjecting our businesses to adverse requirements, additional supervision or regulation, including additional tax regulation, in the United States, Canada or other jurisdictions in which we operate;

•

risks associated with applicable laws and regulations relating to sanctions and corrupt practices in foreign jurisdictions in which we operate;

•

risks associated with government investigations of, and litigation and negative publicity related to, insurance industry practice or any other conduct;

•

risks associated with political and other developments in foreign jurisdictions in which we operate;

•

risks associated with legal or regulatory proceedings or significant litigation;

•

failures or security breaches of our computer and data processing systems;

•

the influence exercisable by our significant shareholder;

•

adverse fluctuations in foreign currency exchange rates;

•

our dependence on independent brokers over whom we exercise little control;

•

impairment of the carrying value of our goodwill, indefinite-lived intangible assets or investments in associates;

•

our failure to realize deferred income tax assets;

•

technological or other change which adversely impacts demand, or the premiums payable, for the insurance coverages we offer;

•

disruptions of our information technology systems;

•

assessments and shared market mechanisms which may adversely affect our insurance subsidiaries; and

•

adverse consequences to our business, our investments and our personnel resulting from or related to the COVID-19 pandemic.

See the “Risk Factors” section of this short form prospectus and the documents incorporated by reference into this short form prospectus for a further discussion of these risks and uncertainties.

Should one or more risk, uncertainty, contingency or other factor materialize or should any factor or assumption prove incorrect, actual results could vary materially from those expressed or implied in the forward-looking information. Accordingly, you should not place undue reliance on forward-looking information. We do not assume any obligation to update or revise any forward-looking information after the date of this short form prospectus or to explain any material difference between subsequent actual events and any forward-looking information, except as required by applicable law.

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SUMMARY TERMS OF THE EXCHANGE OFFER AND THE EXCHANGE NOTES

We are able to incorporate by reference information into this short form prospectus, which means we can disclose important information to you in documents outside this short form prospectus. This summary is qualified in its entirety by and should be read in conjunction with the detailed information and financial statements incorporated by reference into this short form prospectus. This summary and the “Description of the Business” section that follows highlight selected information contained elsewhere in, or incorporated by reference into, this short form prospectus. You should read the entire short form prospectus and the information incorporated herein closely.

The Company is offering to exchange up to $600,000,000 aggregate principal amount of Initial Notes for an equal principal amount of Exchange Notes. In order to exchange your Initial Notes, you must validly tender them, as instructed herein and in the letter of transmittal. The Company will exchange all outstanding Initial Notes that are validly tendered and not validly withdrawn. The Company will issue the Exchange Notes as promptly as practicable after the expiration of the Exchange Offer.

Exchange Offer:

The Company will exchange your Initial Notes for an equal aggregate principal amount of Exchange Notes.

Resale of Exchange Notes:

Based on an interpretation by the staff of the SEC set forth in no-action letters issued to third parties, you may offer the Exchange Notes for resale, resell and otherwise transfer them without compliance with the registration or prospectus delivery provisions of the Securities Act if:

•

you are acquiring the Exchange Notes in the ordinary course of your business;

•

you are not participating, do not intend to participate and have no arrangement or understanding with any person to participate, in the distribution of the Exchange Notes issued to you; and

•

you are not an affiliate, under Rule 405 of the Securities Act, of the Company.

Each broker-dealer that receives Exchange Notes for its own account pursuant to the Exchange Offer must acknowledge that it will deliver a prospectus in connection with any resale of such Exchange Notes in the United States. The letter of transmittal states that by so acknowledging and by delivering a prospectus, a broker-dealer will not be deemed to admit that it is an “underwriter” within the meaning of the Securities Act. The letter of transmittal also includes an acknowledgment that each person participating in the Exchange Offer does not intend to engage in a distribution of the Exchange Notes. In addition, the letter of transmittal includes an acknowledgment for each person that is a broker-dealer in connection with resales of Exchange Notes received in exchange for Initial Notes where such Initial Notes were acquired by such broker-dealer as a result of market-making activities or other trading activities that such broker-dealer will satisfy any prospectus delivery requirements in connection with any resale of Exchange Notes received pursuant to the Exchange Offer. This short form prospectus, as it may be amended or supplemented from time to time, may be used by such broker-dealers for such prospectus delivery requirements. We have agreed that, for a period of 180 days after the Expiration Date (as defined herein), we will make this short form prospectus available to any broker-dealer for use in connection with any such resale. See “Plan of Distribution.”

Any holder of Initial Notes who is our affiliate, does not acquire Exchange Notes in the ordinary course of its business, or tenders its Initial Notes in the Exchange Offer with the intention to participate, or for the purpose of participating, in a distribution of Exchange Notes, cannot rely on the position

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of the staff of the SEC enunciated in Morgan Stanley & Co. Incorporated (available June 5, 1991) and Exxon Capital Holdings Corporation (available May 13, 1988), as interpreted in Shearman & Sterling (available July 2, 1993), or similar no-action letters and, in the absence of an exemption therefrom, must comply with the registration and prospectus delivery requirements of the Securities Act in connection with any resale of the Exchange Notes in the United States.

You should read the discussion under the heading “Exchange Offer” for further information regarding the Exchange Offer and resale of the Exchange Notes.

Registration Rights Agreement:

The Company has undertaken this Exchange Offer pursuant to the terms of a registration rights agreement entered into with the initial purchasers of the Initial Notes (the “Registration Rights Agreement”). See “The Exchange Offer”.

Consequences of Failure to Exchange Initial Notes:

You will continue to hold the Initial Notes that remain subject to their existing transfer restrictions if:

•

you do not tender your Initial Notes; or

•

you tender your Initial Notes and they are not accepted for exchange.

Subject to certain limited exceptions, the Company will have no obligation to register resales of the Initial Notes after the Company consummates the Exchange Offer. See “The Exchange Offer — Terms of the Exchange Offer — Consequences of Failure to Exchange” and “The Exchange Offer — Terms of the Exchange Offer — Acceptance of Initial Notes for Exchange; Delivery of Exchange Notes”.

Expiration Date:

The Expiration Date for the Exchange Offer is 5:00 p.m., New York City time, on , 2021, unless the Company extends it, in which case “Expiration Date” means 5:00 p.m., New York City time, on the date to which the Exchange Offer is extended.

Conditions to the Exchange Offer:

The Exchange Offer is subject to certain customary conditions, which the Company may waive. See “The Exchange Offer — Terms of the Exchange Offer — Conditions”.

Procedures for Tendering Initial Notes:

If you wish to accept the Exchange Offer, you must submit the required documentation and effect a tender of Initial Notes pursuant to the procedures for book-entry transfer (or other applicable procedures), all in accordance with the instructions described in this short form prospectus and in the relevant letter of transmittal. See “The Exchange Offer — Terms of the Exchange Offer — Procedures for Tendering”, “The Exchange Offer — Terms of the Exchange Offer — Book-Entry Transfer”, “The Exchange Offer — Terms of the Exchange Offer — Exchanging Book-Entry Notes” and “The Exchange Offer — Terms of the Exchange Offer — Guaranteed Delivery Procedures”.

Guaranteed Delivery Procedures:

If you wish to tender your Initial Notes, but cannot properly do so prior to the Expiration Date, you may tender your Initial Notes in accordance with the guaranteed delivery procedures described in “The Exchange Offer — Terms of the Exchange Offer — Guaranteed Delivery Procedures”.

Withdrawal Rights:

Tenders of Initial Notes may be withdrawn at any time prior to the Expiration Date. To withdraw a tender of Initial Notes, a written or facsimile transmission notice of withdrawal must be received by the exchange agent at its address set forth in the letter of transmittal prior to the Expiration Date.

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Acceptance of Initial Notes and Delivery of Exchange Notes:

Subject to certain conditions, any and all Initial Notes that are validly tendered in the Exchange Offer prior to the Expiration Date will be accepted for exchange. The Exchange Notes issued pursuant to the Exchange Offer will be delivered promptly following the Expiration Date. See “The Exchange Offer — Terms of the Exchange Offer — Acceptance of Initial Notes for Exchange; Delivery of Exchange Notes”.

U.S. Federal Income Tax Considerations:

The exchange of the Initial Notes for the Exchange Notes will not constitute a taxable exchange for U.S. federal income tax purposes. See “Certain U.S. Federal Income Tax Considerations”.

Use of Proceeds:

The Company will not receive any proceeds from the issuance of the Exchange Notes. The Company is offering the Exchange Notes solely to satisfy its obligations under the Registration Rights Agreement. Initial Notes that are validly tendered (and not validly withdrawn) and exchanged will be retired and cancelled and cannot be reissued. See “Use of Proceeds”.

Exchange Agent:

The Bank of New York Mellon is serving as the exchange agent.

Summary of Terms of the Exchange Notes:

The terms of the Exchange Notes are substantially identical to the terms of the Initial Notes except that the Exchange Notes:

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will have been issued in the Exchange Offer, which is being registered under the Securities Act, and therefore the Exchange Notes will not bear a legend containing restrictions on transfer;

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will not contain provisions relating to additional interest for any failure to comply with the Registration Rights Agreement;

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will bear a different CUSIP number from the Initial Notes; and

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will not entitle their holders to registration rights.

Issuer:

Fairfax Financial Holdings Limited

Exchange Notes Offered:

Up to $600,000,000 aggregate principal amount of 3.375% Senior Notes due 2031.

Maturity Date:

March 3, 2031

Interest:

3.375%. Interest is payable in semi-annual installments in arrears on each March 3 and September 3, commencing September 3, 2021.

Ranking:

The Exchange Notes will be direct, unsecured obligations of the Company. The Exchange Notes will rank equally and ratably with all of the Company’s other unsecured and unsubordinated indebtedness from time to time outstanding. The Exchange Notes will be effectively subordinated to any secured indebtedness of the Company to the extent of the assets securing such indebtedness. The Exchange Notes will also be structurally subordinated to all obligations of the Company’s subsidiaries. See “Risk Factors — Risk Factors Relating to the Exchange Notes”.

Payment of Additional Amounts:

Any payments made by the Company with respect to the Exchange Notes will be made without withholding or deduction for Canadian taxes unless required by law. Subject to certain exclusions, if the Company is required by law to withhold or deduct for Canadian taxes with respect to a payment to the holders of the Exchange Notes, the Company will pay the additional amount necessary so that the net amount received by the holders of the Exchange Notes after the withholding or deduction is not less than the amount that they would have received in the absence of the withholding or deduction. See “Description of the Notes — Payment of Additional Amounts”.

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Optional Redemption:

Prior to December 3, 2030 (the “Par Call Date”), the Company may redeem, in whole at any time or in part from time to time, the Exchange Notes at 100% of their principal amount, plus a “make whole” premium as described under the heading “Description of the Notes — Optional Redemption,” together with accrued and unpaid interest, if any, to, but excluding, the date of redemption. On or after the Par Call Date, the Company may redeem, in whole at any time or in part from time to time, the Exchange Notes at 100% of their principal amount together with accrued and unpaid interest, if any, to the date of redemption.

Redemption for Tax Reasons:

The Company may redeem, in whole, but not in part, the Exchange Notes in the event of certain changes in the tax laws of Canada that could require the Company to pay additional amounts as described under “Description of the Notes — Payment of Additional Amounts.” The redemption price would be equal to 100% of the principal amount of the Exchange Notes, together with accrued and unpaid interest on the Exchange Notes to be redeemed to the date of redemption. See “Description of the Notes — Redemption for Tax Reasons”.

Restrictive Covenants:

The Third Supplemental Indenture (as defined below) amended the indenture that will govern the Notes (as defined below) to eliminate or amend certain restrictive covenants of the Company. The Third Supplemental Indenture provides that certain covenants will be automatically eliminated or amended effective as of the first date (the “Amendment Date”) on which there are no securities outstanding of any series created pursuant to the indenture prior to the date of the Third Supplemental Indenture that are entitled to the benefit of such covenants, including in respect of the limitation on liens on capital stock of restricted subsidiaries described below. The Third Supplemental Indenture also provides that if the Company grants any security interest to any collateral agent or trustee pursuant to such covenant in connection with any series created after the date of the Third Supplemental Indenture, such security interest shall be automatically released on the Amendment Date and any such collateral agent or trustee shall be authorized to take such further actions as the Company may reasonably request to give effect to such release.

The Indenture governing the Exchange Notes contains covenants that, among other things, limit our ability to:

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until the Amendment Date, create liens on the capital stock of certain of our subsidiaries; and

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enter into specific mergers or consolidations or convey, transfer or lease our properties and assets substantially as an entirety.

See “Description of the Notes — Certain Covenants”.

Absence of Public Market for the Exchange Notes:

There is currently no established trading market for the Exchange Notes. The Company does not intend to apply for a listing of the Exchange Notes on any securities exchange or an automated dealer quotation system. Accordingly, there can be no assurance as to the development or liquidity of any market for the Exchange Notes and this may affect the pricing, transparency and availability of trading prices of the Exchange Notes.

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DESCRIPTION OF THE BUSINESS

Unless the context otherwise requires, the terms “Fairfax”, “Company”, “we”, “us” and “our” refer to Fairfax Financial Holdings Limited and its subsidiaries; the term “Allied World” refers to our majority-owned Bermuda-based global property, casualty and specialty insurance and reinsurance company, Allied World Assurance Company Holdings, Ltd and its subsidiaries; the term “Brit” refers to our majority-owned specialty insurance and reinsurance company operating in the Lloyd’s market, Brit Limited and its subsidiaries; the term “Bryte” refers to our wholly-owned South African property and casualty insurance business, Bryte Insurance Company Ltd.; the term “Colonnade” refers to our wholly-owned Luxembourg based insurance company, Colonnade Insurance S.A.; the term “Crum & Forster” refers to our wholly-owned U.S. property and casualty insurance business, Crum & Forster Holdings Corp. and its subsidiaries; the term “Fairfax Asia” refers to our property and casualty insurance business conducted through our subsidiaries in Hong Kong, Sri Lanka, Indonesia and Malaysia; the term “Fairfax Brasil” refers to our wholly-owned Brazilian property and casualty insurance company, Fairfax Brasil Seguros Corporativos S.A.; the term “Fairfax Latam” refers to our property and casualty insurance business conducted in Argentina, Chile, Colombia and Uruguay; the term “Fairfax Ukraine” refers to our property and casualty insurance business conducted through our subsidiaries in Ukraine; the term “Group Re” refers to our wholly-owned reinsurance business, conducted through certain other subsidiaries; the term “Hamblin Watsa” refers to our wholly-owned investment management subsidiary, Hamblin Watsa Investment Counsel Ltd.; the term “Northbridge” refers to our wholly-owned Canadian property and casualty insurance business, Northbridge Financial Corporation and its subsidiaries; the term “Odyssey Group” refers to our wholly-owned U.S. reinsurance and insurance business, Odyssey Group Holdings Inc. and its subsidiaries; the term “Polish Re” refers to our wholly-owned Polish reinsurance company, Polskie Towarzystwo Reasekuracji Spólka Akcyjna; the term “Zenith National” refers to our wholly-owned U.S. workers’ compensation insurance business, Zenith National Insurance Corp. and its subsidiaries; the term “Singapore Re” refers to our wholly-owned Singapore based general property and casualty reinsurance company, Singapore Reinsurance Corporation Limited; and the term “Eurolife” refers to our majority-owned Greek life and non-life insurer, Eurolife FFH Insurance Group Holdings S.A.

We are a holding company which, through our subsidiaries, is engaged in property and casualty insurance and reinsurance and the associated investment management. We are incorporated under the Canada Business Corporations Act. We operate through a decentralized operating structure, with autonomous management teams applying a focused underwriting strategy to our markets. We seek to differentiate ourselves by combining disciplined underwriting with the investment of our assets on a total return basis, which we believe provides above-average returns over the long-term. We provide a full range of property and casualty products, maintaining a diversified portfolio of risks across classes of business, geographic regions, and types of insureds. We have been under current management since September 1985. Our principal executive offices are located at Suite 800, 95 Wellington Street West, Toronto, Ontario, Canada M5J 2N7. Our telephone number is (416) 367-4941.

We conduct our business through the following segments, with each of our continuing operations maintaining a strong position in its respective markets.

Our reinsurance business is conducted through Odyssey Group, Group Re, Brit, Allied World, Polish Re and Singapore Re. Odyssey Group is a U.S. based underwriter of a full range of property and casualty reinsurance on a worldwide basis. Group Re primarily constitutes the participation by our wholly-owned subsidiaries CRC Reinsurance Limited, Wentworth Insurance Company Ltd. and Connemara Reinsurance Company Ltd. (all based in Barbados) in the reinsurance of Fairfax’s subsidiaries by quota share or through participation in those subsidiaries’ third party reinsurance programs on the same terms and pricing as the third party reinsurers. Group Re also writes third party business. Our majority-owned subsidiary Brit, based in the United Kingdom, is a market-leading global Lloyd’s of London specialty insurer and reinsurer. Allied World, our 70.9% owned subsidiary based in Bermuda, is a global property, casualty and specialty insurance and reinsurance company. Polish Re, based in Warsaw, Poland, writes reinsurance business in the Central and Eastern European regions. Singapore Re, based in Singapore, is a general reinsurance company providing reinsurance coverage in the Asia region. We also hold a 47.1% interest in Thai Reinsurance Public Company Limited (a provider of reinsurance and insurance services based in Bangkok, Thailand).

Our insurance business is conducted through Northbridge (Canadian insurance), Crum & Forster (U.S. property and casualty insurance), Zenith National (U.S. workers’ compensation insurance), Brit (United

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States, United Kingdom and international insurance), Allied World (North American and international insurance), Fairfax Asia (Asian insurance), Fairfax Latam (South American insurance), Bryte (South African insurance), Fairfax Brasil (Brazilian insurance), Colonnade (Central and Eastern European insurance), Fairfax Ukraine (Ukrainian property and casualty insurance) and Eurolife (Greek life and non-life insurance). Odyssey Group also conducts insurance business through its U.S. Insurance and London Market divisions. Northbridge provides commercial and personal lines property and casualty insurance primarily in Canada through a wide range of distribution channels. Crum & Forster provides a full range of commercial property and casualty insurance, which targets specialty classes of business that emphasize strong technical underwriting expertise. Zenith National is primarily engaged in the workers’ compensation insurance business in the United States. Odyssey Group provides a range of professional and specialty liability insurance in the United States and internationally through its U.S. Insurance and London Market divisions. Brit is a market-leading global Lloyd’s of London specialty insurer. Allied World is a market-leading global property, casualty and specialty insurer. Fairfax Asia is comprised of:

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our wholly-owned, Hong Kong-based subsidiary, Falcon Insurance Company (Hong Kong) Limited, which writes property and casualty insurance in niche markets in Hong Kong;

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our 85.0% owned, Malaysia-based subsidiary, The Pacific Insurance Berhad, which writes all classes of general insurance and medical insurance in Malaysia;

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our 80.0% owned, Jakarta-based subsidiary, PT Asuransi Multi Artha Guna Tbk, an Indonesian general insurance company;

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our 78.0% owned, Sri Lanka-based subsidiary, Fairfirst Insurance Limited, a Sri Lankan general insurance company;

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our 41.2% interest in Thailand-based Falcon Insurance PLC, a Thai property and casualty insurance company;

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our 35.0% interest in Bank for Investment and Development of Vietnam Insurance Joint Stock Corporation, a Vietnamese property and casualty insurance company; and

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our 49.0% interest in Go Digit Infoworks Services Private Limited, whose subsidiary, Go Digit Insurance Limited, is an Indian general insurance company.

Fairfax Latam, based in Miami, Florida, consists of insurance operations in Argentina, Chile, Colombia and Uruguay. Bryte, based in South Africa, writes property and casualty insurance in South Africa and Botswana. Fairfax Brasil, based in Brazil, writes commercial property and casualty business, with a primary focus on markets in Brazil. Colonnade, based in Luxembourg, writes business in the Central and Eastern regions of Europe. Fairfax Ukraine, our 70.0% owned subsidiary based in Ukraine, writes property and casualty insurance in Ukraine. Eurolife, our 80.0% owned subsidiary based in Greece, writes life and non-life insurance in Greece.

Our run-off business, comprised of the U.S. run-off group and, previously, our 60.0% joint venture interest in RiverStone (Barbados) Ltd. (“RiverStone Barbados”), includes our discontinued business that did not meet our underwriting criteria or strategic objectives and selected business previously written by our other subsidiaries that was put under dedicated run-off management. In addition, our run-off segment includes third-party run-off operations that we have acquired, which we believe will provide us with the opportunity to earn attractive returns on our invested capital. The U.S. run-off group (“U.S. Run-off”) is principally comprised of TIG Insurance Company. RiverStone Barbados was comprised of our former European run-off group (“European Run-off”) which principally consisted of RiverStone Insurance (UK) Limited, Syndicate 3500 at Lloyd’s (managed by RiverStone Managing Agency Limited), TIG Insurance (Barbados) Limited and Advent Capital (Holdings) Ltd. European Run-off was contributed to RiverStone Barbados on March 31, 2020 in exchange for a 60.0% joint venture interest and cash of $599.5 million. On August 23, 2021, we completed the sale of our 60.0% joint venture interest in RiverStone Barbados for proceeds of approximately $700 million.

Our Non-insurance companies reporting segment comprises Recipe Unlimited Corporation (“Recipe”), William Ashley China Corporation (“William Ashley”), Sporting Life Inc. (“Sporting Life”), Golf Town Limited (“Golf Town”), Kitchen Stuff Plus, Inc. (“Kitchen Stuff Plus”), Boat Rocker Media Inc. (“Boat Rocker”), Praktiker Hellas Commercial Societe Anonyme (“Praktiker”), Dexterra Group Inc. (“Dexterra

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Group”), AGT Food and Ingredients Inc. (“AGT”), Farmers Edge Inc. (“Farmers Edge”), Pethealth Inc. (“Pethealth”), Thomas Cook (India) Limited (“Thomas Cook India”) and its wholly-owned subsidiary Sterling Holiday Resorts (India) Limited (“Sterling Resorts”), and Fairfax India Holdings Corporation (“Fairfax India”) and its subsidiaries National Collateral Management Services Limited (“NCML”), Fairchem Organics Limited (“Fairchem”) and Saurashtra Freight Private Limited (“Saurashtra Freight”). Recipe franchises and/or operates restaurant brands across Canada and in select locations in the United States. William Ashley is a prestige retailer of exclusive tableware and gifts in Canada. Sporting Life is a Canadian retailer of sporting goods and sports apparel. Golf Town is one of the largest specialty retailers of golf equipment, consumables, golf apparel and accessories in Canada. Kitchen Stuff Plus is a Canadian retailer of housewares and home décor. Boat Rocker is a global content creator producing and distributing high quality and award winning entertainment for television, film, and digital. Praktiker is one of the largest home improvement and do-it-yourself goods retailers in Greece. Dexterra Group provides a range of industrial services, modular construction solutions, facilities management and operations solutions to industries and governments. AGT is a supplier of pulses, staple foods and food ingredients. Farmers Edge provides advanced digital tools to growers and other key participants in the agricultural value chain. Pethealth is headquartered in Canada and provides pet medical insurance, management software and pet-related database management services in North America and the United Kingdom. Thomas Cook India is an integrated travel and travel-related financial services company in India, offering a broad range of services that include foreign exchange, corporate and leisure travel and insurance. Sterling Resorts is engaged in vacation ownership and leisure hospitality and operates a network of resorts in India. Fairfax India invests in public and private equity and debt instruments in India and Indian businesses or other businesses primarily conducted in or dependent on India. NCML is a leading private-sector agricultural commodities storage company in India. Fairchem is a specialty chemical manufacturer in India of oleo chemicals used in the paints, inks and adhesives industries, as well as intermediate nutraceutical and health products. Saurashtra Freight operates a container freight station at the Mundra Port in the Indian state of Gujarat.

Our invested assets are managed by our wholly-owned investment management subsidiary, Hamblin Watsa. Hamblin Watsa has managed our invested assets since September 1985 and emphasizes a conservative investment philosophy, seeking to invest our assets on a total return basis, which includes realized and unrealized gains over the long-term, using a value-oriented approach.

Our insurance operations primarily use brokers to distribute their business and in some instances will distribute through agents or directly to the customer. They may also conduct business through third parties such as managing general agents where it is cost effective to do so and where we can control the underwriting process to ensure our risk management criteria are met. Our insurance operations have relationships with many different types of brokers including independent retail brokers, wholesale brokers and national brokers depending on the particular jurisdiction. Each of these channels has its own distinct distribution characteristics and customers. Our reinsurance operations are dependent primarily on a limited number of international reinsurance brokers.

Recent Developments

Repayment of Credit Facility

Subsequent to June 30, 2021 and up to the date hereof, we have fully repaid the outstanding balance of $500.0 million on our Credit Facility.

Sale of RiverStone Barbados to CVC Capital Partners (“CVC”)

On August 23, 2021, we sold our 60.0% joint venture interest in RiverStone Barbados to CVC Capital Partners (“CVC”). OMERS, the pension plan for Ontario’s municipal employees (“OMERS”), also sold its 40.0% joint venture interest in RiverStone Barbados to CVC as part of the transaction. We received proceeds of approximately $700 million from the sale and we are also entitled to receive up to $235.7 million in potential future proceeds pursuant to a contingent value instrument. Pursuant to the agreement with CVC, on February 8, 2021, we also entered into an arrangement with RiverStone Barbados and certain subsidiaries thereof to purchase (unless sold earlier) certain portfolio investments owned by RiverStone Barbados and certain subsidiaries thereof at specified prices totaling approximately $1.3 billion prior to the end of 2022.

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Certain subsidiaries of RiverStone Barbados beneficially own a portion of the Company’s indirect holdings in various Canadian reporting issuers and certain other companies. Accordingly, CVC and certain affiliates thereof became the indirect beneficial owner of a portion of those securities upon completion of the transaction. As part of the transaction, on February 8, 2021, the Company entered into Asset Value Loan Notes (“AVLNs”) with the current holders of such securities for purposes of assurance to CVC and certain affiliates thereof of the approximately $1.3 billion value of the securities until such time as the securities are purchased by or sold at the direction of Hamblin Watsa, prior to the end of 2022. The Company, through Hamblin Watsa, continues to manage and have direction over these securities.

Completion of OMERS’ Investment in Brit

On August 27, 2021, the Company sold an approximate 14% interest in Brit to OMERS for cash consideration of approximately $375 million. The Company will have the ability to repurchase OMERS’ interest in Brit over time.

COVID-19 pandemic

Given the uncertain and evolving situation resulting from COVID-19 including subsequent variants, it is difficult to predict the impact the pandemic will continue to have on the company’s businesses. The extent of the impact will depend on future developments including new information which may emerge concerning the severity of COVID-19 and additional actions which may be taken to contain COVID-19, including extending government mandated economic shutdowns, particularly as new variants emerge. COVID-19 has adversely affected the company’s operations across the various operating segments, with varying effects. The Company’s underwriting results in the second quarter and first six months of 2021 showed significant improvement from those in the second quarter and first six months of 2020, despite additional current period COVID-19 losses of $8.6 million and $28.0 million, and net adverse prior year reserve development of COVID-19 losses of $60.1 million and $87.1 million, primarily through business interruption exposures outside North America and event cancellation coverage. Additionally, the company expects its insurance and reinsurance operations to continue to experience a reduction in premiums written in certain segments where premiums are directly or indirectly linked to travel or economic activity, albeit these segments are beginning to modestly recover. Certain of the Company’s non-insurance operations continue to experience disruptions and increased uncertainty due to current economic conditions, particularly those in the restaurant, retail and hospitality sectors whose business volumes are directly linked to the re-opening of the economy in the jurisdictions in which they operate.

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RISK FACTORS

An investment in the Exchange Notes involves risk. You should carefully consider the following risk factors, as well as the information contained in and incorporated by reference into this short form prospectus, including the risks described in our annual information form for the year ended December 31, 2020, which is incorporated by reference in this short form prospectus, before deciding whether to participate in the Exchange Offer. Any of these risks could materially adversely affect our business, financial condition or results of operations and could materially adversely affect your investment in the Exchange Notes. Additional risks and uncertainties not currently known to us or that we currently deem to be immaterial may also materially and adversely affect our business, financial condition or results of operations.

Risk Factors Relating to Our Business

We expect to continue to be adversely impacted by the COVID-19 pandemic.

The rapid spread of the COVID-19 virus, which was declared by the World Health Organization to be a pandemic on March 11, 2020, and actions taken globally in response to COVID-19, have significantly disrupted business activities throughout the world. Our business relies, to a certain extent, on free movement of goods, services, and capital from around the world, which has been significantly restricted as a result of COVID-19. Although we are able to have our insurance businesses remain open during the pandemic, the businesses of many of our insureds have been impacted, resulting in increased counterparty risk. We increased our leverage under our $2.0 billion unsecured revolving credit facility entered into by Fairfax and a syndicate of lenders (the “Credit Facility”) as it added liquidity support for our insurance and reinsurance companies should it be needed during the pandemic. In addition, we experienced losses related to our equity investment portfolio as well as certain assets impairments that adversely impacted our financial results for the first six months of 2021, and we anticipate that our future results of operations may also be negatively impacted by the economic effects of the pandemic.

Given the ongoing and dynamic nature of the circumstances surrounding COVID-19, it is difficult to predict how significant the impact of COVID-19, including any responses to it, will be on the global economy and our businesses, investments and employees in particular, or for how long any disruptions are likely to continue. The extent of such impact will depend on future developments, which are highly uncertain, rapidly evolving and difficult to predict, including new information which may emerge concerning the severity of COVID-19 and additional actions which may be taken to contain COVID-19, including the distribution of vaccines, as well as the timing of the re-opening of the economy in various parts of the world. Such further developments could have a material adverse effect on our business, financial condition, results of operations and cash flows.

The slowdown in the global economy as a result of COVID-19 has adversely affected our operating segments to varying degrees. Underwriting results in 2020 and the first six months of 2021 were negatively affected by COVID-19 losses, primarily from international business interruption exposures and event cancellation coverage, and we expect our insurance and reinsurance operations to experience a reduction in premiums written in certain segments where premiums are directly or indirectly linked to economic activity. In addition, certain government officials, including U.S. state insurance commissioners, have taken actions to protect consumers and specified classes of workers from hardship caused by COVID-19 which in the aggregate may adversely affect our operating results in the near term. While it is likely that certain insurance and reinsurance lines of business may experience increased loss activity due to COVID-19, there are also many that will likely experience improved loss experience due to reduced exposures to loss. Certain of our non-insurance operations continue to experience reductions in revenue due to current economic conditions, particularly those in the restaurant, retail and hospitality sectors whose business volumes are directly linked to the re-opening of the economy in the jurisdictions in which they operate. The ultimate impact of COVID-19 on us will not be fully known for many months, perhaps years.

If our actual claims exceed our claim reserves, our financial condition and results of operations could be adversely affected.

We maintain reserves to cover our estimated ultimate unpaid liability for losses and loss adjustment expenses with respect to insurance and reinsurance policies underwritten by the company at the end of each

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accounting period. Our success is dependent upon our ability to accurately assess the risks associated with the businesses that we reinsure or insure. If we fail to accurately assess the risks we assume, we may fail to establish appropriate premium rates and our reserves may be inadequate to cover our losses, which could have a material adverse effect on our financial condition and reduce our net earnings.

At June 30, 2021, we had gross provision for losses and loss adjustment expenses of $32.4 billion. Due to the ongoing and developing COVID-19 pandemic, our gross provision for losses and loss adjustment expenses may be greater for future financial losses. This could adversely affect our net earnings and financial condition in future reporting periods.

Reserves do not represent an exact calculation of liability, but instead represent estimates at a point in time involving actuarial and statistical projections of our expectations of the ultimate settlement of claims incurred and the associated claims adjustment expense. Establishing an appropriate level of claims reserves is an inherently uncertain process. We utilize both proprietary and commercially available actuarial models, as well as historical insurance industry loss development patterns, to assist in the establishment of appropriate claim reserves.

In contrast to casualty losses, which frequently can be determined only through lengthy and unpredictable litigation, property losses tend to be reported promptly and usually are settled within a shorter period of time. Nevertheless, for both casualty and property losses, actual claims and claim expenses ultimately paid may deviate, perhaps substantially, from the reserve estimates reflected in our financial statements. Variables in the reserve estimation process can be affected by both internal and external events, such as changes in claims handling procedures, economic and social inflation, legal trends and legislative changes, and our reserve estimates may be impacted materially by the ongoing COVID-19 pandemic. Many of these items are not directly quantifiable, particularly on a prospective basis.

If our claim reserves are determined to be inadequate, we will be required to increase claim reserves with a corresponding reduction in our net earnings in the period in which the deficiency is rectified. It is possible that claims in respect of events that have occurred could exceed our claim reserves and have a material adverse effect on our results of operations in a particular period and/or our financial condition.

Even though most insurance contracts have policy limits, the nature of property and casualty insurance and reinsurance is such that losses can exceed policy limits for a variety of reasons and could significantly exceed the premiums received on the underlying policies. When this occurs, our financial results are adversely affected.

Unpredictable catastrophic events could reduce our net earnings.

Our insurance and reinsurance operations expose us to claims arising out of catastrophes. We have experienced, and will in the future experience, catastrophe losses which may materially reduce our profitability or harm our financial condition. Catastrophes can be caused by various events, including natural events such as hurricanes, windstorms, earthquakes, tornadoes, hailstorms, severe winter weather and fires, and unnatural events such as terrorist attacks and riots. Weather-related losses have increased in recent years, in part due to climate change which represents a significant emerging risk that will continue to increase the inherent unpredictability of both the frequency and severity of weather-related catastrophe losses.

The extent of losses from a catastrophe is a function of both the total amount of insured exposure in the area affected by the event and the severity of the event. Most catastrophes are restricted to small geographic areas; however, hurricanes, windstorms and earthquakes may produce significant damage in large, heavily populated areas. Catastrophes can cause losses in a variety of property and casualty lines, including losses relating to business interruptions occurring in the same geographic area as the catastrophic event or in the other geographic areas. It is possible that a catastrophic event or multiple catastrophic events could have a material adverse effect upon our financial condition, profitability or cash flows.

We believe that increases in the value and geographic concentration of insured property, higher construction costs due to labor and raw material shortages following a significant catastrophic event could increase the number and severity of claims from catastrophic events in the future.

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Our portfolio holdings are subject to fluctuations in the market which could negatively affect their value. If we are unable to realize our investment objectives, our business, financial condition or results of operations may be adversely affected.

Investment returns are an important part of our overall profitability and our operating results depend in part on the performance of our investment portfolio. We hold bonds and other debt instruments, common stocks, preferred stocks, and derivative instruments in our portfolio.

Accordingly, fluctuations in the fixed income or equity markets could have an adverse effect on our financial condition, profitability or cash flows. We derive our investment income from interest and dividends, together with net gains or losses on investments. The portion derived from net gains or losses on investments generally fluctuates from year to year. For the six months ended June 30, 2021, net gains on investments accounted for 86.5% of our total investment income (including net gains on investments). Net gains on investments are typically a less predictable source of investment income than interest and dividends, particularly in the short term.

The return on our portfolio and the risks associated with our investments are also affected by our asset mix, which can change materially depending on market conditions. Investments in cash or short-term investments generally produce a lower return than other investments. The market value of bonds, other debt instruments and preferred stocks fluctuates with changes in interest rates and credit quality, and is exposed to liquidity risks. The market value of common stocks and equity-related securities is exposed to fluctuations in the stock market and to liquidity risk. Equities, equity-related securities and derivative securities are volatile or extremely volatile, with the result that their market value and their liquidity may vary dramatically either up or down in short periods, and their ultimate value will therefore only be known upon their disposition or settlement.

The uncertainty around the ultimate amount and the timing of our claim payments may force us to liquidate securities, which may cause us to incur losses. If we structure our investments improperly relative to our liabilities, we may be forced to liquidate investments prior to maturity at a significant loss to cover such liabilities. Realized and unrealized investment losses resulting from a decline in value could significantly decrease our net earnings.

The ability to achieve our investment objectives is affected by general economic conditions that are beyond our control, which includes the ongoing and developing COVID-19 pandemic. General economic conditions can adversely affect the markets for interest-rate-sensitive securities, including the extent and timing of investor participation in such markets, the level and volatility of interest rates and, consequently, the value of fixed income securities. Interest rates are highly sensitive to many factors, including governmental monetary policies, domestic and international economic and political conditions and other factors beyond our control. General economic conditions, stock market conditions, environmental conditions, climate change and many other factors can also adversely affect the equity markets and, consequently, the value of the equity securities we own.

In addition, defaults by third parties who fail to pay or perform on their obligations could reduce our investment income and net gains on investment or result in investment losses. These defaults may be more substantial as a result of the economic disruption caused by the COVID-19 pandemic. We may not be able to realize our investment objectives, which could reduce our net earnings significantly and adversely affect our business, financial condition or results of operations.

The cycles of the insurance and reinsurance industries and general economic conditions may cause fluctuations in our operating results.

Historically, we have experienced fluctuations in operating results due to competition, frequency or severity of both catastrophic and non-catastrophic events, levels of capital and underwriting capacity, general economic conditions and other factors. Demand for insurance and reinsurance is influenced significantly by underwriting results of primary insurers and prevailing general economic conditions. Factors such as changes in the level of employment, wages, consumer spending, business investment and government spending, the volatility and strength of the global capital markets and inflation or deflation, as well as other global events

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such as the COVID-19 pandemic, all affect the business and economic environment and, ultimately, the demand for insurance and reinsurance products, and therefore may affect our net earnings, financial position or cash flows.

The property and casualty insurance business historically has been characterized by periods of intense price competition due to excess underwriting capacity, as well as periods when shortages of underwriting capacity have permitted attractive premium levels. We expect to continue to experience the effects of this cyclicality, which, during down periods, could significantly reduce the amount of premium we write and could harm our financial condition, profitability or cash flows. See “— Actions taken by government officials to protect businesses and individuals affected by the COVID-19 pandemic may adversely affect our business, financial condition or results of operations” below for more information.

In the reinsurance industry, the supply of reinsurance is related to prevailing prices and levels of underwriting capacity surplus that, in turn, may fluctuate in response to changes in rates of return being realized in the broader capital markets. If premium rates change or other reinsurance policy terms and conditions change expanding coverage, particularly if the present level of demand for reinsurance decreases because insurers require less reinsurance or the level of supply of reinsurance increases as a result of capital provided by existing reinsurers or alternative forms of reinsurance capacity enter the market, the profitability of our reinsurance business could be adversely affected.

Our business could be harmed because of our potential exposure to asbestos, environmental and other latent claims.

We have established loss reserves for asbestos and environmental and other latent claims that represent our best estimate of ultimate claims and claims adjustment expenses based upon all known facts and current law. As a result of significant issues surrounding liabilities of insurers, risks inherent in major litigation and diverging legal interpretations and judgments in different jurisdictions, actual liability for these types of claims could exceed the loss reserves set by us by an amount that could be material to our financial condition, profitability or cash flows in future periods.

We cannot assure you that our reinsurers and certain insureds will pay us on a timely basis or at all.

Most insurance and reinsurance companies reduce their exposure to any individual claim by reinsuring amounts in excess of their maximum desired retention. Reinsurance is an arrangement in which an insurer, called the cedant, transfers insurance risk to another insurer, called the reinsurer, which accepts the risk in return for a premium payment. This third party reinsurance does not relieve us, as a cedant, of our primary obligation to the insured. At June 30, 2021, we had a total of $11.6 billion recoverable from reinsurers. We cannot assure you that our reinsurers will pay our reinsurance claims on a timely basis or at all. Recoverable from reinsurers balances may become uncollectible due to reinsurer insolvency and credit concerns, due to the potentially long time period over which claims may be paid and the resulting recoveries may be received from the insurers, or due to policy disputes. As well, we bear credit risk with respect to our reinsurers (including retrocessionaires), both with respect to receivables reflected on our balance sheet as well as to contingent liabilities with respect to reinsurance protection on future claims. If reinsurers are unwilling or unable to pay us amounts due under reinsurance contracts, we will incur unexpected losses and our results of operations, financial condition and cash flows could be adversely affected.

We are exposed to credit risk in the event our insureds, insurance producers or reinsurance intermediaries fail to remit premiums that are owed to us or failure by our insureds to reimburse us for deductibles that are paid by us on their behalf.

We write certain insurance policies, such as large deductible policies (policies where the insured retains a specific amount of any potential loss), in which the insured must reimburse us for certain losses. Accordingly, we bear credit risk on these policies and cannot assure you that our insureds will pay us on a timely basis or at all. Our credit risk to insureds may also be substantially increased as a result of COVID-19. In the ordinary course of business we are sometimes unable to collect all amounts billed to insureds, generally due to disputes on audit of retrospectively rated policies and, in some cases, due to insureds having filed for bankruptcy protection. In addition, if an insured files for bankruptcy, we may be unable to recover on assets such insured may have pledged to us as collateral, and many of our insureds may face bankruptcy as a result of COVID-19.

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If our insurance and reinsurance subsidiaries are unable to maintain financial strength ratings, it may be more difficult for them to renew policies, retain business or write new business and a downgrade of our credit rating may affect the cost and availability of financing.

Financial strength and credit ratings by major North American rating agencies are important factors in establishing competitive position for insurance and reinsurance companies. Third-party rating agencies assess and rate the claims-paying ability of reinsurers and insurers based upon the criteria of such rating agencies. Periodically the rating agencies evaluate our insurance and reinsurance subsidiaries to confirm that they continue to meet the criteria of the ratings previously assigned to them. The claims-paying ability ratings assigned by rating agencies to insurance or reinsurance companies represent independent opinions of financial strength and ability to meet policyholder obligations.

A downgrade in these ratings could lead to a significant reduction in the number of insurance policies our insurance subsidiaries write and could cause early termination of contracts written by our reinsurance subsidiaries or a requirement for them to post collateral at the direction of their counterparties. Although we have not experienced any downgrades resulting from COVID-19 as of the date of this short form prospectus, we can provide no assurance that we will not experience such downgrades in the future.

A downgrade in our long-term debt ratings by the major rating agencies could require us and/or our subsidiaries to accelerate our or their cash settlement obligations for certain derivative transactions to which we or they are a party, and could result in the termination of certain other derivative transactions. In addition, a downgrade of our credit rating may affect the cost and availability of unsecured financing. Ratings are subject to periodic review at the discretion of each respective rating agency and may be revised downward or revoked at their sole discretion. Rating agencies may also increase their scrutiny of rated companies, revise their rating standards or take other action. We have dedicated personnel that manage our relationships with our various rating agencies, however there can be no assurance that these activities will avoid a downgrade by rating agencies.

We may not be successful in achieving our strategic objectives.

We may periodically and opportunistically acquire other insurance and reinsurance companies or execute other strategic initiatives developed by management. Although we undertake due diligence prior to the completion of an acquisition, it is possible that unanticipated factors could arise and there is no assurance that the anticipated financial or strategic objectives following an integration effort or the implementation of a strategic initiative will be achieved, which could adversely affect our financial condition, profitability or cash flows. In addition, our acquisition strategy may be negatively impacted by the adverse economic circumstances arising out of the COVID-19 pandemic.

We may periodically explore opportunities to make strategic investments in all or part of certain businesses or companies. Acquisitions may involve a number of special risks, including failure to retain key personnel, unanticipated events or circumstances and legal liabilities, some or all of which could have a material adverse effect on our business, results of operations and financial position. We cannot be sure that any acquired businesses will achieve the anticipated revenues, income and synergies, and our recently acquired businesses may fail to perform as previously anticipated as a result of the economic disruption caused by the COVID-19 pandemic. Failure on our part to manage our acquisition strategy successfully could have a material adverse effect on our business, results of operations and financial position. We cannot be sure that we will be able to identify appropriate targets, profitably manage additional businesses or successfully integrate any acquired business into our operations.

The strategies and performance of our subsidiaries, and the alignment of those strategies throughout our organization, are regularly assessed through various processes undertaken by senior management and our Board of Directors, however there can be no assurance that these efforts will be successful to mitigate the risks identified above.

We may hold derivative instruments, which could result in significant losses and volatility of our operating results.

We may hold significant investments in derivative instruments and the market value and liquidity of these investments are volatile or extremely volatile and may vary dramatically up or down in short periods, and

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these circumstances may be exacerbated by the COVID-19 pandemic. We may use derivative instruments to manage or reduce risks or as a cost-effective way to synthetically replicate the investment characteristics of an otherwise permitted investment. The market value and liquidity of these instruments are volatile and may vary dramatically up or down in short periods, and their ultimate value will therefore only be known upon their disposition or settlement. If the counterparties to our derivative instruments fail to honor their obligations under the derivative instrument agreements, we may lose the value of our derivative instruments. This failure could have an adverse effect on our financial condition and results of operations.

Our use of derivative instruments is governed by our investment policies and exposes us to a number of risks, including credit risk, interest rate risk, liquidity risk, inflation risk, market risk, basis risk and counterparty risk, although these risks are diminished because our principal use of derivative instruments is to hedge exposures to various risks. Counterparty risk is the risk that the other party to a derivative instrument will default on its contractual obligations. Counterparty risk may be substantially greater in the context of the COVID-19 pandemic.

We endeavor to limit counterparty risk through diligent selection of counterparties to our derivative instruments and through the terms of agreements negotiated with our counterparties. Pursuant to these agreements, we and the counterparties are required to deposit eligible collateral in collateral accounts for either the benefit of us or the counterparty depending on the then current fair value or change in the fair value of the derivative contract.

We may not be able to realize our investment objectives with respect to derivative instruments, which could have a material adverse effect on our financial position, profitability or cash flows.

The methods we employ to hedge risks associated with certain of our financial instruments may fail to achieve their desired risk management objectives.

We may use derivative instruments from time to time to manage or reduce our exposure to credit risk and various market risks, including interest rate risk, equity market risk, inflation/deflation risk and foreign currency risk. Our hedging strategies may be implemented to hedge risks associated with a specific financial instrument, asset or liability or at a macro level to hedge systemic financial risk and the impact of potential future economic crisis and credit related problems on our operations and the value of our financial assets. Credit default swaps, total return swaps and consumer price index-linked derivative instruments have been used in the past to hedge our macro-level risks, and accordingly, we may be substantially exposed to these risks to the extent they may increase in the context of the COVID-19 pandemic.

Our derivative instruments may expose us to basis risk. Basis risk is the risk that the fair value or cash flows of derivative instruments applied as economic hedges will not experience changes in exactly the opposite directions from those of the underlying hedged exposure. This imperfect correlation may adversely impact the net effectiveness of the hedge and may diminish the financial viability of maintaining the hedging strategy and therefore adversely impact our financial condition, profitability or cash flows.

We regularly monitor the prospective and retrospective effectiveness of our economic hedging instruments and will adjust the amount and/or type of hedging instruments as required to achieve our risk management goals.

We operate in a highly competitive environment which could make it more difficult for us to attract and retain business.

The property and casualty insurance industry and the reinsurance industry are both highly competitive, and likely will remain highly competitive in the foreseeable future. Competition in our industry is based on many factors, including premiums charged and other terms and conditions offered, products and services provided, commission structure, financial ratings assigned by independent rating agencies, speed of claims payment, reputation, selling effort, perceived financial strength and the experience of the insurer or reinsurer in the line of insurance or reinsurance to be written. We compete, and will continue to compete, with a large number of Canadian, U.S. and foreign insurers and reinsurers, as well as certain underwriting syndicates, some of which have greater financial, marketing and management resources than we do.

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In addition, some financial institutions, such as banks, are now able to offer services similar to those offered by our reinsurance subsidiaries while in recent years, capital market participants have also created alternative products that are intended to compete with reinsurance products.

Consolidation within the insurance industry could result in insurance and insurance market participants using their market power to implement price reductions. If competitive pressures compel us to reduce our prices, our operating margins would decrease. As the insurance industry consolidates, competition for customers could become more intense and the importance of acquiring and properly servicing each customer will become greater, causing us to incur greater expenses relating to customer acquisition and retention and further reducing operating margins.

Emerging claim and coverage issues, or the failure of any of the loss limitation methods we employ, could adversely affect our business, financial condition or results of operations.

The provision for claims is an estimate and may be found to be deficient, perhaps very significantly, in the future as a result of unanticipated frequency or severity of claims or for a variety of other reasons including unpredictable judicial rulings, expansion of insurance coverage to include exposures not contemplated at the time of policy issue (as was the case with asbestos and pollution exposures), extreme weather events, civil unrest and other macro-level events, such as the ongoing and developing COVID-19 pandemic. Unanticipated developments in the law as well as changes in social and environmental conditions could result in unexpected claims for coverage under insurance and reinsurance contracts. With respect to casualty lines of business, these legal, social and environmental changes may not become apparent until some time after their occurrence.

The full effects of these and other unforeseen emerging claim and coverage issues are extremely hard to predict and could harm our business. As a result, the full extent of our liability under our coverages, and in particular our casualty insurance policies and reinsurance contracts, may not be known until many years after a policy or contract is issued. Our exposure to this uncertainty is greatest in our “long-tail” casualty lines of business where claims can typically be made for many years, rendering them more susceptible to these trends than in the property insurance lines of business, which are more typically “short-tail.” In addition, we could be adversely affected by the growing trend of plaintiffs targeting participants in the property-liability insurance industry in purported class action litigation relating to claims handling and other practices.

Although loss exposure is limited by geographic diversification and we seek to limit our loss exposure by employing a variety of policy limits and other terms and conditions and through prudent underwriting of each program written, there can be no assurance that such measures will be successful in limiting our loss exposure.

We are a holding company and may not have access to the cash that is needed to meet our financial obligations.

We are a holding company that conducts substantially all of our business through our subsidiaries and receive substantially all of our earnings from them. We control the operating insurance and reinsurance companies, each of which must comply with applicable insurance regulations of the jurisdictions in which it operates. Each operating company must maintain reserves for losses and loss adjustment expenses to cover the risks it has underwritten.

Although substantially all of our operations are conducted through our subsidiaries, none of our subsidiaries are obligated to make funds available to us for the payment of principal and interest on our outstanding debt. Accordingly, our ability to meet financial obligations, including the ability to make payments on outstanding debt, is dependent on the distribution of earnings from our subsidiaries. The ability of subsidiaries to pay dividends in the future will depend on their statutory surplus, on earnings and on regulatory restrictions. Our subsidiaries may incur additional indebtedness that may severely restrict or prohibit the making of distributions, the payment of dividends or the making of loans by our subsidiaries to the Company. We cannot assure you that the agreements governing the current and future indebtedness of our subsidiaries will permit our subsidiaries to provide us with sufficient dividends, distributions or loans to meet our financial obligations, including to fund payments on our outstanding debt, or the Exchange Notes, when due. Dividends, distributions or returns of capital to us are subject to restrictions set forth in the insurance laws and regulations of the countries where the company operates (principally the U.S., Canada, the United Kingdom and Bermuda) (in each case, including the provinces, states or other jurisdictions therein) and is

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affected by the subsidiaries’ credit agreements and indentures, rating agencies, the discretion of insurance regulatory authorities and capital support agreements with subsidiaries. Although we strive to be soundly financed and maintain high levels of liquid assets, an inability of subsidiaries to pay dividends could have a negative impact on our liquidity and ability to meet its obligations.

Our inability to obtain additional capital in the future as required could have a material adverse effect on our financial condition.

Our future capital requirements depend on many factors, including our ability to successfully write new business successfully and to establish premium rates and reserves at levels sufficient to cover losses. Our liquidity needs could increase materially and rapidly for a variety of reasons, many of which are outside of our control. For example, our insurance subsidiaries may require us to make additional investments in the event that their regulatory capital levels decline below desired levels as a result of future impairments of investment securities, catastrophe losses or other conditions, including changes in regulatory capital requirements. We may need to make such additional investments as a result of impairments and losses attributable to COVID-19, and such investments may be substantial. To the extent that the funds generated by our business are insufficient to fund future operations, we may need to raise additional funds through equity or debt financings. Any equity or debt financing, if available at all, may be on terms that are not favorable to us. The cost and availability of debt financing is affected by credit ratings. Our ability to raise additional capital may be adversely affected by our credit ratings. If we cannot obtain adequate capital or if we fail to refinance our existing debt as it comes due, our business, financial condition and profitability would be materially adversely affected.

Our ability and/or the ability of our subsidiaries to obtain additional financing for working capital, capital expenditures or acquisitions in the future may also be limited under the terms of our Credit Facility. The Credit Facility contains various covenants that may restrict, among other things, our ability or the ability of our subsidiaries to incur additional indebtedness, to create liens or other encumbrances and to sell or otherwise dispose of assets and merge or consolidate with another entity. In addition, the Credit Facility contains certain financial covenants that require us to maintain a ratio of consolidated debt to consolidated capitalization not exceeding 0.35:1 and consolidated shareholders’ equity of not less than $9.5 billion, both calculated as defined in the financial covenants. A failure to comply with the obligations and covenants under the Credit Facility could result in an event of default under such agreement which, if not cured or waived, could permit acceleration of indebtedness, including other indebtedness of the Company or our subsidiaries. If such indebtedness were to be accelerated, there can be no assurance that our assets would be sufficient to repay that indebtedness in full.

Our business could be adversely affected by the loss of one or more key employees.

We are substantially dependent on a small number of key employees, including our Chairman and significant shareholder, Mr. Prem Watsa and the senior management of the Company and its operating subsidiaries. The industry experience and reputation of these individuals are important factors in our ability to attract new business and investment opportunities. Our success has been, and will continue to be, dependent on our ability to retain the services of our existing key employees and to attract and retain additional qualified personnel in the future. The loss of the services of any of these key employees, or the inability to identify, hire and retain other highly qualified personnel in the future could adversely affect the quality and profitability of our business operations. At the operating subsidiaries, employment agreements have been entered into with key employees. We do not maintain key employee insurance with respect to any of our employees.

We may be unable to obtain reinsurance coverage at reasonable prices or on terms that adequately protect us.

We use reinsurance arrangements, including reinsurance of our own reinsurance business purchased from other reinsurers, referred to as retrocessionaires, to help manage our exposure to property and casualty risks. The availability of reinsurance and rates charged by reinsurers are subject to prevailing market conditions, both in terms of price and available capacity, which can affect our business volume and profitability. Reinsurance companies can also add or exclude certain coverages from, or alter terms in, the policies that we purchase from them. Some exclusions are with respect to risks which we cannot exclude in policies we write due to business or regulatory constraints, such as coverage with respect to acts of terrorism, mold and cyber

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risk, and there can be no assurance that any losses attributable to the COVID-19 pandemic that we are required to pay would be covered by our reinsurance/retrocessions. Reinsurers may also impose terms, such as lower per occurrence and aggregate limits, on primary insurers that are inconsistent with corresponding terms in the policies written by these primary insurers. As a result, our insurance subsidiaries, like other primary insurance companies, increasingly are writing insurance policies which to some extent do not have the benefit of reinsurance protection. These gaps in reinsurance protection expose us to greater risk and greater potential losses. If we cannot obtain adequate reinsurance protection for the risks we underwrite, we may be exposed to greater losses from those risks or we may be forced to reduce the amount of business we underwrite, which will reduce our revenues. As a result, our inability to obtain adequate reinsurance protection could have a material adverse effect on our financial condition and operations.

The rates charged by reinsurers and the availability of reinsurance to our subsidiaries will generally reflect the recent loss experience of the Company and of the industry overall. Reinsurance pricing has continued to firm as a result of catastrophe losses in recent years, the effects of social inflation in the United States and the low interest rate environment. The retrocession market continues to experience the significant rate increases due to increased catastrophe activity in recent years. Each of our insurance and reinsurance subsidiaries continue to evaluate the relative costs and benefits of accepting more risk on a net basis, reducing exposure on a direct basis, and paying additional premiums for reinsurance.

Our operations could be adversely affected as a result of regulatory, political, economic or other influences in the insurance and reinsurance industries.

We are subject to government regulation in each of the jurisdictions in which our operating insurance and reinsurance subsidiaries are licensed or authorized to conduct business. Governmental bodies have broad administrative power to regulate many aspects of the insurance business, which may include accounting methods, governance, premium rates, market practices, policy forms, and capital adequacy. The laws and rules behind this regulation are concerned primarily with the protection of policyholders rather than investors. Governmental bodies may impose fines, additional capital requirements or limitations on our insurance and reinsurance operations, and/or impose criminal sanctions for violation of regulatory requirements. The laws and regulations that are applicable to our insurance and reinsurance operations are complex and may increase the costs of regulatory compliance or subject our business to the possibility of regulatory actions or proceedings.

In recent years, the insurance industry has been subject to increased scrutiny by legislatures and regulators alike. New laws and rules and new interpretations of existing laws and rules could adversely affect our financial results by limiting our operating insurance subsidiaries’ ability to make investments consistent with our total return strategy or requiring us to maintain capital in specific operating subsidiaries in excess of the amounts we consider to be appropriate, or causing us to make unplanned modifications of products or services, or imposing restrictions on our ability to enter or exit lines of insurance business or to utilize new methods of assessing and pricing risks or selling products and services. We cannot predict the future impact of changing law or regulation on our operations; any changes could have a material adverse effect on us or the insurance industry in general.

Actions taken by government officials to protect businesses and individuals affected by the COVID-19 pandemic may adversely affect our business, financial condition or results of operations.

Various government officials, including U.S. state insurance commissioners, have taken actions to protect consumers from hardship caused by COVID-19 and related stay-in-place measures that affect the insurance premiums and benefits payable under insurance policies and reinsurance contracts sold by our insurance subsidiaries. Regulators and legislatures may take additional future actions to protect consumers against hardship and some of these actions may have a material effect on our operating results.

In response to the COVID-19 pandemic, officials in many U.S. states issued orders that imposed moratoria for a specified time on the cancellation, non-renewal or termination of insurance policies due to non-payment of premiums. These orders applied for designated classes of policyholders and some required insurers to offer plans for deferred payment of such premiums without charging interest. Other U.S. states

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have issued guidance requesting insurers to voluntarily exercise forbearance on such cancellations, non-renewals and terminations. Such forbearance and future moratoria may disrupt the normal cash flows of our insurance operations and result in an increase in uncollected insurance premiums.

The state insurance commissioners of California and New Jersey each issued orders directing insurers to refund a portion of insurance premiums they have charged policyholders in their respective states for specified lines of insurance, including certain commercial lines written by our insurance subsidiaries, commensurate with the reduced levels of activity caused by the state-wide “shelter-in-place” orders issued in California and New Jersey. Other U.S. states may order similar refunds or reductions in premiums and/or disallow rate increases due to reduced exposures from reduced economic and physical activity and hardship to consumers. Other U.S. states have urged insurers to pay refunds or reduce premiums voluntarily. These measures, and the competitive pressures caused by voluntary reductions by other insurers, may affect our pricing and premium revenue.

In addition, officials in some U.S. states have declared, or proposed rules or legislation that declares, COVID-19 infections sustained by specified classes of workers, such as first responders, healthcare workers and workers who continue to work during the healthcare emergency because they are deemed “essential,” to be workplace injuries that are compensable under workers’ compensation laws and policies. This may require payment of workers’ compensation benefits for COVID-19 infections that were not contemplated in the pricing of our policies.

Most business owners and commercial property policies do not cover business interruption losses caused by the COVID-19 pandemic and related stay-in-place measures. Lawsuits have been filed by policyholders in different U.S. courts seeking coverage for lost income due to COVID-19 and resulting stay-in-place orders. While the defendant insurers in these cases have expressed that such losses are not covered, some courts have found in favor of policyholders. Policyholders may also assert novel theories of coverage and insurers may incur significant expense due to the pendency of a large number of individual suits. In addition, legislation has been introduced in several U.S. states which, if enacted, would require retroactive coverage of business interruption claims stemming from COVID-19 even if such loss is not covered under the terms of their policies or, going forward, require insurers providing business interruption coverage to cover losses from pandemics in their policies. Insurance regulators in some states will not approve policy exclusions for losses from COVID-19, viruses or pandemics. Many of these proposals for retroactive coverage provide for reimbursement of such payments through surcharges imposed on other insurers. However, the details of such reimbursement schemes have not been fully developed, and there is no assurance if such laws are enacted that insurers would be fully and promptly compensated for such payments and that surcharges would be evenly and fairly distributed across the insurance industry. There have also been U.S. Federal legislative proposals that would establish a Federal facility for covering business interruption losses resulting from a public health emergency. The effect of any such legislation, if enacted, on insurers that write commercial insurance policies cannot be assessed at the present time.

Our international business is subject to applicable laws and regulations relating to sanctions and foreign corrupt practices, the violation of which could adversely affect our operations.

We must comply with all applicable economic sanctions and anti-bribery laws and regulations, including those of Canada, the United States, the United Kingdom, the European Union and other foreign jurisdictions where we operate. U.S. laws and regulations applicable to us include the economic trade sanctions laws and regulations administered by the U.S. Department of the Treasury’s Office of Foreign Assets Control, as well as certain laws administered by the U.S. Department of State. In addition, our business is subject to the Foreign Corrupt Practices Act and other anti-bribery laws such as the U.K. Bribery Act that generally bar corrupt payments or unreasonable gifts to foreign governments or officials. We believe that our commitment to honesty and integrity, set out in our Guiding Principles and regularly communicated, and the large number of our executives and employees who have served the company for a long time, significantly enhance the likelihood that we will comply with those laws and regulations. More specifically, we have policies and controls in place that are designed to ensure compliance with these laws and regulations, including policies distributed annually to employees, controls and oversight at individual operating companies and companywide, and whistleblower programs that are monitored by senior management and the Board of Directors. Despite these policies and controls, it is possible that an employee or intermediary could fail to comply with applicable laws

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and regulations, which could expose us to civil penalties, criminal penalties and other sanctions, including fines or other punitive actions. In addition, such violations could damage our business and/or reputation and therefore have a material adverse effect on our financial condition and results of operations.

Certain business practices of the insurance industry have been the subject of negative publicity and investigations by government authorities and the subject of class action litigation.

From time to time, the insurance industry has been subject to investigations, litigation and regulatory activity by various insurance, governmental and enforcement authorities, concerning certain practices within the industry. We sometimes receive inquiries and informational requests from insurance regulators or other government officials in the jurisdictions in which our insurance and reinsurance subsidiaries operate. Our internal and external legal counsels coordinate with operating companies in responding to information requests and government proceedings. From time to time, consumer advocacy groups or the media also focus attention on certain insurance industry practices. We cannot predict at this time the effect that investigations, litigation and regulatory activity or negative publicity from consumers or the media will have on the insurance or reinsurance industry or our business, or whether activities or practices currently thought to be lawful will be characterized in the future as unlawful or will become subject to negative scrutiny from consumer advocacy groups or the media. Our involvement in any investigations and related lawsuits would cause us to incur legal costs and, if we were found to have violated any laws, we could be required to pay fines and damages, perhaps in material amounts. In addition, we could be materially adversely affected by the negative publicity for the insurance industry related to any such proceedings, and by any new industry-wide regulations or practices that may result from such proceedings or publicity. It is possible that future investigations or related regulatory developments will mandate changes in industry practices in a fashion that increases our costs of doing business or requires us to alter aspects of the manner in which we conduct our business.

Political and other developments in foreign jurisdictions in which we operate could adversely affect our business and assets.

Our international operations are regulated in various jurisdictions with respect to licensing requirements, currency, amount and type of security deposits, amount and type of reserves, amount and type of local investment and other matters. We regularly monitor for political and other changes in each country where we operate. The decentralized nature of our operations generally permits quick adaptation to, or mitigation of, evolving regional risks. Furthermore, our international operations are widespread and therefore not dependent on the economic stability of any one particular region. International operations and assets held abroad may, however, be adversely affected by political and other developments in foreign countries, including possibilities of tax changes, nationalization and changes in regulatory policy, as well as by consequences of hostilities and unrest. The risks of such occurrences and their overall effect upon us vary from country to country and cannot easily be predicted.

We may be subject to regulatory proceedings or significant litigation, which will be expensive and time consuming and, if decided against us, could require us to pay substantial judgments or settlements.

We may, from time to time, become party to a variety of legal claims and regulatory proceedings, including, but not limited to: disputes over coverage or claims adjudication; disputes regarding sales practices, disclosures, premium refunds, licensing, regulatory compliance and compensation arrangements; disputes with our agents, brokers or network providers over compensation and termination of contracts and related claims; regulatory actions relating to consumer pressure in relation to benefits realized by insurers; disputes with taxing authorities regarding our tax liabilities and tax assets; regulatory proceedings and litigation related to acquisitions or divestitures made or proposed by us or our subsidiaries or in connection with companies in which we hold an investment; and disputes relating to certain businesses acquired or disposed of by us. Operating companies manage day-to-day regulatory and legal risk primarily by implementing appropriate policies, procedures and controls. Internal and external legal counsels also work closely with the operating companies to identify and mitigate areas of potential regulatory and legal risk. The existence of such claims against us or our affiliates, directors or officers could have various adverse effects, including negative publicity and the incurrence of significant legal expenses defending claims, even those without merit.

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Our computer and data processing systems may fail or be perceived to be insecure, which could adversely affect our business and damage our customer relationships.

Our business is highly dependent upon the successful and uninterrupted functioning of our computer and data processing systems. We rely on these systems to perform actuarial and other modeling functions necessary for writing business, to process and make claim payments and to process and summarize investment transactions. We have a highly trained staff that is committed to the continual development and maintenance of these systems. Third parties provide certain of the key components of our business infrastructure such as voice and data communications and network access. Given the high volume of transactions processed daily, we are reliant on such third party provided services to successfully deliver our products and services. We have highly trained information technology staff that is committed to the continual development and maintenance of our technology infrastructure. Security measures, including data security programs to protect confidential personal information, have been implemented and are regularly upgraded. We, together with our third party service providers, also maintains and regularly test contingency plans for our technology infrastructure. Notwithstanding these measures, the failure of these systems could interrupt our operations or materially impact our ability to rapidly evaluate and commit to new business opportunities. If sustained or repeated, a system failure could result in the loss of existing or potential business relationships, or compromise our ability to pay claims in a timely manner.

In addition, a security breach of our computer systems could damage our reputation or result in liability. We retain confidential information regarding our business dealings in our computer systems, including, in some cases, confidential personal information regarding our insureds. We may be required to spend significant capital and other resources to protect against security breaches or to alleviate problems caused by such breaches. Any well-publicized compromise of security could deter people from conducting transactions that involve transmitting confidential information to our systems. Therefore, it is critical that these facilities and infrastructure remain secure and are perceived by the marketplace to be secure. This infrastructure may be vulnerable to physical break-ins, computer viruses, programming errors, attacks by third parties or similar disruptive problems. In addition, we could be subject to liability if hackers were able to penetrate our network security or otherwise misappropriate confidential information.

A disruption of our information technology systems could significantly affect our business.

We rely on information technology in virtually all aspects of our business. A significant disruption or failure of our information technology systems could result in service interruptions, safety failures, security violations, regulatory compliance failures, and inability to protect information and assets against intruders, and other operational difficulties. Attacks perpetrated against our information systems could result in loss of assets and critical information, potential breach of privacy laws, expose us to remediation costs and reputational damage, and adversely affect our results of operations, financial condition and liquidity.

Cyber-attacks could further adversely affect our ability to operate facilities, information technology and business systems, or compromise confidential customer and employee information. Cyber-attacks resulting in political, economic, social or financial market instability or damage to or interference with our operational assets, or our customers or suppliers may result in business interruptions, lost revenue, higher commodity prices, disruption in fuel supplies, lower energy consumption, unstable markets, increased security and repair or other costs, any of which may materially affect our consolidated financial results. Furthermore, instability in the financial markets as a result of terrorism, sustained or significant cyber-attacks, or war could also materially adversely affect our ability to raise capital.

We have taken steps intended to mitigate these risks, including implementation of cyber security and cyber resilience measures, business continuity planning, disaster recovery planning and business impact analysis, and regularly update these plans and security measures, however, there can be no assurance that such steps will be adequate to protect us from the impacts of a cyber-attack.

Our significant shareholder may substantially influence our direction and operations.

Mr. Prem Watsa, our Chairman and Chief Executive Officer, owns, directly or indirectly, or exercises control or direction over shares representing approximately 43.6% of the voting power of our outstanding shares. Mr. Watsa has the ability to substantially influence certain actions requiring shareholder approval,

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including approving a business combination or consolidation, liquidation or sale of our assets, electing members of our board of directors and adopting amendments to our articles of incorporation and by-laws.

Amendments were made to the terms of our multiple voting shares, which are controlled by Mr. Watsa, in August of 2015 having the effect of preserving the voting power represented by the multiple voting shares at 41.8% even if additional subordinate voting shares are issued in the future.

We may be adversely affected by foreign currency fluctuations.

Our reporting currency is the U.S. dollar. A portion of our premiums and our expenses are denominated in foreign currencies and a portion of our assets (including investments) and loss reserves are also denominated in foreign currencies. We may, from time to time, experience losses resulting from fluctuations in the values of foreign currencies (including when our foreign currency assets and liabilities are hedged) which could adversely affect our financial condition, profitability or cash flows.

We rely on independent brokers over whom we exercise little control, which exposes us to certain risks.

We use brokers to distribute our business and in some instances will distribute through agents or directly to customers. We may also conduct business through third parties such as managing general agents where it is cost effective to do so and where we can control the underwriting process to ensure our risk management criteria are met. Each of these channels has its own distinct distribution characteristics and customers. A large majority of our business is generated by brokers (including international reinsurance brokers with respect to the company’s reinsurance operations), with the remainder split among the other distribution channels. This is substantially consistent across our insurance and reinsurance subsidiaries.

Our insurance operations have relationships with many different types of brokers including independent retail brokers, wholesale brokers and national brokers depending on the particular jurisdiction, while our reinsurance operations are dependent primarily on a limited number of international reinsurance brokers. We transact business with these brokers on a non-exclusive basis. These independent brokers also transact the business of our competitors and there can be no assurance as to their continuing commitment to distribute our insurance and reinsurance products. Our continued profitability depends, in part, on the marketing efforts of independent brokers and our ability to offer insurance and reinsurance products and maintain financial ratings that meet the requirements and preferences of such brokers and their policyholders.

Because the majority of our brokers are independent, there is limited ability to exercise control over them. In the event that an independent broker exceeds its authority by binding us on a risk which does not comply with our underwriting guidelines, we may be at risk for that policy until the application is received and a cancellation effected. Although to date we have not experienced a material loss from improper use of binding authority by our brokers, any improper use of such authority may result in losses that could have a material adverse effect on our business, financial condition, profitability or cash flows. Our insurance and reinsurance subsidiaries closely manage and monitor broker relationships and regularly audit broker compliance with our established underwriting guidelines.

To extent that the value of our goodwill, indefinite-lived intangible assets or investments in associates is impaired, we are required to write down the value of such assets.

A portion of our assets are comprised of goodwill, indefinite-lived intangible assets and investments in associates which have arisen principally from various acquisitions and investments made by us or our operating subsidiaries. We test the carrying value of goodwill and indefinite-lived intangible assets for impairment at least annually or more often if events or circumstances indicate there may be an impairment. Investments in associates with carrying values that exceed their fair values are tested for impairment at each reporting date. To the extent we identify that the value of goodwill, indefinite-lived intangible assets or investments in associates is impaired, we are required to write down the value of such assets to their recoverable amount. Continued profitability and achievement of financial plans by our acquired businesses and associates is a key driver for there to be no impairment in the carrying value of our goodwill, indefinite-lived intangible assets and investments in associates. As a result of the COVID-19 pandemic, during 2020, our share of losses of associates was approximately $113 million, which principally reflected non-cash impairment losses related to our investments in Quess, Resolute, Atlas Mara and Astarta of approximately $240 million. We may experience

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additional impairment losses in our investments in the future, and the impact of such losses may be material and adverse to our results of operations.

The goodwill, indefinite-lived intangible assets and investments in associates on our consolidated balance sheet originated from various acquisitions and investments made by us or our operating subsidiaries. Continued profitability and achievement of financial plans by acquired businesses and associates is a key consideration for there to be no impairment in the carrying value of goodwill, indefinite-lived intangible assets and investments in associates. An intangible asset may be impaired if the economic benefit to be derived from its use is unexpectedly diminished. An investment in associate is considered to be impaired if its carrying value exceeds its recoverable amount (the higher of the associate’s fair value and value-in-use).

Management regularly reviews the current and expected profitability of operating companies and associates and their success in achieving financial plans when assessing the carrying value of goodwill, indefinite-lived intangible assets and investments in associates. The carrying values of goodwill and indefinite-lived intangible assets are tested for impairment at least annually or more often if events or circumstances indicate there may be impairment. Investments in associates with carrying values that exceed their fair values are tested for impairment using value-in-use discounted cash flow models at each reporting date.

Our failure to realize deferred income tax assets could lead to a writedown or tax authorities may take differing positions from ours, either of which could adversely affect our results of operations.

Realization of deferred income tax assets is dependent upon the generation of taxable income in those jurisdictions where the relevant tax losses and temporary differences exist. Failure to achieve projected levels of profitability could lead to a reduction in our deferred income tax asset if it is no longer probable that the amount of the asset will be realized.

We are subject to income taxes in Canada, the United States and many foreign jurisdictions where we operate, and our determination of our tax liability is subject to review by applicable domestic and foreign tax authorities. We also consult with external tax professionals as needed. Tax legislation of each jurisdiction in which we operate is interpreted to determine the provision for income taxes and expected timing of the reversal of deferred income tax assets and liabilities. While we believe our tax positions to be reasonable, where our interpretations differ from those of tax authorities or the timing of realization is not as expected, the provision for income taxes may increase or decrease in future periods to reflect actual experience.

Technological or other changes could adversely impact demand, or the premiums payable, for the insurance coverages we offer.

Technological changes could have unpredictable effects on the insurance and reinsurance industries. It is expected that new services and technologies will continue to emerge that will affect the demand for insurance and reinsurance products and services, the premiums payable, the profitability of such products and services and the risks associated with underwriting certain lines of business, including new lines of business. While we strive to maintain an innovation working group comprised of members with diverse backgrounds from across our global operating companies to regularly assess new services and technologies that may be applicable or disruptive to the insurance and reinsurance industries, failure to understand evolving technologies, or to position us in the appropriate direction, or to deploy new products and services in a timely way that considers customer demand and competitor activities could have an adverse impact on our business, financial condition, profitability or cash flows.

Assessments and other surcharges for guaranty funds and second-injury funds and other mandatory pooling arrangements may reduce the profitability of our insurance subsidiaries.

Virtually all U.S. states require insurers licensed to do business in their state to bear a portion of the loss suffered by some insureds as a result of impaired or insolvent insurance companies. Many states also have laws that establish second-injury funds to provide compensation to injured employees for aggravation of a prior condition or injury. In addition, as a condition to the ability to conduct business in various jurisdictions, some of our insurance subsidiaries are required to participate in mandatory property and casualty shared market mechanisms or pooling arrangements, which provide various types of insurance coverage to individuals or other entities that otherwise are unable to purchase that coverage from private insurers. The effect of these

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assessments and mandatory shared-market mechanisms or changes in them could reduce the profitability of our U.S. insurance subsidiaries in any given period or limit their ability to grow their business. Similarly, our Canadian insurance subsidiaries contribute to mandatory guaranty funds that protect insureds in the event of a Canadian property and casualty insurer becoming insolvent, and certain of our Asian insurance subsidiaries participate in mandatory pooling arrangements in their local markets.

Risk Factors Relating to the Exchange Notes

The market value of the Exchange Notes may be affected by changes in credit ratings.

The value of the Exchange Notes will be affected by the general creditworthiness of the Company. Real or anticipated changes in credit ratings on the Exchange Notes may affect the market value of the Exchange Notes. No assurance can be given that any credit rating assigned to the Exchange Notes will not be lowered or withdrawn entirely by the relevant rating agency or that negative trends will not be applied by any ratings agency.

The Initial Notes were assigned a rating of BBB(H) by DBRS Morningstar (“DBRS”), Baa3 by Moody’s Investor Service, Inc. (“Moody’s”) and BBB by Standard and Poor’s Ratings Services, a division of S&P Global, Inc. (“S&P”). One or more other independent credit rating agencies may assign credit ratings to the Exchange Notes. The ratings may not reflect the potential impact of all risks related to the structure, market, additional risk factors discussed herein and other factors that may affect the value of the Exchange Notes. A credit rating is not a recommendation to buy, sell or hold securities and may be subject to revision, suspension or withdrawal by the rating agency at any time. No assurance can be given that a credit rating will remain constant for any given period of time or that a credit rating will not be lowered or withdrawn entirely by the credit rating agency if, in its judgment, circumstances in the future so warrant. A suspension, reduction or withdrawal at any time of a credit rating assigned to the Exchange Notes by one or more of the credit rating agencies may adversely affect the cost and terms and conditions of our financing and could adversely affect the value and trading of the Exchange Notes.

The Exchange Notes are effectively subordinated to the indebtedness of our subsidiaries.

The Exchange Notes are effectively subordinated to any existing and future indebtedness and other liabilities of our subsidiaries. You will not have any claim as a creditor against our subsidiaries or the assets of our subsidiaries. Therefore, in the event of the insolvency or liquidation of a subsidiary, following payment by such subsidiary of its liabilities, the subsidiary may not have sufficient remaining assets to make payments to us as a shareholder or otherwise. In the event of a default by a subsidiary under any credit agreement or other indebtedness, its creditors could accelerate the debt, prior to such subsidiary distributing amounts to us that we could use to make payments on the Exchange Notes. In addition, if we caused a subsidiary to pay a dividend to us to make payments on the Exchange Notes, and the dividend was determined to be improperly paid, holders of the Exchange Notes would be required to return the payment to the subsidiary’s creditors.

As of June 30, 2021, our subsidiaries had $2.7 billion principal amount of indebtedness, of which $1.8 billion principal amount of indebtedness is held by our non-insurance subsidiaries and is non-recourse to Fairfax. Our subsidiary debt may increase in the future. The terms of the Exchange Notes do not limit the ability of our subsidiaries to incur additional indebtedness that is senior to the Exchange Notes.

We may incur additional indebtedness that may adversely affect our ability to meet our financial obligations under the Exchange Notes.

Our obligations under the Exchange Notes rank equally with all of our other unsecured senior indebtedness. As of June 30, 2021, the Company had approximately $6.2 billion principal amount of total outstanding indebtedness, including $500.0 million drawn under our Credit Facility. In addition, subsequent to June 30, 2021 and up to the date hereof, we have fully repaid our Credit Facility. The indenture governing the Exchange Notes does not limit the amount of additional indebtedness that we may incur. We may incur additional indebtedness in the future, which could have important consequences to holders of the Exchange Notes, including the following:

•

we could have insufficient cash to meet our financial obligations, including our obligations under the Exchange Notes;

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•

our ability to obtain additional financing for working capital, capital expenditures or general corporate purposes may be impaired; and

•

a significant degree of debt could make us more vulnerable to changes in general economic conditions and could also affect the financial strength ratings of our insurance and reinsurance subsidiaries.

Holders of the Exchange Notes may not be protected in the event we are involved in a highly leveraged transaction, reorganization, restructuring, merger or similar transaction in the future.

The Indenture under which the Initial Notes were issued may not sufficiently protect holders of the Exchange Notes if we are involved in a highly leveraged transaction, reorganization, restructuring, merger or similar transaction. The Indenture does not contain:

•

any provision restricting us or any of our subsidiaries from incurring, assuming or being liable with respect to any indebtedness or other obligations;

•

any provision restricting us or our subsidiaries from incurring, assuming or being liable with respect to any unsecured indebtedness or other unsecured obligations;

•

any provision restricting us or any of our subsidiaries from paying dividends or making other distributions on capital stock or from purchasing or redeeming capital stock;

•

any restrictions on the ability of our subsidiaries to issue securities that would be senior to the common shares of the subsidiary held by us;

•

any financial ratios or specified level of net worth to which we or our subsidiaries must adhere; or

•

any specific restrictions on our ability to contribute our assets to our insurance subsidiaries.

The price at which you may be able to resell your Exchange Notes may be adversely affected by factors that are beyond our control.

If you are able to resell your Exchange Notes, the price you receive will depend on many factors that may vary over time, including:

•

the number of potential buyers;

•

the level of liquidity of the Exchange Notes;

•

our financial performance;

•

the amount of indebtedness we have outstanding;

•

the level, direction and volatility of market interest rates generally; and

•

the market for similar securities.

Prevailing yields on similar securities will affect the market value of the Exchange Notes. Assuming all other factors remain unchanged, the market value of the Exchange Notes would be expected to decline as prevailing yields for similar securities rise and would be expected to increase as prevailing yields for similar securities decline. Spreads over the U.S. treasury yields and comparable benchmark rates of interest for similar securities will also affect the market value of the Exchange Notes in an analogous manner.

As a result of these factors, you may only be able to sell your Exchange Notes at prices below those you believe to be appropriate, including prices below the price at which you acquired the Initial Notes.

There may be no active market for the Exchange Notes.

There is currently no public market for the Exchange Notes, and we do not intend to apply for listing of the Exchange Notes on any securities exchange or any automated quotation system. Accordingly, we cannot be sure that any active market for the Exchange Notes will develop, or if one does develop, that it will be maintained. If an active market for the Exchange Notes fails to develop or be sustained, the trading price of the Exchange Notes could decline.

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The Exchange Notes may be redeemed prior to maturity.

The Exchange Notes may be redeemed, at our option, in whole at any time or in part from time to time on or after the closing of the Exchange Offer and prior to the maturity date, or in whole but not in part in the event of certain developments affecting Canadian taxation. Holders of Exchange Notes should assume that our redemption option will be exercised if it is in our interest to redeem the Exchange Notes. Holders whose Exchange Notes are redeemed would not be entitled to participate in any future growth in the market price of the Exchange Notes and may not be able to reinvest their redemption proceeds in securities providing a comparable expected rate of return to maturity as the Exchange Notes for a comparable level of risk. See “Description of the Notes — Optional Redemption” and “Description of the Notes — Redemption for Tax Reasons”.

Risk Factors Relating to the Exchange Offer

If you do not validly tender your Initial Notes, you will not receive Exchange Notes in the Exchange Offer, and the resale restrictions applicable to the Initial Notes will continue to apply to those Initial Notes that are not validly exchanged.

Only Initial Notes that are validly tendered (and not validly withdrawn) will be exchanged in the Exchange Offer and registered under the Securities Act. The Initial Notes that are not so exchanged will continue to be subject to restrictions on transfer under applicable U.S. federal and state securities laws, and while subject to such restrictions, may not be offered, sold or transferred in the United States except pursuant to an exemption from the registration requirements of, or in a transaction not subject to, the Securities Act and applicable state securities laws, or pursuant to an effective registration statement. Upon consummation of the Exchange Offer, certain registration and other rights under the Registration Rights Agreement will terminate. The Company will issue Exchange Notes only in exchange for Initial Notes that are timely received by the exchange agent, together with all required documents, including a properly completed and duly signed letter of transmittal or notice of guaranteed delivery. Therefore, you should allow sufficient time to ensure timely delivery of the Initial Notes and should carefully follow the instructions on how to tender your Initial Notes.

Neither the Company nor the exchange agent is required to notify you of any defects or irregularities with respect to your tender of the Initial Notes. If you do not tender your Initial Notes or if the Company does not accept your Initial Notes because you did not tender your Initial Notes properly, then, after consummation of the Exchange Offer, you will continue to hold Initial Notes that are subject to existing transfer restrictions.

Although the Company may in the future seek to acquire unexchanged Initial Notes in open market or privately negotiated transactions, through subsequent exchange offers or otherwise, the Company has no present plans to acquire any unexchanged Initial Notes or to file with the SEC a shelf registration statement or a prospectus with any securities regulatory authority in Canada to permit resales of any unexchanged Initial Notes. In addition, holders who do not tender their Initial Notes (except for the initial purchaser or holders of Initial Notes (i) who are prohibited by applicable law or SEC policy from participating in the Exchange Offer, (ii) who may not resell the Exchange Notes acquired in the Exchange Offer without delivering a prospectus or (iii) for whom this short form prospectus is not appropriate or available for resales of Exchange Notes acquired in the Exchange Offer) will not have any further registration rights and will not have the right to receive additional interest on their Initial Notes.

The market for the Initial Notes may be significantly more limited after the Exchange Offer.

Because we anticipate that most holders of Initial Notes will elect to exchange their Initial Notes, it is likely that the liquidity of the market for any Initial Notes remaining after the completion of the Exchange Offer may be substantially limited. Any Initial Notes tendered and exchanged in the Exchange Offer will reduce the aggregate principal amount of the Initial Notes outstanding. Accordingly, the liquidity of the market for any remaining Initial Notes could be adversely affected and you may be unable to sell them. The extent of the market for the Initial Notes and the availability of price quotations would depend on a number of factors, including the number of holders of Initial Notes remaining outstanding and the interest of securities firms in maintaining a market in the Initial Notes. An issue of securities with a smaller number of units available for trading may command a lower, and more volatile, price than would a comparable issue of securities with a larger number of units available for trading; therefore, the market price for the Initial Notes

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that are not exchanged may be lower and more volatile as a result of the reduction in the aggregate principal amount of the Initial Notes outstanding.

If you do not properly tender your Initial Notes, you will not receive Exchange Notes in the Exchange Offer, and you may not be able to sell your Initial Notes.

Some persons who participate in the Exchange Offer must deliver a prospectus in connection with resales of the Exchange Notes.

If you exchange your Initial Notes in the Exchange Offer for the purpose of participating in a distribution of the Exchange Notes, you may be deemed to have received restricted securities and, if so, will be required to comply with the registration and prospectus delivery requirements of the Securities Act in connection with any resale transaction.

Based on our understanding of interpretations of the Staff of the SEC set forth in no-action letters issued to third parties, including Exxon Capital Holdings Corporation (available May 13, 1988), Morgan Stanley & Co. Incorporated (available June 5, 1991) and Shearman & Sterling (available July 2, 1993), we believe that holders who (i) are not “affiliates” of the Company within the meaning of Rule 405 under the Securities Act; (ii) acquire their Exchange Notes in the ordinary course of business; (iii) do not engage in, intend to engage in, or have arrangements to participate in a distribution (within the meaning of the Securities Act) of the Exchange Notes; and (iv) are not broker-dealers, may offer for resale, resell or otherwise transfer the Exchange Notes without compliance with the registration and prospectus delivery requirements of the Securities Act. Holders described in the preceding sentence must tell us in writing at our request that they meet these criteria.

Holders that do not meet these criteria could not rely on interpretations of the SEC in no-action letters, and will have to register the Exchange Notes they receive in the Exchange Offer and deliver a prospectus for them. If such a holder transfers any Exchange Notes without delivering a prospectus meeting the requirements of the Securities Act or without an applicable exemption from registration under the Securities Act, such a holder may incur liability under the Securities Act. We do not and will not assume, or indemnify such a holder against, this liability. In addition, holders that are broker-dealers may be deemed “underwriters” within the meaning of the Securities Act in connection with any resale of Exchange Notes in the United States acquired in the Exchange Offer. Holders that are broker-dealers that receive Exchange Notes for their own account in exchange for Initial Notes that were acquired as a result of market-making activities or other trading activities must acknowledge that they will deliver a prospectus (or, to the extent permitted by law, make available a prospectus to purchasers) in connection with any resale of Exchange Notes in the United States they acquire in the Exchange Offer in order not to be deemed an underwriter.

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USE OF PROCEEDS

The Company will not receive any cash proceeds from the issuance of the Exchange Notes. The Company is making this exchange solely to satisfy its obligations under the Registration Rights Agreement entered into in connection with the offering of the Initial Notes. In consideration for issuing the Exchange Notes, the Company will receive Initial Notes in the same aggregate principal amount. The Company has agreed to pay the expenses of the Exchange Offer, other than certain taxes. The form and terms of the Exchange Notes are identical in all material respects to the form and terms of the Initial Notes, except as otherwise described herein, including under “The Exchange Offer — Terms of the Exchange Offer”. The Initial Notes surrendered in exchange for the Exchange Notes will be retired and cancelled and will not be reissued. Accordingly, the issuance of the Exchange Notes will not result in any change in our outstanding indebtedness.

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CONSOLIDATED CAPITALIZATION

The table below sets forth our holding company cash and investments and capitalization as of June 30, 2021 on an actual basis and as adjusted to give effect to certain other transactions of the Company after June 30, 2021, as indicated in the footnotes to the table below. You should read this table in conjunction with our unaudited interim consolidated financial statements as of and for the three and six months ended June 30, 2021, incorporated by reference in this short form prospectus. As no proceeds will be realized from the Exchange Offer, the completion of the Exchange Offer will have no material change on our capitalization.

	As of June 30, 2021
(in millions of U.S. dollars)	Actual			As Adjusted
Holding company cash and investments (net of derivative obligations)(1)		$	1,413.4		$	1,707.0
Debt(2)
Borrowings – holding company(3)		$	6,130.7		$	5,500.5
Borrowings – insurance and reinsurance companies			851.5			851.5
Borrowings – non-insurance companies			1,834.8			1,834.8
Total debt			8,817.0			8,186.8
Net debt			7,403.6			6,479.8
Equity
Common shareholders’ equity(4)			14,015.1			14,142.7
Preferred equity			1,335.5			1,335.5
Non-controlling interests(5)			4,186.2			4,669.1
Total equity			19,536.8			20,147.3
Total capitalization		$	28,353.8		$	28,334.1
Total debt as a percentage of total capitalization			31.1%			28.9%
Net debt as a percentage of net total capitalization(6)			27.5%			24.3%

(1)

The “As Adjusted” holding company cash and investments (net of derivative obligations) principally reflects (1) the repayment of $500.0 million on the Credit Facility, (2) proceeds of approximately $375 million from the sale of an approximate 14% interest in Brit to OMERS, (3) proceeds of approximately $700 million from the sale of our 60.0% interest in Riverstone Barbados, (4) payment of approximately $143 million for an additional 30.0% interest in Eurolife, and (5) purchases of $21.0 million of our Subordinate Voting Shares for use in our share-based payment awards during the period from July 1, 2021 to September 8, 2021.

(2)

See note 15 to our audited consolidated financial statements as of and for the year ended December 31, 2020 and note 10 to our unaudited interim consolidated financial statements as of and for the three and six months ended June 30, 2021, incorporated by reference in this short form prospectus, for details of our borrowings and credit facilities.

(3)

The “As Adjusted” borrowings — holding company principally reflects the repayment of $500.0 million on the Credit Facility.

(4)

The “As Adjusted” common shareholders’ equity reflects (1) the sale of an approximate 14% interest in Brit to OMERS, (2) the sale of our 60.0% joint venture interest in Riverstone Barbados, (3) the consolidation of the net assets of Eurolife, and (4) purchases of $21.0 million of our Subordinate Voting Shares for use in our share-based payment awards during the period from July 1, 2021 to September 8, 2021.

(5)

Primarily includes non-controlling interests in Allied World, Fairfax India, Recipe, Dexterra Group, Thomas Cook India and Brit. The “As Adjusted” non-controlling interests reflects (1) the sale of an approximate 14% interest in Brit to OMERS, and (2) the consolidation of Eurolife.

(6)

Net debt is calculated by the Company as total debt less holding company cash and investments (net of derivative obligations). Net total capitalization is calculated by the Company as the sum of total equity and net debt.

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EARNINGS COVERAGE RATIOS

The following consolidated financial ratios are calculated for the twelve-month periods ended June 30, 2021 and December 31, 2020.

The “As Adjusted” ratio for the twelve months ended June 30, 2021 gives effect as of July 1, 2020 to:

repayment of $500.0 million under the Credit Facility; and

ii.

the Exchange Offer.

The “As Adjusted” ratio for the twelve months ended December 31, 2020 gives effect as of January 1, 2020 to:

the Company’s issuance on March 3, 2021 of $600.0 million principal amount of 3.375% unsecured senior notes due March 3, 2031 (the Initial Notes);

ii.

the Company’s issuance on March 1, 2021 of Cdn$850 aggregate principal amount of 3.95% unsecured senior notes due March 3, 2031, the proceeds of which were used for early redemption on March 29, 2021 of our Cdn$446.0 million principal amount of 5.84% unsecured senior notes due October 14, 2022 and Cdn$400.0 million principal amount of 4.50% unsecured senior notes due March 22, 2023, inclusive of a loss of $45.7 million on redemption;

iii.

repayment of $700.0 million under the Credit Facility; and

iv.

the Exchange Offer.

Except as described above, the following table does not reflect the interest cost of our debt and the debt of our subsidiaries or the preferred share dividend requirements on preferred shares issued during the periods as if they were issued at the beginning of the periods.

Twelve Months Ended

June 30, 2021

December 31, 2020

Actual

As Adjusted

Actual

As Adjusted

Earnings coverage(1)

8.3

8.5

1.4

1.3

(1)

Earnings coverage is equal to consolidated net earnings before interest expense on borrowings and income taxes divided by consolidated interest expense on borrowings and preferred share dividend distributions adjusted to a before tax equivalent at the Company’s statutory income tax rate of 26.5%.

Our consolidated interest expense on borrowings amounted to $459.4 million and $413.1 million for the twelve-month periods ended June 30, 2021 and December 31, 2020, respectively. Our preferred share dividend requirements, adjusted to a before tax equivalent at the Company’s statutory income tax rates, amounted to $60.7 million and $59.9 million for the twelve-month periods ended June 30, 2021 and December 31, 2020, respectively. Our consolidated net earnings before interest expense on borrowings and income taxes for the twelve-month periods ended June 30, 2021 and December 31, 2020 were $4.3 billion and $657.2 million, respectively, which was 8.3 and 1.4 times our consolidated interest expense on borrowings and preferred share dividend requirements for the twelve-month periods ended June 30, 2021 and December 31, 2020, respectively.

After giving effect to the adjustments as described above as of the beginning of the periods, our consolidated interest expense on borrowings would have amounted to $449.4 million and $457.3 million for the twelve-month periods ended June 30, 2021 and December 31, 2020, respectively.

After giving effect to the adjustments as described above as of the beginning of the periods, our consolidated net earnings (loss) before interest expense on borrowings and income taxes for the twelve-month periods ended June 30, 2021 and December 31, 2020 would have been $4.3 billion and $657.2 million, respectively, which was 8.5 and 1.3 times our consolidated interest expense on borrowings and preferred share dividend requirements for the twelve-month periods ended June 30, 2021 and December 31, 2020, respectively.

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DESCRIPTION OF MATERIAL INDEBTEDNESS AND OTHER COMMITMENTS

Exchange Notes and Initial Notes

On March 3, 2021, the Company issued $600.0 million aggregate principal amount of its 3.375% Senior Notes due 2031, or the Initial Notes, under the Indenture. If all the conditions of the Exchange Offer are satisfied, the Company intends to exchange the Initial Notes that are validly tendered and not validly withdrawn for an equal principal amount of Exchange Notes.

Other Indebtedness

As of June 30, 2021, we had $8.9 billion principal amount of total outstanding indebtedness (including the Initial Notes and indebtedness under the Credit Facility). Subsequent to June 30, 2021, we repaid the full $500.0 million outstanding on the Credit Facility. We had $8.8 billion principal amount of total outstanding indebtedness as of December 31, 2020.

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THE EXCHANGE OFFER

Terms of the Exchange Offer

General

In connection with the issuance of the Initial Notes, the Company entered into the Registration Rights Agreement with the initial purchasers of the Initial Notes. The following contains a summary of the provisions of the Registration Rights Agreement. Because this is a summary description, it does not contain all of the information that may be important to an investor in the Exchange Notes and is qualified in its entirety by the Registration Rights Agreement. We refer you to the Registration Rights Agreement, which has been filed as an exhibit to the registration statement of which this short form prospectus forms a part.

Under the Registration Rights Agreement, the Company agreed to file under the Securities Act and use its commercially reasonable efforts to cause to become effective under the Securities Act, on or prior to 360 days after the closing of the offering of the Initial Notes, the registration statement of which this short form prospectus is a part with respect to a registered offer to exchange the Initial Notes for Exchange Notes. The Company is required to keep the Exchange Offer open for at least 20 business days (or longer if required by law) after the date notice of the Exchange Offer is mailed to holders of the Initial Notes. If the Company fails to comply with certain obligations under the Registration Rights Agreement, we will be required to pay additional interest to holders of the Initial Notes.

Upon the terms and subject to the conditions set forth in the registration statement filed on Form F-10 with the SEC, which includes this short form prospectus, and in the letter of transmittal, all Initial Notes validly tendered and not validly withdrawn prior to the Expiration Date will be accepted for exchange. Exchange Notes will be issued in exchange for an equal principal amount of outstanding Initial Notes accepted in the Exchange Offer. This short form prospectus, together with the letter of transmittal, is being sent to all holders of Initial Notes as of the date of this short form prospectus. The Exchange Offer is not conditioned upon any minimum principal amount of Initial Notes being tendered for exchange. However, the obligation to accept Initial Notes for exchange pursuant to the Exchange Offer is subject to certain customary conditions as set forth herein under “— Conditions”.

Initial Notes shall be deemed to have been accepted as validly tendered when, as and if the Company has given written notice thereof to The Bank of New York Mellon, the exchange agent. The exchange agent will act as agent for the tendering holders of Initial Notes for the purposes of receiving the Initial Notes and delivering Exchange Notes to such holders.

Based on the Company’s understanding of interpretations of the Securities Act by the staff of the SEC set forth in several no-action letters to third parties, including Exxon Capital Holdings Corporation (available May 13, 1988), Morgan Stanley & Co. Incorporated (available June 5, 1991) and Shearman & Sterling (available July 2, 1993), the Company believes that holders who (i) are not “affiliates” of the Company within the meaning of Rule 405 under the Securities Act, (ii) acquire their Exchange Notes in the ordinary course of business, (iii) do not engage in, intend to engage in, or have arrangements to participate in a distribution (within the meaning of the Securities Act) of the Exchange Notes, and (iv) are not broker-dealers, may offer for resale, resell or otherwise transfer the Exchange Notes without compliance with the registration and prospectus delivery requirements of the Securities Act. Holders described in the preceding sentence must tell the Company in writing at the Company’s request that they meet these criteria.

By tendering Initial Notes in exchange for Exchange Notes and executing the letter of transmittal, each holder will represent to the Company that:

•

it is neither an affiliate of the Company nor a broker/dealer tendering Initial Notes acquired directly from the Company for its own account;

•

any Exchange Notes to be received by it will be acquired in the ordinary course of its business;

•

at the time of commencement of the Exchange Offer, it is not engaged in, and does not intend to engage in, and has no arrangement or understanding with any person to participate in the distribution (within the meaning of the Securities Act) of the Exchange Notes to be issued in the Exchange Offer; and

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•

it is not acting on behalf of any person who could not truthfully make the foregoing representations.

If such holder is a broker-dealer, it will also be required to represent that the Initial Notes were acquired as a result of market-making activities or other trading activities and that it will deliver a prospectus in connection with any resale of Exchange Notes in the United States. Each holder, whether or not it is a broker-dealer, shall also represent that it is not acting on behalf of any person that could not truthfully make any of the foregoing representations contained in this paragraph. If a holder of Initial Notes is unable to make the foregoing representations, such holder may not rely on the applicable interpretations of the Staff of the SEC and must comply with the registration and prospectus delivery requirements of the Securities Act in connection with any secondary resale transaction in the United States unless such sale is made pursuant to an exemption from such requirements.

Each broker-dealer that receives Exchange Notes for its own account in exchange for Initial Notes where such Initial Notes were acquired by such broker-dealer as a result of market-making or other trading activities, must acknowledge that it will deliver a prospectus meeting the requirements of the Securities Act and that it has not entered into any arrangement or understanding with the Company or an affiliate of the Company to distribute the Exchange Notes in connection with any resale of such Exchange Notes.

We have not entered into any arrangement or understanding with any person who will receive Exchange Notes in the Exchange Offer to distribute such Exchange Notes following completion of the Exchange Offer. We are not aware of any person that will participate in the Exchange Offer with a view to distribute the Exchange Notes.

Upon consummation of the Exchange Offer, any Initial Notes not tendered will remain outstanding and continue to accrue interest but, subject to certain limited exceptions, holders of Initial Notes who do not exchange their Initial Notes for Exchange Notes in the Exchange Offer will no longer be entitled to registration rights or the payment of additional interest. In addition, such holders will not be able to offer or sell their Initial Notes, unless such Initial Notes are subsequently registered under the Securities Act, except pursuant to an exemption from, or in a transaction not subject to, the Securities Act and applicable state securities laws. Subject to limited exceptions, the Company will have no obligation to effect a subsequent registration of the Initial Notes.

Expiration Date; Extensions; Amendments; Termination

The Expiration Date shall be 5:00 p.m., New York City time, on , 2021, unless the Company, in its sole discretion, extends the Exchange Offer, in which case the Expiration Date shall be 5:00 p.m., New York City time, on the date to which the Exchange Offer is extended.

To extend the Expiration Date, the Company will notify the exchange agent of any extension by written notice and will notify the holders of Initial Notes by means of a press release or other public announcement prior to 9:00 a.m., New York City time, on the next business day after the Expiration Date. Such announcement will state that the Company is extending the Exchange Offer for a specified period of time.

The Company reserves the right:

•

to delay acceptance of any Initial Notes, to extend the Exchange Offer or to terminate the Exchange Offer and not permit acceptance of Initial Notes not previously accepted if any of the conditions set forth under “— Conditions” shall have occurred and shall not have been waived prior to the Expiration Date, by giving written notice of such delay, extension or termination to the exchange agent; or

•

to amend the terms of the Exchange Offer in any manner deemed by the Company to be advantageous to the holders of the Initial Notes.

Any such delay in acceptance, extension, termination or amendment will be followed as promptly as practicable by written notice to the exchange agent. If the Exchange Offer is amended in a manner determined by the Company to constitute a material change, the Company will promptly disclose such amendment in a manner reasonably calculated to inform the holders of the Initial Notes of such amendment and the Company will extend the Exchange Offer for a period of five to ten business days. In addition, if the Company amends or terminates the Exchange Offer, the Company will promptly file a post-effective amendment to the

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registration statement of which this short form prospectus forms a part. Without limiting the manner in which the Company may choose to make public the announcement of any delay, extension, amendment or termination of the Exchange Offer, the Company shall have no obligation to publish, advertise or otherwise communicate any such public announcement, other than by making a timely release to an appropriate news agency.

Absence of Dissenter’s Rights of Appraisal

Holders of the Initial Notes do not have any dissenter’s rights of appraisal in connection with the Exchange Offer.

Procedures for Tendering

To tender in the Exchange Offer, a holder must do either of the following:

•

properly complete, sign and date the letter of transmittal, including all other documents required by the letter of transmittal; have the signature on the letter of transmittal guaranteed if the letter of transmittal so requires; and deliver that letter of transmittal and other required documents to the exchange agent at the address listed in the letter of transmittal on or before the Expiration Date; or

•

if the Initial Notes are tendered under the book-entry transfer procedures described below, transmit to the exchange agent, on or before the Expiration Date, an agent’s message.

In addition, one of the following must occur:

•

the exchange agent must receive certificates representing the holder’s Initial Notes along with the letter of transmittal on or before the Expiration Date;

•

the exchange agent must receive a timely confirmation of book-entry transfer of the Initial Notes into the exchange agent’s account at The Depository Trust Company (“DTC”), under the procedure for book-entry transfers described below along with the letter of transmittal or a properly transmitted agent’s message, on or before the Expiration Date; or

•

the holder must comply with the guaranteed delivery procedures described below.

The method of delivery of Initial Notes, letter of transmittal and all other required documents is at the election and risk of the holders. If such delivery is by mail, it is recommended that registered mail, properly insured, with return receipt requested, be used. In all cases, sufficient time should be allowed to assure timely delivery. No Initial Notes, letters of transmittal or other required documents should be sent to the Company. Delivery of all Initial Notes, if applicable, letters of transmittal and other documents must be made to the exchange agent before the expiration date at its address set forth in the letter of transmittal. Holders may also request their respective brokers, dealers, commercial banks, trust companies or nominees to effect such tender for such holders.

The tender by a holder of Initial Notes will constitute an agreement between such holder and the Company in accordance with the terms and subject to the conditions set forth herein and in the applicable letter of transmittal. Any beneficial owner whose Initial Notes are registered in the name of a broker, dealer, commercial bank, trust company or other nominee and who wishes to tender should contact such registered holder promptly and instruct such registered holder to tender on its behalf.

Signatures on a letter of transmittal or a notice of withdrawal, as the case may be, must be guaranteed by any member firm of a registered national securities exchange or of the Financial Industry Regulatory Authority, Inc., a commercial bank or trust company having an office or correspondent in the United States or an “eligible guarantor” institution within the meaning of Rule 17Ad-15 under the Exchange Act or an eligible institution unless the Initial Notes tendered pursuant thereto are tendered (1) by a registered holder of Initial Notes who has not completed the box entitled “Special Issuance Instructions” or “Special Delivery Instructions” on the letter of transmittal, or (2) for the account of an eligible institution.

If a letter of transmittal is signed by trustees, executors, administrators, guardians, attorneys-in-fact, officers of corporations or others acting in a fiduciary or representative capacity, such person should so

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indicate when signing and, unless waived by the Company, evidence satisfactory to the Company of their authority to so act must be submitted with such letter of transmittal.

All questions as to the validity, form, eligibility, time of receipt and withdrawal of the tendered Initial Notes will be determined by the Company in its sole discretion, which determination will be final and binding. The Company reserves the absolute right to reject any and all Initial Notes not validly tendered or exchange any Initial Notes if such exchange, in the opinion of counsel for the Company, be unlawful. The Company also reserves the absolute right to waive any irregularities or conditions of tender as to particular Initial Notes. The Company will not waive any condition of the Exchange Offer with respect to an individual holder unless the Company waives that condition for all holders. The Company’s interpretation of the terms and conditions of the Exchange Offer, including the instructions in the letter of transmittal, will be final and binding on all parties. Unless waived, any defects or irregularities in connection with tenders of Initial Notes must be cured within such time as the Company shall determine. Neither the Company, the exchange agent nor any other person shall be under any duty to give notification of defects or irregularities with respect to tenders of Initial Notes, nor shall any of them incur any liability for failure to give such notification. Tenders of Initial Notes will not be, or be deemed to have been, made until all irregularities have been cured or waived. Any Initial Note received by the exchange agent that is not validly tendered and as to which the defects or irregularities have not been cured or waived will be returned without cost to such holder by the exchange agent, unless otherwise provided in the letter of transmittal, promptly following the Expiration Date.

In addition, the Company reserves the right, in its sole discretion, subject to the provisions of the Indenture pursuant to which the Initial Notes were issued:

•

to purchase or make offers for any Initial Notes that remain outstanding subsequent to the Expiration Date or, as described under “— Conditions”, to terminate the Exchange Offer;

•

to redeem Initial Notes as a whole, or in part, at any time and from time to time; and

•

to the extent permitted under applicable law, to purchase Initial Notes in the open market, in privately negotiated transactions or otherwise.

The terms of any such purchases or offers could differ from the terms of the Exchange Offer.

Each broker-dealer that receives Exchange Notes for its own account in exchange for Initial Notes where such Initial Notes were acquired by such broker-dealer as a result of market-making or other trading activities, must acknowledge that it will deliver a prospectus meeting the requirements of the Securities Act and that it has not entered into any arrangement or understanding with the Company, or an affiliate of the Company, to distribute the Exchange Notes in connection with any resale of such Exchange Notes.

Acceptance of Initial Notes for Exchange; Delivery of Exchange Notes

Upon satisfaction or waiver of all of the conditions to the Exchange Offer, all Initial Notes validly tendered will be accepted promptly after the Expiration Date and the Exchange Notes will be issued promptly after acceptance of the Initial Notes. See “— Conditions”. For purposes of the Exchange Offer, Initial Notes shall be deemed to have been accepted as validly tendered for exchange when, as and if the Company has given written notice thereof to the exchange agent.

For each Initial Note accepted for exchange, the holder of such Initial Note will receive an Exchange Note having a principal amount equal to that of the surrendered Initial Note.

In all cases, issuance of Exchange Notes for Initial Notes that are accepted for exchange pursuant to the Exchange Offer will be made only after timely receipt by the exchange agent of:

•

certificates representing the Initial Notes or a timely book-entry confirmation of such Initial Notes into the exchange agent’s account at DTC; and

•

a properly completed and duly executed letter of transmittal and all other required documents or a properly completed agent’s message.

If any tendered Initial Notes are not accepted for any reason described in the terms and conditions of the Exchange Offer, such unaccepted or such non-exchanged Initial Notes will be returned promptly without

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expense to the tendering holder thereof (if in certificated form), or credited to an account maintained with DTC after the expiration or termination of the Exchange Offer.

Book-Entry Transfer

The exchange agent has established an account with respect to the Initial Notes at DTC for purposes of the Exchange Offer. Any financial institution that is a participant in DTC’s systems may make book-entry delivery of Initial Notes by causing DTC to transfer such Initial Notes into the exchange agent’s account at DTC in accordance with DTC’s procedures for transfer. However, although delivery of Initial Notes may be effected through book-entry transfer at DTC, the exchange agent must receive a properly completed and duly executed letter of transmittal with any required signature guarantees and all other required documents at its address listed in the letter of transmittal, or an agent’s message instead of a letter of transmittal, on or before the Expiration Date, or if the holder complies with the guaranteed delivery procedures described below within the time period provided under those procedures.

Exchanging Book-Entry Notes

DTC has confirmed that any financial institution that is a participant in DTC may utilize DTC’s Automated Tender Offer Program (“ATOP”) procedures to tender Initial Notes.

Any participant in DTC may make book-entry delivery of Initial Notes by causing DTC to transfer such Initial Notes into the exchange agent’s account in accordance with DTC’s ATOP procedures for transfer. However, the exchange for the Initial Notes so tendered will only be made after a book-entry confirmation of the book-entry transfer of Initial Notes into the exchange agent’s account and timely receipt by the exchange agent of an agent’s message and any other documents required by the letter of transmittal. The term “agent’s message” means a message, transmitted by DTC and received by the exchange agent and forming part of a book-entry confirmation, which states that DTC has received an express acknowledgment from a participant tendering Initial Notes that are the subject of such book-entry confirmation, that such participant has received and agrees to be bound by the terms of the letter of transmittal and that the Company may enforce such agreement against such participant.

Guaranteed Delivery Procedures

If the procedures for book-entry transfer cannot be completed on a timely basis, a tender may be effected if:

•

the tender is made through an eligible institution;

•

prior to the Expiration Date, the exchange agent receives by facsimile transmission (if no signature guarantee is required), mail or hand delivery from such eligible institution a properly completed and duly executed letter of transmittal and notice of guaranteed delivery, substantially in the form provided by the Company, which:

(1)

sets forth the name and address of the holder of Initial Notes and identifies the Initial Notes tendered, including the principal amount of such Initial Notes;

(2)

states that the tender is being made thereby; and

(3)

guarantees that within three business days after the Expiration Date, the letter of transmittal and any other documents required by the letter of transmittal and certificates representing the Initial Notes in proper form for transfer, or a book-entry confirmation, will be deposited by the eligible institution with the exchange agent; and

•

a properly completed and executed letter of transmittal and any other documents required by the letter of transmittal as well as certificates representing all tendered Initial Notes in proper form for transfer, or a book-entry confirmation, are received by the exchange agent within three business days after the Expiration Date.

Withdrawal of Tenders

Tenders of Initial Notes may be withdrawn at any time prior to the Expiration Date.

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For a withdrawal to be effective, a written notice of withdrawal must be received by the exchange agent prior to the Expiration Date at the address set forth in the letter of transmittal. Any such notice of withdrawal must:

•

specify the name of the person having tendered the Initial Notes to be withdrawn;

•

identify the Initial Notes to be withdrawn, including the principal amount of such Initial Notes;

•

in the case of Initial Notes tendered by book-entry transfer, specify the number of the account at DTC from which the Initial Notes were tendered and specify the name and number of the account at DTC to be credited with the withdrawn Initial Notes and otherwise comply with the procedures of such facility;

•

contain a statement that such holder is withdrawing its election to have such Initial Notes exchanged;

•

be signed by the holder in the same manner as the original signature on the letter of transmittal by which such Initial Notes were tendered including any required signature guarantees, or be accompanied by documents of transfer to have the trustee with respect to the Initial Notes register the transfer of the Initial Notes in the name of the person withdrawing the tender; and

•

if certificates for Initial Notes have been transmitted, specify the name in which such Initial Notes are registered, if different from the person who tendered such Initial Notes.

All questions as to the validity, form, eligibility and time of receipt of such notice will be determined by the Company, which determination shall be final and binding on all parties. Any Initial Notes so withdrawn will be deemed not to have been validly tendered for exchange for purposes of the Exchange Offer. Tenders of Initial Notes will not be, or be deemed to have been, made if withdrawn. Any Initial Notes which have been tendered for exchange but which are not exchanged for any reason will be returned to the tendering holder thereof without cost to such holder, in the case of physically tendered Initial Notes, or credited to an account maintained with DTC for the Initial Notes promptly after withdrawal, rejection of tender or termination of the Exchange Offer. Properly withdrawn Initial Notes may be retendered by following one of the procedures described under “— Procedures for Tendering” and “— Book-Entry Transfer” above at any time prior to the Expiration Date.

Conditions

Notwithstanding any other provisions of the Exchange Offer, or any extension of the Exchange Offer, the Company will not be required to accept for exchange, or to exchange any Exchange Notes for, any Initial Notes and the Company may terminate the Exchange Offer or, at the Company’s option, modify, extend or otherwise amend the Exchange Offer, if any of the following conditions are not satisfied on or prior to the Expiration Date:

•

no action or event shall have occurred or been threatened, no action shall have been taken, and no statute, rule, regulation, judgment, order, stay, decree or injunction shall have been issued, promulgated, enacted, entered, enforced or deemed to be applicable to the Exchange Offer or the exchange of Initial Notes for Exchange Notes under the Exchange Offer by or before any court or governmental regulatory or administrative agency, authority, instrumentality or tribunal, including, without limitation, taxing authorities, that either:

(1)

challenges the making of the Exchange Offer or the exchange of Initial Notes for Exchange Notes under the Exchange Offer or might, directly or indirectly, be expected to prohibit, prevent, restrict or delay consummation of, or might otherwise adversely affect in any material manner, the Exchange Offer or the exchange of Initial Notes for Exchange Notes under the Exchange Offer; or

(2)

in the Company’s reasonable judgment, could materially adversely affect the Company’s (or the Company’s subsidiaries’) business, condition (financial or otherwise), income, operations, properties, assets, liabilities or prospects or materially impair the contemplated benefits to the Company of the Exchange Offer or the exchange of Initial Notes for Exchange Notes under the Exchange Offer;

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•

nothing has occurred or may occur that would or might, in the Company’s reasonable judgment, be expected to prohibit, prevent, restrict or delay the Exchange Offer or impair the Company’s ability to realize the anticipated benefits of the Exchange Offer;

•

there shall not have occurred: (a) any general suspension of or limitation on trading in securities in Canadian or United States securities or financial markets, whether or not mandatory, (b) any material adverse change in the prices of the Initial Notes that are the subject of the Exchange Offer, (c) a material impairment in the general trading market for debt securities, (d) a declaration of a banking moratorium or any suspension of payments in respect of banks by federal or state authorities in Canada or the United States, whether or not mandatory, (e) a commencement of a war, armed hostilities, a terrorist act or other national or international calamity directly or indirectly relating to Canada or the United States, (f) any limitation, whether or not mandatory, by any governmental authority on, or other event having a reasonable likelihood of affecting, the extension of credit by banks or other lending institutions in Canada or the United States, (g) any material adverse change in the securities or financial markets in Canada or the United States generally, or (h) in the case of any of the foregoing existing at the time of the commencement of the Exchange Offer, a material acceleration or worsening thereof; and

•

The Bank of New York Mellon, as trustee for the Initial Notes, shall have not been directed by any holders of Initial Notes to object in any respect to, nor take any action that could, in the Company’s reasonable judgment, adversely affect the consummation of the Exchange Offer or the exchange of Initial Notes for Exchange Notes under the Exchange Offer, nor shall the trustee have taken any action that challenges the validity or effectiveness of the procedures used by the Company in making the Exchange Offer or the exchange of Initial Notes for Exchange Notes under the Exchange Offer.

The foregoing conditions are for the Company’s sole benefit and may be asserted by the Company, regardless of the circumstances giving rise to any such condition, or may be waived by the Company, in whole or in part, at any time and from time to time in the Company’s reasonable discretion. All such conditions must be satisfied or waived by the Company, as applicable, at or before the expiration of the Exchange Offer.

If any of the foregoing conditions are not satisfied, the Company may, at any time on or prior to the Expiration Date:

•

terminate the Exchange Offer and promptly return all tendered Initial Notes to the respective tendering holders;

•

modify, extend or otherwise amend the Exchange Offer and retain all tendered Exchange Notes until the Expiration Date, as extended, subject, however, to the withdrawal rights of holders; or

•

waive the unsatisfied conditions with respect to the Exchange Offer and accept all Initial Notes tendered and not previously validly withdrawn.

The Company will not accept for exchange any Initial Notes tendered, and no Exchange Notes will be issued in exchange for any such Initial Notes, if at such time any stop order shall be threatened or in effect with respect to the registration statement of which this short form prospectus constitutes a part or the qualification of the Indenture under the Trust Indenture Act of 1939, as amended. The Company is required to use its commercially reasonable efforts to obtain the withdrawal of any order suspending the effectiveness of the registration statement at the earliest practicable date.

In addition, subject to applicable law, the Company may in its absolute discretion terminate the Exchange Offer for any other reason.

Exchange Agent

The Bank of New York Mellon has been appointed as exchange agent for the Exchange Offer. Questions and requests for assistance and requests for additional copies of this short form prospectus, or of the letter of transmittal, should be directed to the exchange agent as provided in the letter of transmittal.

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Fees and Expenses

The expenses of soliciting tenders pursuant to the Exchange Offer will be borne by the Company. The principal solicitation for tenders pursuant to the Exchange Offer is being made by mail; however, additional solicitations may be made by telephone, telecopy or in person by the Company’s officers and regular employees.

The Company will not make any payments to brokers, dealers or other persons soliciting acceptances of the Exchange Offer. The Company will, however, pay the exchange agent reasonable and customary fees for its services and will reimburse the exchange agent for its reasonable out-of-pocket expenses in connection therewith. The Company may also pay brokerage houses and other custodians, nominees and fiduciaries the reasonable out-of-pocket expenses incurred by them in forwarding copies of the short form prospectus and related documents to the beneficial owners of the Initial Notes, and in handling or forwarding tenders for exchange.

The expenses to be incurred by the Company in connection with the Exchange Offer will be paid by the Company, including fees and expenses of the exchange agent and trustee for the Initial Notes and accounting, legal, printing and related fees and expenses.

The Company will pay all transfer taxes, if any, applicable to the exchange of Initial Notes pursuant to the Exchange Offer. If, however, Exchange Notes or Initial Notes for principal amounts not tendered or accepted for exchange are to be registered or issued in the name of any person other than the registered holder of the Initial Notes tendered, or if tendered Initial Notes are registered in the name of any person other than the person signing the letter of transmittal, or if a transfer tax is imposed for any reason other than the exchange of Initial Notes pursuant to the Exchange Offer, then the amount of any such transfer taxes imposed on the registered holder or any other persons will be payable by the tendering holder. If satisfactory evidence of payment of such taxes or exemption therefrom is not submitted with the letter of transmittal, the amount of such transfer taxes will be billed directly to such tendering holder.

Consequences of Failure to Exchange

Holders of Initial Notes who do not exchange their Initial Notes for Exchange Notes pursuant to the Exchange Offer will continue to be subject to the restrictions on transfer of such Initial Notes as set forth in the legend thereon as a consequence of the issuance of the Initial Notes pursuant to exemptions from, or in transactions not subject to, (i) the registration requirements of the Securities Act and applicable state securities laws or (ii) the prospectus requirements of applicable securities laws in the provinces and territories of Canada, as applicable. The Initial Notes may not be offered, sold or otherwise transferred, except in compliance with (i) the registration requirements of the Securities Act, pursuant to an exemption from registration under the Securities Act or in a transaction not subject to the registration requirements of the Securities Act, and in compliance with applicable state securities laws or (ii) the prospectus requirements of applicable securities laws in the provinces and territories of Canada, or pursuant to an exemption therefrom or in a transaction not subject thereto, as applicable. The Company does not currently anticipate that it will register under the Securities Act the Initial Notes that are not tendered and accepted for purchase in the Exchange Offer, and the Company is not obligated to do so under the terms of the Registration Rights Agreement once the Exchange Offer is completed. To the extent that Initial Notes are tendered and accepted in the Exchange Offer, the trading market for any untendered and tendered but unaccepted Initial Notes could be adversely affected.

Interest on the Exchange Notes

The Exchange Notes will accrue interest at the rate of 3.375% per annum payable semi-annually in arrears in cash. The Exchange Notes will accrue interest from and including the last interest payment date on which interest was paid on the Initial Notes surrendered in exchange therefor or, if no interest has been paid on such Initial Notes, from the issue date of such Initial Notes; provided that if Initial Notes are surrendered for exchange on or after a record date for an interest payment date that will occur on or after the date of such exchange and as to which interest will be paid, interest on the Exchange Notes received in exchange therefor will accrue from the date of such interest payment date. Interest on the Exchange Notes is payable on March 3 and September 3, beginning on September 3, 2021. No additional interest will be paid on Initial Notes tendered and accepted for exchange.

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INSURANCE REGULATORY MATTERS

We are subject to regulation under the insurance laws of the various jurisdictions in which our operating insurance subsidiaries are domiciled or conduct business.

The following is a summary of the principal insurance regulatory considerations in the United States, Canada, Bermuda and the United Kingdom, being the jurisdictions in which we conduct the majority of our business.

United States

General

Our United States operating insurance subsidiaries are subject to extensive regulation throughout the United States. Although there is limited federal regulation of the insurance business in the United States, each state has a comprehensive system for regulating insurers operating in that state. The laws of the various states establish supervisory agencies with broad authority to regulate, among other things, licenses to transact business, premium rates, trade practices, market conduct, agent licensing, policy forms, underwriting and claims practices, insurance policy termination, reserve adequacy, permissible investments, governance and insurer solvency. States also regulate investment activities on the basis of quality, distribution and other quantitative criteria. Further, most states compel participation in and regulate composition of various shared market or residual market mechanisms. States have also enacted legislation that regulates insurance holding company systems, including acquisitions, dividends, the terms of affiliate transactions, and other related matters. Our United States operating insurance subsidiaries are domiciled in Arkansas, California, Connecticut, Delaware, New Hampshire, New Jersey and New York.

Insurance companies are also affected by a variety of state and federal legislative and regulatory measures and judicial decisions that define the scope of the risks and benefits for which insurance is sought and provided. These include redefinitions of risk exposure in such areas as product liability, environmental damage and workers’ compensation. In addition, individual state insurance departments may limit premium rates for some classes of insureds and prevent the insurance companies from charging rates adequate to reflect the level of risk assumed by the insurer for those classes. Such developments may result in adverse effects on the profitability of various lines of insurance. In some cases, these adverse effects on profitability can be minimized, when possible, through the repricing of coverages if permitted by applicable regulations, or the limitation or cessation of the affected business, which may be restricted by state law.

Most states have insurance laws requiring that for certain lines of property and casualty insurance rate schedules, policy or coverage forms, and other information be filed with each such state’s regulatory authority. In many cases, such rates and/or policy forms must be approved prior to use. A few states have considered or enacted limitations on the ability of insurers to share data used to compile rates. Such limitations have had, and are expected to have, no significant impact on us.

Insurance companies are required to file detailed annual and quarterly financial reports with the state insurance regulators in each of the states in which they do business, and their business and accounts are subject to examination by such regulators at any time. In addition, these insurance regulators periodically examine each insurer’s financial condition, adherence to statutory accounting practices, and compliance with insurance department rules and regulations, including market conduct and claims practices.

Insurance Regulation Concerning Change or Acquisition of Control

The insurance codes in our operating insurance subsidiaries’ respective domiciliary states each contain similar provisions (subject to certain variations) to the effect that the acquisition of “control” of a domestic insurer or of any person that directly or indirectly controls a domestic insurer cannot be consummated without the prior approval of the domiciliary insurance regulator. In general, a presumption of “control” arises from the direct or indirect ownership, control, possession with the power to vote or possession of proxies with respect to 10% or more of the outstanding voting securities of a domestic insurer or of a person that controls a domestic insurer. A person seeking to acquire control, directly or indirectly, of a domestic insurance company or of any person controlling a domestic insurance company generally must file with the relevant insurance regulatory authority a statement relating to the acquisition of control containing certain information regarding

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the proposed acquisition and acquiring party required by statute and regulations, provide a copy of such statement to the domestic insurer and obtain the prior approval of such regulatory authority for the acquisition. In addition, certain state insurance laws contain provisions that require pre-acquisition notification to the state insurance regulator of a change of control of a non-domestic insurance company licensed in that state. Such pre-acquisition notification statutes authorize certain remedies, including the issuance of cease and desist orders with respect to the non-domestic licensed insurer and its affiliates doing business in the state if certain conditions exist, such as undue market concentration. Additionally, in most states, the insurance regulator is authorized to deny an application to acquire control of a domestic insurer if the acquisition of control of the domestic insurer would substantially lessen competition in insurance in the state or tend to create a monopoly.

These laws regulating change of control may discourage potential acquisition proposals and may delay, deter or prevent a change of control of Fairfax, including through transactions and in particular unsolicited transactions, that some or all of our shareholders might consider to be desirable.

Regulation of Dividends and Other Payments

We are a legal entity separate and distinct from our subsidiaries. As a holding company with no other business operations, our primary sources of cash to meet our obligations, including principal and interest payments with respect to indebtedness and preferred share dividend payments, are available dividends and other statutorily permitted payments, such as tax allocation payments and management and other fees, from our operating insurance subsidiaries. Our operating insurance subsidiaries are subject to various statutory and regulatory restrictions in their respective states of domicile that limit the amount of dividends or distributions an insurance company may pay to its shareholders without prior regulatory approval. Ordinary dividends, for which no regulatory approval is generally required, are limited to amounts determined by formula, which varies by state. The formula typically is based on the level of statutory surplus at the end of the prior year, as well as on some measure of statutory earnings for the prior year, in relation to total dividends paid during the prior 12 months. In addition, dividends generally may be paid only out of “earned surplus” as defined by each state. In every case, capital and surplus subsequent to the payment of any dividends must be reasonable in relation to an insurance company’s outstanding liabilities and must be adequate to meet its financial needs. For these purposes, both surplus and earnings are determined in accordance with Statutory Accounting Principles (“SAP”), which differs in certain respects from IFRS and U.S. generally-accepted accounting principles.

No assurance can be given that some or all of our operating insurance subsidiaries’ domiciliary states will not adopt statutory provisions more restrictive than those currently in effect.

If insurance regulators determine that payment of a dividend or any other payments to an affiliate (such as payments under a tax-sharing agreement or payments for employee or other services) would, because of the financial condition of the paying insurance company or otherwise, result in such insurance company being in a hazardous financial condition or would otherwise be prohibited by applicable law, the regulators may prohibit such payments that would otherwise be permitted without prior approval.

Statutory Surplus, Risk-Based Capital and Group Capital

An insurance regulator may limit or prohibit the writing of new business by an insurance company within its jurisdiction when, in the regulator’s judgment, the insurance company is not maintaining adequate statutory capital and surplus. We do not currently anticipate that any regulator would limit the amount of new business that our operating insurance subsidiaries may write given their current levels of statutory capital and surplus.

In order to enhance the regulation of insurer solvency, the National Association of Insurance Commissioners (“NAIC”) established risk-based capital (“RBC”) requirements for property and casualty insurance companies. These RBC requirements, which have been adopted in all of the states in which our operating insurance subsidiaries are domiciled, are designed to assess capital adequacy and raise the level of protection that statutory surplus provides for policyholder obligations. The NAIC RBC model law provides that, for property and casualty insurers, the RBC formula will take into account: (i) underwriting risk; (ii) asset risk; (iii) credit risk; and (iv) all other business risks and such other relevant risks as are set forth in the NAIC’s

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Property/Casualty RBC Instructions. The RBC formula provides a mechanism for the calculation of an insurance company’s Authorized Control Level (“ACL”) RBC amount.

The NAIC RBC model law stipulates four levels of regulatory action depending on how an insurer’s statutory surplus compares to its RBC. The initial level, the “Company Action Level,” requires the insurance company to submit a plan of corrective action to the relevant insurance commissioner if its surplus falls below 200% of the ACL amount (or below 300% of the ACL amount, when a “trend test” is triggered under the NAIC’s Property/Casualty RBC Instructions). The next level, the “Regulatory Action Level,” requires the company to submit a plan of corrective action and also allows the regulator to perform an examination of the company’s business and operations and issue a corrective order if the surplus falls below 150% of the ACL amount (or other triggering events specified in the RBC model law occur). The third level, the ACL, permits the regulator to place the company under regulatory control, including rehabilitation or liquidation, if its surplus falls below 100% of that amount (or other triggering events specified in the RBC model law occur). The final action level, the “Mandatory Control Level,” requires the insurance commissioner to place the company under regulatory control if its surplus falls below 70% of the ACL amount.

In addition, the NAIC has developed a group capital calculation tool using an RBC aggregation methodology. The group capital calculation is designed to assist state insurance regulators in understanding the financial condition of non-insurance entities that are part of an insurance holding company system and the degree to which insurance companies are supporting those non-insurance entities.

In 2019, the International Association of Insurance Supervisors (“IAIS”) adopted the Common Framework for Supervision of Internationally Active Insurance Groups (“ComFrame”) to establish minimum standards for the supervision of internationally active insurance groups (“IAIGs”). IAIS members (including supervisors of various Fairfax insurance subsidiaries) have committed to implementing ComFrame and the IAIS is expected to assess each IAIS member’s compliance with ComFrame requirements going forward. Fairfax has been designated as an IAIG with the Delaware Insurance Commissioner as its group-wide supervisor.

ComFrame includes an Insurance Capital Standard (“ICS”), a risk-based, group-wide capital standard for IAIGs. Beginning in 2025, IAIS members are required to implement ICS as a group-wide prescribed capital requirement for IAIGs or a group-wide capital requirement that provides comparable outcomes to ICS. In the United States, the NAIC’s group capital calculation is intended to serve as an alternative methodology that provides a comparable outcome to ICS. If accepted by the IAIS, the United States will be deemed in compliance with ComFrame’s ICS requirement. The impact of ICS and the group capital calculation on the Company are uncertain; however, they may result in an increase in the level of capital and liquidity required by insurance holding companies.

NAIC IRIS Ratios

The NAIC has developed a set of financial relationships or “tests” called the Insurance Regulatory Information System (“IRIS”) that was designed to facilitate early identification of companies that may warrant special attention by insurance regulatory authorities. IRIS identifies 13 industry ratios (referred to as “IRIS ratios”) and specifies “usual ranges” for each ratio. An IRIS ratio that falls outside the usual range is not necessarily considered adverse. An insurance company may fall out of the usual range for one or more ratios because of specific transactions that are in themselves immaterial or eliminated at the consolidated level. Generally, an insurance company may become subject to increased regulatory scrutiny if it falls outside the usual ranges on multiple ratios.

Investment Regulation

Our operating subsidiaries are subject to state laws and regulations that require diversification of investment portfolios and that limit the amount of investments in certain investment categories. Failure to comply with these laws and regulations may cause non-conforming investments to be treated as non-admitted assets for purposes of measuring statutory surplus and, in some instances, would require divestiture. As of the date of this short form prospectus, we believe our investments comply with such laws and regulations in all material respects.

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Credit for Reinsurance and Licensing

A primary insurer ordinarily will enter into a reinsurance agreement only if it can obtain credit for the reinsurance ceded on its U.S. statutory financial statements. In general, credit for reinsurance is allowed in the following circumstances: (1) if the reinsurer is licensed in the state in which the primary insurer is domiciled; (2) if the reinsurer is an “accredited” or otherwise approved reinsurer in the state in which the primary insurer is domiciled; (3) in some instances, if the reinsurer (a) is domiciled in a state that is deemed to have substantially similar credit for reinsurance standards as the state in which the primary insurer is domiciled and (b) meets certain financial requirements; or (4) if none of the above apply, to the extent that the reinsurance obligations of the reinsurer are collateralized appropriately, typically through the posting of a letter of credit for the benefit of the primary insurer, the deposit of assets into a trust fund established for the benefit of the primary insurer, or by the primary insurer retaining as collateral for the reinsurer’s obligations, assets that would otherwise be transferred by the primary insurer to the reinsurer as consideration for the reinsurance. Most states have adopted provisions of the NAIC amendments to its Credit for Reinsurance Model Law and Regulation that allow full credit to U.S. ceding insurers for reinsurance ceded to qualified reinsurers (called “certified reinsurers”) that do not otherwise satisfy the state’s credit for reinsurance requirements based upon less than 100% collateralization. Under those provisions, collateral requirements may be reduced for reinsurers meeting certain criteria as to financial strength and reliability that are domiciled in jurisdictions that are found to have strong systems of insurance regulation.

These credit for reinsurance provisions are changing. The Dodd-Frank Wall Street Reform and Consumer Protection Act (“Dodd-Frank”) that was enacted in 2010 authorizes the Federal Insurance Office (“FIO”) within the Department of Treasury to assist the Treasury Secretary in negotiating “covered agreements” between the United States and one or more foreign governments or regulatory authorities that address prudential measures with respect to the business of insurance or reinsurance. Where a state law is inconsistent with a “covered agreement” and provides less favorable treatment to foreign insurers than U.S. companies, the FIO Director may preempt conflicting state law. On September 22, 2017, the United States and the European Union (“EU”) entered into a covered agreement (the “EU Covered Agreement”) that, among other things, would eliminate reinsurance collateral and local presence requirements for qualified U.S. reinsurers operating in the EU insurance market, and eliminate reinsurance collateral and local presence requirements for qualified EU reinsurers operating in the U.S. insurance market. On December 18, 2018, the United States and the United Kingdom entered into a covered agreement (“UK Covered Agreement”) that extends terms nearly identical to the EU Covered Agreement to insurers and reinsurers operating in the United Kingdom now that the United Kingdom has left the European Union. On June 25, 2019, the NAIC adopted amendments to the Credit for Reinsurance Model Law and Regulation that, once adopted by the various states, would implement the EU Covered Agreement and the UK Covered Agreement and eliminate reinsurance collateral requirements for qualified reinsurers operating in the United States that are domiciled in other jurisdictions deemed “Reciprocal Jurisdictions.” If states fail to adopt these amendments by September 2022, then existing state reinsurance collateral requirements may be preempted with respect to qualified EU and U.K. reinsurers. As of September 1, 2021, the NAIC reports that forty-five states have adopted the 2019 amendments to the Credit for Reinsurance Model Law and an additional two are considering the amendments.

While the elimination or reduction of regulatory requirements for collateral for reinsurance ceded to qualified reinsurers domiciled in Reciprocal Jurisdictions or “certified reinsurers” does not prevent our operating entities in the United States from continuing to request collateral, it is unclear how much collateral our United States operating entities will be able to obtain from these reinsurers going forward. In addition, it is unclear whether these changes will affect the competitive position of any of our United States and non-United States reinsurance subsidiaries.

Guaranty Funds

Virtually all U.S. states have separate insurance guaranty fund laws requiring property and casualty insurance companies licensed to do business in their respective jurisdictions to be members of their guaranty associations. These associations are organized to pay covered claims (as defined and limited by the various guaranty association statutes) under insurance policies issued by insolvent insurance companies. These associations generally levy assessments (up to prescribed limits) on all member insurers in a particular state on the basis of the proportionate share of the premiums written by member insurers in the covered lines of

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business in that state. Maximum assessments permitted by law in any one year generally vary between 1% and 2% of annual premiums written in the covered lines by a member in that state. Some states permit or require member insurers to recover assessments paid through surcharges on policyholders or through full or partial premium tax offsets, while other states permit recovery of assessments through the rate filing process.

Our policy is to accrue for insolvencies when the loss is probable and the assessment amount can be reasonably estimated. In the case of most insurance insolvencies, our ability to reasonably estimate the insolvent insurer’s liabilities or develop a meaningful range of the insolvent insurer’s liabilities is significantly impaired by inadequate financial data with respect to the estate of the insolvent company as supplied by the guaranty funds. Although the amounts of any future assessments by guaranty funds cannot be predicted with certainty, we believe that future guaranty association assessments for known insurer insolvencies will not have a material adverse effect on our results of operations or financial condition.

Shared Markets

As a condition of their licenses to do business, some of our operating insurance subsidiaries are required to participate in mandatory property and casualty shared market mechanisms, residual markets or pooling arrangements, which provide various types of insurance coverage to individuals or other entities that are otherwise unable to purchase such coverage in the commercial insurance marketplace. Our United States operating insurance subsidiaries’ participation in such shared markets or pooling mechanisms is generally proportionate to the amount of each of our operating insurance subsidiaries’ direct premiums written for the type of coverage written by the specific pooling mechanism or residual market mechanism in the applicable state.

Many states have laws that establish second-injury funds to provide compensation to injured employees for aggravation of a prior condition or injury. Generally, insurers writing workers’ compensation in those states that have second-injury funds are subject to the laws creating the funds, including the various funding mechanisms that those states have adopted to fund the second-injury funds, including premium surcharges that effectively pass the cost of the fund on to policyholders.

Certain of our operating insurance subsidiaries participate in the Florida Hurricane Catastrophe Fund, a state mandated catastrophe reinsurance fund. Business insurance is also subject to pooled insurance on a small scale for commercial properties insured through the various Fair Access to Insurance Requirements Plans that exist in most states.

The amount of future losses or assessments from the shared and residual market mechanisms and pooling arrangements described above cannot be predicted with certainty. The underwriting results of these pools traditionally have been unprofitable. Although it is possible that future losses or assessments from such mechanisms and pooling arrangements could have a material adverse effect on our results of operations, we do not expect future losses or assessments from the shared and residual market mechanisms and pooling arrangements to have a material adverse effect on our liquidity or capital resources.

Insolvency of Insurers

Insolvency proceedings for United States insurance companies, including reinsurers, are generally conducted pursuant to state insurance law. In the event one of our United States operating insurance subsidiaries becomes insolvent or otherwise is found by its domiciliary regulator to be in a hazardous financial condition as provided under applicable state insurance law, insolvency proceedings, up to and including rehabilitation, conservation and liquidation, would be initiated by the insurance regulator of the state in which the subsidiary is domiciled, which would serve as the domestic receiver of its properties, assets and business. Insurance regulators located in other states in which we conduct business may have jurisdiction over assets or properties located in such states under certain circumstances. In an insolvency proceeding, policyholders’ claims would have priority over investors’ claims.

Privacy Regulation

We are subject to a number of U.S. federal and state laws and regulations that require financial institutions and other businesses to protect the confidentiality of individual’s personal information. The Gramm Leach

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Bliley Act and regulations promulgated thereunder govern the privacy of consumer financial information. The regulations set standards for the protection of, and limits disclosure by, financial institutions of “nonpublic personal information” about individuals who obtain financial products or services for personal, family, or household purposes. A variety of state privacy statutes and regulations also govern the privacy of information about consumers and require notification to state authorities and individuals if certain personally identifiable information is subject to unauthorized access or disclosure. States, like New York State under its SHIELD Act, have also begun to expand upon the definition of personal information that requires protection and notification in cases of a breach, to include biometric information, genetic information, and email addresses with their corresponding passwords or security questions and answers. In June 2018, the State of California enacted the California Consumer Privacy Act of 2018 (“CCPA”), which came into effect on January 1, 2020 and requires companies that process information that can be tied to identifiable California residents to make new disclosures to California residents about their data collection, use and sharing practices, and provides certain new rights, including allowing individuals to opt out of certain data sharing with third parties. The statute also creates a new cause of action where an individual’s personal information is subject to a data breach due to a business’s failure to implement and maintain reasonable security practices. Additionally, California voters approved the California Privacy Rights Act of 2020 (“CPRA”) as part of the November 2020 ballot. The CPRA substantially amends the CCPA, and it becomes fully effective on January 1, 2023. New comprehensive privacy laws have also recently been passed in Colorado and Virginia. There are also a number of legislative proposals pending before the U.S. Congress and various state legislative bodies concerning privacy. Privacy regulation is an evolving area of state and federal regulation, which requires us to continue to monitor developments.

Cybersecurity

In 2017, the NAIC adopted an Insurance Data Security Model Law (#668-1) that establishes minimum cybersecurity requirements applicable to licensed insurance companies and licensed insurance intermediaries. Among other requirements, the Insurance Data Security Model Law requires licensees to maintain an information security program based on a cybersecurity risk assessment, establish a written incident response plan, provide an annual certification of compliance to state insurance regulators, and investigate and notify state insurance regulators regarding cybersecurity events. Approximately one third of states have adopted a version of the Insurance Data Security Model Law, and additional states are expected to do so in the future. The New York Department of Financial Services already has a similar cybersecurity regulation in effect. Separately, Massachusetts also has regulations in place that require businesses to maintain a cybersecurity program that meets certain minimum requirements. See also “Risk Factors — A disruption of our information technology systems could significantly affect our business.”

Regulation of Holding Company Systems

While insurance in the United States is regulated primarily on a legal-entity basis, the NAIC has increased its focus on risks presented by an insurer’s holding company system. In 2010, the NAIC adopted revisions to the Insurance Holding Company System Regulatory Act and the Insurance Holding Company System Model Regulation (together, the “Revised Model Holding Company Act and Regulation”) that include, among other amendments, a requirement for the ultimate controlling person of every insurer to file an enterprise risk report annually. “Enterprise risk” is defined as any activity, circumstance, event or series of events involving one or more affiliates of an insurer that, if not remedied promptly, is likely to have a material adverse effect upon the financial condition or liquidity of the insurer or its insurance holding company system as a whole. The Revised Model Holding Company Act and Regulation have been substantively adopted in each of our operating insurance subsidiaries’ domiciliary states.

In 2012, the NAIC adopted the Risk Management and Own Risk and Solvency Assessment (“ORSA”) Model Act, which has been substantively adopted in each of our operating insurance subsidiaries’ domiciliary states. The ORSA Model Act requires insurers or their insurance group to conduct an ORSA consistent with a process comparable to the NAIC ORSA Guidance Manual no less than annually and at any time when there are significant changes to the risk profile of the insurer or the insurance group of which the insurer is a member. An ORSA is a confidential internal assessment, appropriate to the nature, scale and complexity of an insurer or insurance group, conducted by that insurer or insurance group of the material and relevant risks associated with the insurer or insurance group’s current business plan, and the sufficiency of capital resources

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to support those risks. The assessments must be documented in an annual summary report, a copy of which must be submitted to state insurance regulators as required under the applicable laws of each state.

The NAIC has also developed a group capital calculation tool using an RBC aggregation methodology. The group capital calculation is designed to assist state insurance regulators in understanding the financial condition of non-insurance entities that are part of an insurance holding company system and the degree to which insurance companies are supporting those non-insurance entities. See Insurance Regulatory Matters — United States — Statutory Surplus, Risk Based Capital and Group Capital.

Corporate Governance Annual Disclosure Model Act

The NAIC has adopted the Corporate Governance Annual Disclosure Model Act (“CGAD”). CGAD requires an annual filing by an insurer or insurance group that provides a detailed report on corporate governance structure and policies and procedures. Fairfax submits CGAD filings on behalf of all of its United States operating insurance subsidiaries to the Delaware Department of Insurance.

Terrorism Risk Insurance Act

The Terrorism Risk Insurance Act of 2002, as amended (“TRIA”), established a program under which the U.S. federal government will share with the insurance industry the risk of loss from certain acts of terrorism certified as such by the Secretary of the Treasury. The program was most recently extended in 2019 through December 31, 2027. Under the current program (i) the threshold for the program to go into effect (the triggering event) is $200 million in insured losses, (ii) the insurer deductible is 20% of the insurer’s affiliated group’s direct earned premium for the prior year from qualified property and casualty insurance lines, and (iii) the amount that insurers must cover as a whole through co-payments and deductibles, which is known in the industry as the aggregate retention, is $37.5 billion. TRIA is applicable to almost all commercial lines of property and casualty insurance but excludes commercial auto, burglary and theft, surety, professional liability and farm owners’ multi-peril insurance. Insurers with direct commercial property and casualty insurance exposure in the United States are required to participate in the program and make available coverage for certified acts of terrorism. Federal participation will be triggered when the Secretary of Treasury certifies an act of terrorism.

While the provisions of TRIA and the purchase of certain terrorism reinsurance coverage mitigate our exposure in the event of a large-scale terrorist attack, the risk of severe losses to us from acts of terrorism remains because our effective deductible is significant, certain lines that we write are not covered by TRIA and there is no certainty that future acts of terrorism will be certified as such by the Treasury Secretary. There is also no certainty that the program will be extended beyond December 31, 2027, or if it is extended that the program will provide coverage in the same amounts and on the same terms. Moreover, regardless of TRIA, some state insurance regulators do not permit terrorism exclusions for various coverages or causes of loss. Accordingly, we continue to monitor carefully our concentrations of risk.

Possible Legislative and Regulatory Changes

In recent years, the insurance industry has been subject to increased scrutiny by regulators and legislators. As noted above, the NAIC and a number of state legislatures have considered or adopted legislative proposals that alter and, in many cases, increase the authority of state regulators to regulate insurance companies and holding company systems. Additional regulations or new requirements may emerge from activities of various regulatory entities, including the Federal Reserve Board, FIO, the Financial Stability Oversight Council, and the NAIC. We cannot predict whether any specific state or federal measures will be adopted to change the nature or scope of the regulation of insurance or what effect any such measures would have on Fairfax and its United States operating insurance subsidiaries.

Finally, the ongoing investigations discussed above of insurance industry business practices may result in new laws or regulations at the state or federal level. See “Risk Factors — Certain business practices of the insurance industry have been the subject of negative publicity and investigations by government authorities and the subject of class action litigation.”

It is not possible to predict the outcome of any of the foregoing legislative, administrative or congressional activities or the potential effects thereof on us.

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Canada

General

Each of our Canadian insurance subsidiaries is federally incorporated under the Insurance Companies Act (“ICA”) and is licensed under insurance legislation in each of the provinces and territories in which it operates.

The ICA and provincial legislation require the filing by our Canadian insurance subsidiaries of annual and other reports on their financial condition and results. The ICA imposes restrictions on transactions with related parties and sets forth requirements governing reserves for actuarial liabilities and the safekeeping of assets and other matters. The ICA is administered, and the activities of our insurance subsidiaries are supervised, by the Office of the Superintendent of Financial Institutions (“OSFI”). OSFI conducts examinations to ensure compliance with the ICA and to confirm the financial condition of the companies.

Investment Powers

Under the ICA, the directors of a federally incorporated insurance company must establish and the insurance company must adhere to investment and lending policies, standards and procedures that a reasonable and prudent person would apply to a portfolio of investments and loans to avoid undue risk of loss and obtain a reasonable return, subject to certain overall limitations on the amount it may invest in certain classes of investments, such as commercial loans, real estate and equities. Additional restrictions (and in some cases, the need for regulatory approvals) limit the nature of an insurance company’s investments.

Capital Requirements

Property and casualty insurers are required to meet a Minimum Capital Test (“MCT”) that assesses the insurer’s capital available to capital required. Federally regulated property and casualty insurers, including our Canadian insurance subsidiaries, must maintain available capital equal to at least the minimum capital requirement. OSFI expects insurers to establish a target capital level above the minimum requirement, and to maintain ongoing capital, at no less than the supervisory target of 150% of the MCT amount. OSFI expects federally regulated property and casualty insurers to establish an internal target capital ratio, and maintain ongoing capital, above the supervisory target. OSFI may, however, on a case-by-case basis, establish in consultation with an insurer an alternate supervisory target based upon the company’s risk profile. The ICA requires property and casualty insurance companies to maintain adequate levels of capital and adequate and appropriate liquidity. The MCT calculates the required capital by reference to, and varying with, the risk characteristics of each category of on and off-balance sheet assets held by the company, the company’s policy liabilities and reinsurance receivable and recoverable. This MCT calculation typically requires the application of quantitative factors to assets, as well as to certain off-balance sheet items, based on a number of prescribed risk components. The calculation of policy liabilities takes into account the risk associated with variations in claims, provisions, possible inadequacy of provisions for unearned premiums, possible inadequacy of provisions for premium deficiencies, and the occurrence of catastrophes. The calculation of reinsurance receivable and recoverable includes the risk of default for recoverables from reinsurers arising from both credit and actuarial risk.

Restrictions on Dividends and Capital Transactions

The ICA prohibits the declaration by the directors of a federally incorporated insurance company, or the payment by the insurance company, of any dividend on shares of an insurance company if there are reasonable grounds to believe the company is, or the payment of the dividend would cause the company to be, in contravention of applicable capital and liquidity requirements. The ICA also requires the directors of an insurance company to notify the Superintendent of Financial Institutions of the declaration of a dividend at least 15 days prior to the date fixed for its payment. Similarly, the ICA prohibits the purchase for cancellation of any shares issued by an insurance company or the redemption of any redeemable shares or other similar capital transactions, if there are reasonable grounds for believing that the company is, or the payment would cause the company to be, in contravention of its applicable capital and liquidity requirements. These latter transactions would also require the prior approval of the Superintendent of Financial Institutions. On March 13, 2020, OSFI announced that it expected all Canadian federally regulated financial institutions

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(including our Canadian insurance subsidiaries) to immediately halt all dividend increases and share buybacks. OSFI has not provided any specific time line as to when it will change this expectation.

Constraints on Shares

The ICA contains certain restrictions on the purchase or other acquisition, issue, transfer and voting of any shares of an insurance company. Pursuant to these restrictions, no person is permitted to acquire shares of any of our Canadian insurance subsidiaries, or to acquire control of a company which holds such an interest, if the acquisition would cause the person to have a “significant interest,” or increase an existing “significant interest,” in any class of shares of the insurance company, unless the prior approval of the Minister of Finance (Canada) is obtained. In addition, no insurance company is permitted to record any transfer or issue of its shares if the transfer or issue would cause the person to have a significant interest, or increase an existing significant interest, in the insurance company and such interest or increase has not been approved by the Minister of Finance (Canada). No person who has a significant interest in such a company may exercise any voting rights attached to the shares held by such person, or entities controlled by that person, unless the prior approval of the Minister of Finance (Canada) is obtained. In certain cases, if a person contravenes any of these restrictions, the Minister of Finance (Canada) may, by order, direct that person to dispose of all or any portion of those shares. For these purposes, a person has a significant interest in a class of shares of an insurance company where the aggregate of any shares of that class beneficially owned by that person, or an entity controlled by that person and by any person associated or acting jointly or in concert with that person, exceeds 10% of all outstanding shares of that class of shares of the company.

Provincial and Territorial Insurance Regulation

Each of our insurance subsidiaries is subject to provincial and territorial regulation and supervision in each of the provinces and territories of Canada in which it carries on business. Provincial insurance regulations deal primarily with the form and content of insurance contracts, the sale and marketing of insurance products, including licensing and supervision of insurance distributors, and the settlement of insurance claims. In the provinces of Alberta, Ontario, New Brunswick, Newfoundland and Labrador, Nova Scotia and Prince Edward Island premium rates for automobile insurance are regulated by public authorities. They require insurers to submit proposed rates to a regulatory body and have them approved before use. While Québec has a public auto insurance system for its base coverage, rates for excess insurance must be approved by the provincial insurance regulator. The approval process may also involve a hearing. Under provincial regulation, insurance contracts are deemed automatically to include certain terms that cannot be changed without the approval of the relevant regulatory authority, as well as certain terms that cannot be changed without statutory or regulatory amendment.

Property and Casualty Insurance Compensation Corporation (“PACICC”)

PACICC was formed to respond to claims by Canadian policyholders and refund certain premiums paid in advance, within limits, in the event of the insolvency of their insurance company. The Canadian property and casualty insurance industry elects the directors of PACICC. PACICC is funded by its member insurance companies, including our Canadian property and casualty insurance subsidiaries.

United Kingdom

General

We are subject to regulation and supervision by the Prudential Regulation Authority (“PRA”) and the Financial Conduct Authority (“FCA”) in relation to the carrying on by certain of our operating subsidiaries of regulated activities in the United Kingdom. We are also subject to regulatory standards set by Lloyd’s of London (“Lloyd’s”) by way of our operations in the Lloyd’s market.

Our U.K. operating subsidiaries include the following Lloyd’s managing agents:

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Brit Syndicates Limited, which is the managing agent of Syndicate 2987 (of which Brit UW Limited is the sole member);

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Newline Underwriting Management Limited, which is the managing agent of Syndicate 1218; and

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Allied World Managing Agency Limited, which is the managing agent of Syndicate 2232.

We also operate in the United Kingdom through a branch of AWAC Europe, an Irish insurance company registered with the Central Bank of Ireland, pursuant to the TPR (as defined below).

U.K. Regulatory Framework

Dual-regulation by PRA and FCA

The PRA and the FCA are the regulators for persons authorized under the Financial Services and Markets Act 2000 (“FSMA”) to undertake regulated activities in the financial services sector in the United Kingdom. The PRA oversees and is responsible for the micro-prudential regulation of banks, insurers and some large investment firms (the Financial Policy Committee, a sub-committee of the Bank of England, is responsible for macro-prudential regulation in the U.K.). The FCA is responsible for conduct of business regulation and market regulation for all authorized firms, and the prudential regulation of firms not authorized by the PRA.

Each of the Lloyd’s managing agents referred to above is authorized and regulated by the PRA as well as having its conduct of business regulated by the FCA and is, therefore, considered a dual-regulated firm. The PRA and the FCA have extensive powers to supervise and intervene in the affairs of regulated firms, for example, if they consider it appropriate in order to protect policyholders against the risk that the firm may be unable to meet its liabilities as they fall due, that the Threshold Conditions (as defined below) may not be met, that the firm or its parent has failed to comply with obligations under the relevant legislation or rules, that the firm has furnished them with misleading or inaccurate information or that there has been substantial departure from any proposal or forecast submitted to the relevant regulator.

The PRA and the FCA also have the power to take a range of disciplinary and enforcement actions in relation to a breach by a firm of FSMA or the rules made under FSMA as set out in the PRA Rulebook and other guidance and supervisory statements that the PRA may publish from time to time (the “PRA Rulebook”) and in the FCA Handbook of Rules and Guidance (the “FCA Handbook”), respectively. Such disciplinary and enforcement actions may include private censure, public censure, restitution, fines or sanctions and the award of compensation. The PRA (or, where relevant, the FCA) may also cancel or vary (including by imposing limitations on) a Part 4A permission (described in greater detail below) of a firm.

Lloyd’s of London

The Society of Lloyd’s is itself authorized by the PRA and regulated by the PRA and the FCA and its senior personnel are required to be approved by the regulators. Lloyd’s regulated activities include arranging deals in contracts of insurance written at Lloyd’s (“the basic market activity”), arranging deals in participations in Lloyd’s syndicates (“the secondary market activity”) and carrying out any activity in connection with, or for the purposes of, these two activities (article 14 of the Financial Services Act 2012 (Transitional Provisions) (Permission and Approval) Order 2013).

The Council of Lloyd’s (“Council”) is the governing body of the Lloyd’s market and under the Lloyd’s Act 1982 (the “1982 Act”) it is responsible for the market’s management and supervision. Under the 1982 Act, the Council has the power to regulate and direct the business of the market, and to make by-laws. Lloyd’s market rules are set out in the by-laws, and in other guidance, codes of conduct, minimum standards and bulletins issued by the Council or under its authority, although regulation of the Lloyd’s market is under the ultimate direction of the PRA and the FCA.

Lloyd’s does not carry on insurance activity itself, but regulates its members doing so. Members of Lloyd’s form and underwrite all insurance business via syndicates which consist of one or more such members. Lloyd’s supervises its own members (including in relation to setting the amount of capital required to be provided by each member to support its underwriting liabilities) under the direction of the PRA and the FCA. Members are not required to be authorized under FSMA but must abide by the Lloyd’s rules which means that they are indirectly regulated by the PRA and the FCA (given that Lloyd’s itself is a dual-regulated firm). Under sections 316 and 318 of FSMA, the PRA and the FCA can give directions to Lloyd’s or its members in order to advance one or more of their statutory objectives, for example by imposing particular rules on members.

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Lloyd’s has a memorandum of understanding with the PRA and the FCA to assist with cooperation in supervision and enforcement.

As regards prudential requirements, the rules in the Solvency II Firms section of the PRA Rulebook apply to Lloyd’s and its managing agents as a whole with some modifications (see “Prudential and capital requirements” below).

Syndicates are managed by managing agents who are authorized by the PRA and regulated by the PRA and the FCA.

Regulation of Lloyd’s Managing Agents

Part 4A Permissions

Under section 19 of FSMA, it is unlawful to carry on the regulated business of being a Lloyd’s managing agent in the United Kingdom without permission to do so from the PRA under Part 4A of FSMA (“Part 4A Permission”). A Lloyd’s managing agent will hold permissions for managing the underwriting capacity of a Lloyd’s syndicate as a managing agent at Lloyd’s, and usually also for insurance mediation activities such as dealing in investments as agent, arranging, advising on investments, and assisting in the administration and performance of contracts of insurance. Each of the above managing agents holds permission for managing the underwriting capacity of a Lloyd’s syndicate and one or more of the insurance mediation activities.

At the point of authorization (on the granting of Part 4A Permissions) and at all times thereafter, managing agents must meet specified threshold conditions which are set out in Schedule 6 of FSMA (“Threshold Conditions”).

The PRA and the FCA have their own sets of Threshold Conditions and, as dual-regulated firms, the managing agents must comply with both. The Threshold Conditions relate to matters including the adequacy of the firm’s financial and other resources and whether a firm is a fit and proper person to conduct its regulated activities, having regard to all the circumstances (including whether the firm’s affairs are conducted soundly and prudently).

When granted, a Part 4A Permission will specify: (i) a description of the activities the managing agent can carry on, including any limitations on the scope of the permission; (ii) the specified investments to which the permission relates; and (iii) requirements imposed in relation to the permission to require the managing agent to take, or to refrain from taking, specified action. These requirements may relate to a range of matters, including the scope of a managing agent’s business, capital, liquidity and interactions with affiliates. Once authorized, in addition to continuing to meet the Threshold Conditions, managing agents must comply with the requirements of the PRA Rulebook and the FCA Handbook which apply to them.

Additionally, a managing agent needs the permission of Lloyd’s to manage a syndicate.

A managing agent must also obtain prior approval from the PRA or the FCA (depending on the function in question) for any individual who carries on one or more specified “controlled functions,” such as executive or non-executive directors and persons responsible for risk management, internal audit or compliance. The controlled functions of managing agents specified by the PRA and the FCA are known as senior management functions (“SMFs”). The relevant regulator will only approve an individual if it is satisfied that such individual is “fit and proper” to perform the SMF in question, including by reference to the person’s honesty, integrity and reputation, competence and capability for the roles that the person is to assume in the firm and his or her financial soundness. The PRA and/or the FCA’s assessment of fitness and propriety often includes an interview of the candidate to perform a SMF.

The managing agents must carry out ongoing assessment of fitness and propriety in relation to all SMF holders. Individuals in SMFs are subject to a duty of responsibility in accordance with FSMA and can be held accountable if they fail to take “reasonable steps” to prevent regulatory breaches. Each SMF holder will have a statement of responsibilities showing what they are responsible for within the business. These responsibilities will be set out alongside reporting lines in a “Responsibilities Map” which is available to the regulators.

Individuals who do not hold SMFs but whose role means that they have the potential to cause harm to either the relevant managing agent or its customers must be certified by the managing agent in question as fit

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and proper to perform their role. Such roles are “Certification Functions” and include those functions which are considered to be Key Functions under the Solvency II Directive.

All staff in each of the managing agents, with the exclusion of those who are in roles such as catering or security (where they cannot pose a risk to the business or its customers), must comply with individual conduct rules. SMF holders must comply with additional conduct rules, relating to regulatory objectives.

Prudential and capital requirements

In summary, there are three parts to the “chain of security” that underpins the capital structure of Lloyd’s:

(i)

Syndicate level assets: The insurance premiums which are collected by members and held in a premium trust fund for the benefit of policyholders whose contracts are underwritten by the syndicate. These monies are the first resource used for paying claims made by the members’ policyholders from that syndicate.

(ii)

Funds at Lloyd’s: Each member must provide capital to support its underwriting at Lloyd’s. This capital is held in trust as a buffer to back up each member’s underwriting liabilities in each syndicate in which it is a member. The amount of capital to be provided by each member is determined by reference to the rules on the Solvency Capital Requirement (“SCR”) contained in the Solvency II Firms section of the PRA Rulebook, which apply to Lloyd’s and to its managing agents. Lloyd’s requires managing agents to determine the SCR on an ultimate basis (“uSCR”) for each syndicate they manage (described in greater detail below). Lloyd’s then applies an “Economic Capital Uplift” to each uSCR and the resulting figure is used to calculate each member’s capital resources requirement in proportion to its share of each syndicate of which it is a member.

(iii)

Mutual assets (Central Fund and callable layer): Members make annual contributions to the Central Fund which can be used to pay out in relation to the claims against any member who fails to meet its insurance liabilities in full. In addition, this is supplemented by a “callable layer” of up to 3% of members’ overall premium limits which Lloyd’s can call upon to meet claims.

When calibrating the SCR, Lloyd’s is required to include, in addition to the risks impacting its members, all quantifiable risks to which Lloyd’s itself is exposed, including risks to its central assets and central liabilities. Lloyd’s and its managing agents must also comply with requirements to conduct own risk and solvency assessments (“ORSA”) and to report, as set out in, respectively, the Conditions Governing Business and the Reporting parts of the Solvency II Firms section of the PRA Rulebook.

As dual-regulated firms in their own right, managing agents are under an obligation to manage the syndicate assets and the insurance business carried on by members of the syndicate in accordance with the Solvency II Firms section of the PRA Rulebook. This requires managing agents to ensure that the financial resources for each syndicate they manage and the capital resources at syndicate level are adequate, and that they establish and maintain systems and controls for the management of prudential, credit, market, operational and insurance risks for each syndicate.

Managing agents must calculate capital resources at syndicate level under the rules in the Solvency II Firms section of the PRA Rulebook and, in particular, must calculate an SCR for each syndicate (which captures the risks that will emerge over the next 12 months) and a uSCR (to capture potential adverse developments which may arise until all liabilities have been paid). The SCR and uSCR take into account the risks, controls and financial resources available to each syndicate, and are notified to Lloyd’s periodically.

Managing agents are also subject to their own regulatory capital requirements, comprising both a minimum qualifying capital requirement and minimum net asset requirement.

Conduct of Business

The FCA’s conduct of business requirements for managing agents can be found in the Insurance: Conduct of Business Sourcebook of the FCA Handbook (“ICOBS”). These rules regulate the day-to-day conduct of business standards to be observed by managing agents involved in insurance mediation activities and/or the activity of managing the underwriting capacity of a Lloyd’s syndicate (these are supplemented by Lloyd’s own

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rules, including certain prescribed minimum standards in respect of the management of conduct risk and complaints). Although the scope and range of obligations imposed by the ICOBS rules vary according to the scope of the firm’s business and the nature of its clients, generally the rules include the need to provide clients with information about the firm, meet certain standards of product disclosure, ensure that promotional materials are clear, fair and not misleading, assess suitability when advising on certain products, manage conflicts of interest, report appropriately to clients and provide certain protections in relation to client assets. The rules in ICOBS were amended with effect from October 1, 2018 to implement Directive 2016/97/EU (the “Insurance Distribution Directive”). The key changes brought about by the Insurance Distribution Directive include the introduction of: (i) an overarching requirement to act in a customer’s best interest; (ii) additional requirements to ensure that individuals who sell insurance are fit and proper (including new continuing professional development standards); (iii) a requirement for distributors to have in place product governance processes to ensure that policies are designed for their target audience; and (iv) information disclosure requirements providing for the delivery of simple, standardized policy summary documentation to retail customers. In addition, the Insurance Distribution Directive removed introducing as a regulated activity.

The FCA’s conduct of business requirements also apply to the U.K. operations of AWAC Europe.

Customer complaints and compensation

Lloyd’s itself and managing agents are under the compulsory jurisdiction of the Financial Ombudsman Service (“FOS”) which has been set up under FSMA. Authorized firms must have appropriate complaints handling procedures but, where these are exhausted, the FOS provides for dispute resolution in respect of complaints brought by eligible complainants.

The FOS is available to eligible complainants in addition to their right to bring a claim in the courts. If the FOS determines a dispute in favor of a complainant, it has the power to order a firm to pay compensation for any loss or damage it caused to the complainant, or to direct a firm to take such steps in relation to the complainant as the FOS considers just and appropriate, irrespective of whether a similar award could be made by a court. The FOS is funded by levies and case fees payable by firms covered by the FOS.

The Financial Services Compensation Scheme (“FSCS”) is established under FSMA and provides compensation to certain categories of customers who suffer losses as a consequence of the inability of a regulated firm to meet its liabilities arising from claims made in connection with regulated activities. The FSCS is funded by means of levies on all of its participating financial services firms, including Lloyd’s.

Money laundering and other financial crime

All FSMA authorized firms are required to undertake certain administrative procedures and checks, which are designed to prevent money laundering. The FCA Handbook contains rules which require firms to take reasonable care to establish and maintain effective systems and controls for countering the risk that the firm might be used to further financial crime. For these purposes, financial crime includes any offence involving fraud or dishonesty, misconduct in, or misuse of information relating to, a financial market or handling the proceeds of crime, as well as bribery and corruption offences. One of the FCA’s statutory objectives is to protect and enhance the integrity of the U.K. financial system which includes, among other things, reducing the opportunity for the U.K. financial system to be used for purposes connected with financial crime.

Qualifying parent undertaking

The PRA and the FCA have the power, in certain circumstances, to give directions to certain “qualifying parent undertakings” of U.K. authorized firms even where those parent undertakings are not themselves regulated, provided that the parent undertaking is incorporated in the United Kingdom or has a place of business in the United Kingdom. This power of direction allows the PRA or the FCA to direct the parent to take or refrain from taking specified action or to remedy past actions in prescribed circumstances.

Change of control of authorized firms

Under section 178 of FSMA, if a person intends to acquire or increase “control” over a PRA-authorized firm (including a Lloyd’s managing agent), it must first notify and get prior approval from the PRA before

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becoming a “controller” or increasing its level of control above certain thresholds. A person must also notify the PRA when the transaction which results in this acquisition or increase of control takes place.

A proposed “controller” for the purposes of the change of control regime is any natural or legal person or such persons “acting in concert” who decides to acquire or increase, directly or indirectly, his, her or its control over a U.K. authorized firm.

“Control” over a PRA authorized firm is acquired if the acquirer:

•

holds 10% or more of the shares or voting rights in that company or in its (direct or indirect) parent undertaking; or

•

is able to exercise significant influence over the management of the firm by virtue of the acquirer’s shares or voting power in the company or its (direct or indirect) parent undertaking.

Increases of control of a PRA authorized firm require the consent of the PRA where they reach the thresholds of 20%, 30% and 50% of the shares or voting power in the firm or its parent. Reducing or proposing to reduce control below the relevant threshold also gives rise to an obligation to notify the PRA.

Breach of the notification and approval regime is a criminal offence.

The approval of Lloyd’s is also required in relation to the change of control of a Lloyd’s managing agent or member. Broadly, Lloyd’s applies the same tests in relation to control as are set out in FSMA and, in practice, where the application relates to a managing agent, coordinates its approval process with that of the PRA.

Other Relevant Issues for the Insurance Sector in the United Kingdom

Passporting

Firms authorized in an European Economic Area (“EEA”) state to carry on activities regulated under one of the relevant directives emanating from the European Union (the “Single Market directives”) are entitled to carry on those regulated activities in any other EEA state without needing to become directly authorized by the regulator of the host EEA state. This is known as “passporting,” and can involve either the setting up of an establishment in the host EEA state or the provision of cross-border services. The Solvency II Directive is, for example, a Single Market directive. Whilst the United Kingdom was part of the EEA, Brit Syndicates Limited had permission from the PRA to exercise passporting rights out of the United Kingdom and into other EEA states.

The United Kingdom left the European Union at 23:00 (Greenwich Mean Time) on January 31, 2020. Prior to this, the European Union (Withdrawal Agreement) Act 2020 (the “Withdrawal Act”) entered into law in the United Kingdom on January 23, 2020. The Withdrawal Act provided for an “implementation period,” during which time existing arrangements between the United Kingdom and European Union would continue to apply, until December 31, 2020 (and, during that period, U.K. firms were able to continue to benefit from their passporting permissions). Following December 31, 2020, U.K. firms are no longer able to exercise passporting rights. To enable clients with EEA business to continue to access the Lloyd’s market, Lloyd’s has established a subsidiary in Belgium, Lloyd’s Insurance Company S.A., (“Lloyd’s Europe”) which is authorized by the National Bank of Belgium (“NBB”), regulated by the NBB and the Financial Services and Markets Authority and benefits from passporting permissions in all EEA states. Lloyd’s Europe can accept risks and issue policies via Lloyd’s Europe registered brokers, service companies and coverholders. All Lloyd’s Europe policies are then 100% reinsured back to Lloyd’s syndicates (each risk bound by Lloyd’s Europe is allocated to a relevant syndicate), meaning that clients will benefit from Lloyd’s chain of security (as described above). This structure enables the members of Syndicate 2987, Syndicate 1218 and Syndicate 2232 to continue to have an interest in EEA business (albeit as reinsurers rather than direct insurers). For completeness, we note that all of Lloyd’s historic general insurance EEA business was transferred from Lloyd’s to Lloyd’s Europe with effect from 30 December 2020 pursuant to Part VII of FSMA (including any EEA business of the members of the members of Syndicate 2987, Syndicate 1218 and Syndicate 2232 — such business was subsequently 100% reinsured by the members of the relevant syndicate).

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With regard to EEA firms (such as AWAC Europe) carrying on business in the United Kingdom, HM Treasury has legislated for a temporary permissions regime (“TPR”) which took effect from the end of the implementation period referred to above. The aim of the TPR is to allow firms that wish to continue carrying on business in the U.K. in the longer term to operate in the U.K. for a limited period after the passporting regime ended while they seek full authorisation from U.K. regulators. Under the TPR, a firm that is authorized to carry on regulated activities in the U.K. on a freedom of establishment or freedom of services basis can obtain a deemed permission to carry on those activities for a maximum of three years from the end of the implementation period, subject to HM Treasury’s power to extend the duration of the regime by increments of twelve months. AWAC Europe benefits from the TPR and currently intends to submit an application to establish a third country branch in the U.K. in late 2022.

Ogden Tables

Our insurance business in the United Kingdom includes insurance of liability for personal injury. Where a personal injury claim is determined or settled with a lump sum payment, the payment is calculated in accordance with the “Ogden Tables.” The Ogden Tables contain a discount rate that is set by the U.K. government and is applied when calculating the present value of loss of earnings for claims settlement purposes. A change in the discount rate used in the Ogden Tables impacts all relevant claims settled after that date, regardless of whether the insurance to which the claim relates was priced on that basis or not (or occurred after that date or not). A reduction in the Ogden discount rate increases lump sum payments to personal injury claimants, and in consequence the amount of reserves required to be held by insurers in relation to outstanding claims. The Ogden discount rate was reduced from 2.5% to −0.75% with effect from March 20, 2017, resulting in large increases in the amount of insurance reserves held for some claims. The U.K. government, following a review of the Ogden discount rate (in accordance with the Damages Act 1996, as amended by the Civil Liability Act 2018) announced an increase to the Ogden discount rate in England and Wales to -0.25% on July 15, 2019.

Data protection

The United Kingdom and the European Union are subject to data protection laws, which regulate the obtaining and use of personal data relating to living individuals. As a result of leaving the EU, the U.K.’s data protection laws are the UK General Data Protection Regulation (“UK GDPR”), supplemented by the Data Protection Act 2018. The UK GDPR reflects the EU’s GDPR (“EU GDPR”), which applies across the EEA (also supplemented by national data protection laws), which has applied since 25 May 2018. The UK GDPR or EU GDPR (as applicable) applies to everyone working in Fairfax’s businesses in the EEA and the U.K., as well as Fairfax’s businesses outside the EEA or U.K. that provide services to or monitor individuals (including customers) in the EEA or the U.K. (as applicable) as a result of the extraterritorial application of these laws. The UK GDPR and EU GDPR require, among other things, businesses to perform data protection impact assessments, and allow individuals (data subjects) to request access to their data and the erasure of their data and data portability subject to certain restrictions. They restrict companies’ ability to transfer personal data from inside the EEA or the U.K. to outside the EEA or U.K. and a recent European Court of Justice decision (Schrems II) invalidated one of the primary methods for transferring personal data to the United States and placed conditions on the use of the main alternative export solution, the Standard Contractual Clauses. In July 2021, the U.K. was granted “adequacy” by the EU’s European Commission, which enables companies to transfer personal data from the EEA to the U.K. without using the Standard Contractual Clauses or other additional export methods. National data protection authorities have increased enforcement powers under the EU GDPR and UK GDPR (which provide for maximum fines for non-compliance of the higher of €20 million/£17.5 million and four per cent of an organization’s worldwide turnover). In recent years, enforcement has been particularly focused on issues such as the management of personal data breaches, the sending of unsolicited marketing materials (especially in the U.K.), and the retention of data for excessive periods of time. The concept of accountability is at the heart of the rules, meaning that companies need to be able to demonstrate that they have implemented a compliance program that reflects and enables them to meet the legal requirements for processing of personal data in the EEA and/or the U.K. On September 10, 2021, the U.K. government announced its proposals to reform the U.K.’s data protection laws which, depending on the outcome of the consultation, could challenge the U.K.’s “adequacy” designation and make it more difficult for companies to transfer personal data from the EEA to the U.K.

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Business interruption test case

Our insurance business in the United Kingdom includes insurance of business interruption risks. In May 2020, the FCA announced its intention to bring a test case in the High Court of England and Wales to seek legal clarity about the meaning and effect of selected business interruption insurance policy wordings in the context of COVID-19 claims. The FCA provided a representative sample of business interruption policies to the High Court and asked it to determine whether on the basis of certain agreed and assumed facts: (a) the policies provide cover in principle; and (b) the policyholders of the policies can establish the necessary causal link (as a matter of the application of the law and the wording of the policies) between the assumed losses sustained by policyholders and any relevant peril, event or circumstance that is covered by relevant terms in the policies. The hearing took place in late July 2020 and judgment was handed down at first instance on September 15, 2020 (FCA v Arch Insurance (UK) Ltd and others [2020] EWHC 244).

In January 2021, the UK Supreme Court handed down judgment on appeal which was ‘leapfrogged’ from the decision of the High Court (FCA v Arch Insurance (UK) Ltd and others [2021] UKSC 1). The judgment is legally binding on the insurers that were parties to the case in respect of interpreting the business interruption policy wordings considered. The decision provides persuasive guidance for the interpretation of similar policy wordings and claims that can be taken into account by the Court, the FOS and the FCA. The FCA has also introduced new guidance setting out its expectation that insurers should apply the judgment in assessing or reassessing all outstanding or rejected claims and complaints that may be affected by the test case (except those that have been referred to the FOS). The FCA has estimated that the judgment affects around 370,000 policyholders who are able to recover losses relating to business interruption due to COVID-19, but the implications of the decision go beyond the pandemic and will impact claims that have nothing to do with the events of the past few months. The Arch judgment has changed the law in respect of various terms applied in business interruption policies such as trends clauses with the effect that higher settlement figures should be anticipated.

Bermuda

General

Our insurance and reinsurance business in Bermuda is subject to the Bermuda Insurance Act 1978 (the “Bermuda Insurance Act”). The Bermuda Insurance Act imposes solvency and liquidity standards as well as auditing and reporting requirements on Bermuda insurers and reinsurers. It also empowers the Bermuda Monetary Authority (“BMA”) to supervise, investigate and intervene in the affairs of these entities. There are a number of remedial actions available to the BMA in order to protect the public interest if the BMA determines that a Bermuda insurer or reinsurer may become insolvent or that a breach of the Bermuda Insurance Act or of any of the conditions of registration on a Bermuda insurer or reinsurer has occurred or is about to occur.

In addition to maintaining a principal office in Bermuda and appointing specified officers, the summary below comprises the material aspects of the insurance regulatory framework in Bermuda with which our Bermuda insurer and reinsurer must comply.

Solvency and Capital Standards

Our Bermuda insurer and reinsurer must maintain a minimum solvency margin and hold available statutory economic capital and surplus equal to or in excess of their “enhanced capital requirement” and “target capital level” as determined by the BMA under the Bermuda Solvency Capital Requirement model (the “BSCR model”). The BSCR model is a risk-based capital model that establishes an enhanced capital requirement and total capital level by taking into account risk characteristics specific to an insurer’s or reinsurer’s business. The target capital level is measured as 120% of the enhanced capital requirements. Our Bermuda insurer and reinsurer is also required to maintain a minimum solvency margin that is equal to the greatest of:

(i)

$100,000,000;

(ii)

50% of net premiums written;

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(iii)

15% of net losses and loss expense reserves; and

(iv)

25% of the insurer’s and reinsurer’s enhanced capital requirement.

Eligible Capital and Liquidity

Our Bermuda insurer and reinsurer is required to disclose the makeup of its capital under a “three-tiered capital system”. Under this system, capital instruments are classified as either “basic” or “ancillary” capital, and are further classified into one of three tiers based on certain prescribed “loss absorbency” characteristics. The minimum and maximum thresholds of tier 1, 2 and 3 capital that may be used to support a company’s minimum solvency margin, enhanced capital requirement and target capital level are determined in accordance with the BMA’s rules. In addition, minimum liquidity must be maintained whereby the value of the applicable insurer’s and reinsurer’s relevant assets is not less than 75% of the amount of its relevant liabilities.

Dividends

Our Bermuda insurer and reinsurer is prohibited from declaring or paying dividends during any financial year if the insurer or reinsurer is, or would after such dividend is paid be, in breach of its minimum solvency margin, minimum liquidity ratio or enhanced capital requirements. Our material Bermuda insurer and reinsurer must also receive BMA approval prior to declaring or paying, within any financial year, dividends in respect of more than 25% of its total statutory capital and surplus or reducing its total statutory capital by 15% or more. Additionally, under the Companies Act 1981 of Bermuda, no Bermuda company may pay a dividend if such company has reasonable grounds for believing that it is, or would after such dividend payment be, unable to pay its liabilities as they become due, or that the realizable value of its assets would thereby be less than its liabilities.

Code of Conduct

Our Bermuda insurer and reinsurer must comply with the BMA’s Insurance Code of Conduct, which prescribes the duties, standards, procedures and sound business principles with which all companies registered under the Bermuda Insurance Act must comply.

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DESCRIPTION OF THE NOTES

As used under this heading “Description of the Notes”, the terms “Fairfax”, “Company”, “we”, “us” and “our” refer only to Fairfax Financial Holdings Limited, and not its subsidiaries. The Company issued the Initial Notes under an indenture, dated as of December 1, 1993, as supplemented and amended by the first supplemental indenture dated May 9, 2011 and the third supplemental indenture (the “Third Supplemental Indenture”), dated as of February 26, 2021 (collectively, the “Indenture”), among the Company, The Bank of New York Mellon, as successor U.S. trustee (the “United States trustee” or the “trustee”), and BNY Trust Company of Canada (as successor trustee to CIBC Mellon Trust Company), as successor Canadian trustee (the “Canadian trustee” and, together with the United States trustee, the “trustees”) in a private transaction that was not subject to the registration requirements of the Securities Act or the requirement to qualify the Initial Notes by prospectus or otherwise under Canadian securities legislation. The Company has agreed to offer to exchange the Initial Notes for a new issue of substantially identical debt securities (as previously defined as the Exchange Notes) registered under the Securities Act. The issuance of the Exchange Notes in this offering (together with any Initial Notes that are not tendered and accepted for purchase) will be limited to $600 million. The Exchange Notes, together with any Initial Notes that remain outstanding after the closing of the Exchange Offer, are referred to herein as the “Notes”.

The Indenture provides that, in addition to the Notes, securities of other series may be issued under the Indenture without limitation as to aggregate principal amount. The securities of other series may have such terms and provisions not inconsistent with the Indenture as the Company may determine from time to time. The securities of any series issued under the Indenture, including the Notes, are referred to as “securities.”

The Notes bear interest from the date of issuance at the rate of 3.375% per annum, and will mature on March 3, 2031. Interest will be payable in semi-annual installments in arrears on March 3 and September 3 each year (each, an “Interest Payment Date”) to the persons in whose names the Notes are registered at the close of business on the preceding February 17 and August 17, respectively (whether or not a business day) (the “Regular Record Date”).

Interest is calculated on the basis of a 360-day year consisting of twelve 30-day months. Principal of and interest on the Notes is payable in such coin or currency of the United States of America as at the time of payment is legal tender for the payment of public and private debts.

If any Interest Payment Date, maturity date or Redemption Date (as defined below) of a Note falls on a day that is not a business day, the required payment of principal, premium, if any, and interest will be made on the next succeeding business day as if made on the date that the payment was due and no interest will accrue on that payment for such period from and after that Interest Payment Date, maturity date or Redemption Date, as the case may be, to the date of that payment on the next succeeding business day. The term “business day” means any day, other than a Saturday or Sunday, which is not a day on which banking institutions in the City of New York are authorized or required by law or executive order to close.

The Notes are not redeemable at the option of the holder prior to maturity and are not subject to any sinking fund.

The following summary of certain provisions of the Indenture does not purport to be complete and is subject to, and qualified in its entirety by reference to, all of the provisions of the Indenture. Whenever reference is made to particular sections of the Indenture or terms that are defined therein, such sections or defined terms are incorporated herein by reference as a part of such summaries, which are qualified in their entirety by such reference. The Indenture is subject to the provisions of the Canada Business Corporations Act and accordingly is exempt from certain provisions of the U.S. Trust Indenture Act of 1939, as amended (the “Trust Indenture Act”), pursuant to Rule 4d-9 thereunder. References to accounting terms in the Indenture and in this summary, unless otherwise defined, have the meanings assigned to them in accordance with IFRS.

General

The Notes are the Company’s direct, unsecured obligations and rank equally and ratably with all of the Company’s other unsecured and unsubordinated indebtedness from time to time outstanding. The Notes rank among themselves equally and ratably without preference or priority. The Notes would be structurally

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subordinated to all obligations of the Company’s subsidiaries. The Notes would be effectively subordinated to any future secured indebtedness of the Company, to the extent of the assets securing such indebtedness.

As of June 30, 2021, the Company had approximately $6.2 billion principal amount of total outstanding indebtedness, none of which is secured, and the Company’s subsidiaries had approximately $2.7 billion principal amount of total outstanding indebtedness, all of which would be structurally senior to the Notes.

The Indenture permits the Company from time to time, without notice to or the consent of the holders of any series of securities issued under the Indenture, to create and issue further securities of the same series as the Notes, ranking pari passu with the Notes in all respects and having the same terms as the Notes (except for the issue date, issue price and initial Interest Payment Date following the issue date of such further notes) and so that such further notes shall be consolidated and form a single series with, and shall have the same terms as to status, redemption or otherwise as, the Notes; provided that such further notes will not be issued with the same CUSIP and/or ISIN numbers as the Notes unless such further notes are fungible with the Notes for U.S. federal income tax purposes.

The Notes are issuable in minimum denominations of $2,000 and integral multiples of $1,000 in excess thereof.

The Indenture does not contain any provisions that would limit the Company’s ability to incur indebtedness or that would afford holders of Notes protection in the event of a highly leveraged or similar transaction involving the Company.

Optional Redemption

The Notes are redeemable at any time prior to December 3, 2030 (the “Par Call Date”), at the option of the Company, in whole at any time or in part from time to time, on not less than 15 days’ nor more than 60 days’ prior notice to each registered holder, upon payment of a redemption price equal to the greater of:

(1)

100% of the principal amount of the Notes to be redeemed; or

(2)

the sum of the present values of the remaining scheduled payments of principal of and interest on such Notes that would be due if the Notes matured on the Par Call Date (not including any portion of such payments of interest accrued as of the Redemption Date) discounted to the Redemption Date on a semi-annual basis (assuming a 360-day year consisting of twelve 30-day months) at the Treasury Rate plus 30 basis points (the “Make Whole Amount”),

plus, in each case, accrued and unpaid interest to, but excluding, the Redemption Date. The Company will pay any interest due on an Interest Payment Date that occurs on or prior to a Redemption Date to the registered holders of the Notes as of the close of business on the Regular Record Date immediately preceding that Interest Payment Date.

The Notes are redeemable at any time on or after the Par Call Date, at the option of the Company, in whole at any time or in part from time to time, on not less than 15 days’ nor more than 60 days’ prior notice to each registered holder, upon payment of a redemption price equal to par, together with accrued and unpaid interest to the Redemption Date. Unless the Company defaults in payment of the redemption price, on and after the applicable Redemption Date, interest will cease to accrue on the Notes or portions thereof called for redemption.

For purposes of determining the Make Whole Amount, the following definitions apply:

“Comparable Treasury Issue” means the United States Treasury security or securities selected by the Quotation Agent as having an actual or interpolated maturity comparable to the remaining term of the Notes from the applicable Redemption Date to the Par Call Date (the “Remaining Life”) of the Notes to be redeemed that would be utilized at the time of selection, and in accordance with customary financial practice, in pricing new issues of corporate debt securities of comparable maturity to the Remaining Life of the Notes to be redeemed.

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such Reference Treasury Dealer Quotations or (2) if the Quotation Agent obtains fewer than five Reference Treasury Dealer Quotations, the average of any such Reference Treasury Dealer Quotations.

“Quotation Agent” means the Reference Treasury Dealer appointed by the Company.

“Redemption Date” means any date fixed for redemption of Notes.

“Reference Treasury Dealer” means (i) BofA Securities, Inc., J.P. Morgan Securities LLC and Citigroup Global Markets Inc. (or their respective affiliates that are primary treasury dealers) and their successors; provided, however, that if any of the foregoing shall cease to be a primary United States Government securities dealer in the United States of America, the Company will substitute therefor another primary treasury dealer, and (ii) any other primary treasury dealer selected by the Company.

“Reference Treasury Dealer Quotation” means, with respect to the Reference Treasury Dealer and any Redemption Date, the average, as determined by the Company, of the bid and asked prices for the Comparable Treasury Issue (expressed, in each case, as a percentage of its principal amount) quoted in writing to the Quotation Agent by such Reference Treasury Dealer at 5:00 p.m., New York City time, on the third business day preceding such Redemption Date.

“Treasury Rate” means, with respect to any Redemption Date, the rate per annum equal to the semi-annual equivalent or interpolated (on a day-count basis) yield to maturity of the Comparable Treasury Issue, calculated using a price for the Comparable Treasury Issue (expressed as a percentage of its principal amount) equal to the Comparable Treasury Price for such Redemption Date. The Treasury Rate will be calculated on the third business day preceding such Redemption Date.

The Notes are also subject to redemption prior to maturity if certain changes in Canadian tax law occur. If such changes occur, the Notes may be redeemed at a redemption price of 100% of their principal amount, plus any interest accrued but not paid to but excluding the Redemption Date and any additional amounts due and payable on the Notes up to but excluding the Redemption Date. See “— Redemption for Tax Reasons.”

Payment of Additional Amounts

All payments made by the Company under or with respect to the Notes will be made free and clear of, and without withholding or deduction for or on account of, any present or future tax, duty, levy, impost, assessment or other governmental charge imposed or levied by or on behalf of the Government of Canada or of any province or territory thereof or by any authority or agency therein or thereof having power to tax (hereinafter “Taxes”), unless the Company is required to withhold or deduct Taxes by law or by the interpretation or administration thereof. If the Company is so required to withhold or deduct any amount for or on account of Taxes from any payment made under or with respect to the Notes, the Company will pay as interest such additional amounts (“Additional Amounts”) as may be necessary so that the net amount received by each holder of such Notes or the beneficial owner thereof (including Additional Amounts) after such withholding or deduction will not be less than the amount such holder or beneficial owner would have received if such Taxes had not been withheld or deducted; provided that no Additional Amounts will be payable with respect to: (a) any payment made to a holder of the Notes or beneficial owner who is liable for such Taxes in respect of such Notes (i) by reason of such holder or beneficial owner, or any other person entitled to payments on the Notes, being a person with which the Company does not deal at arm’s length (within the meaning of the Income Tax Act (Canada) (the “Canadian Tax Act”)), (ii) by reason of such holder or beneficial owner being a “specified shareholder” of the Company or not dealing at arm’s length with a “specified shareholder” of the Company (as defined in subsection 18(5) of the Canadian Tax Act), (iii) by reason of the existence of any present or former connection between such holder or beneficial owner (or between a fiduciary, settlor, beneficiary, member or shareholder of, or possessor of power over, such holder or beneficial owner, if such holder or beneficial owner is an estate, trust, partnership, limited liability company or corporation) and Canada or any province or territory thereof or therein or agency thereof or therein other than the mere acquisition, holding, use or ownership or deemed holding, use or ownership, or receiving payments or enforcing any rights in respect of such Notes as a non-resident or deemed non-resident of Canada or any province or territory thereof or therein or agency thereof or therein, or (iv) by reason of such holder or beneficial owner’s failure to comply with any certification, identification, documentation or other reporting requirements if compliance is required by law, regulation, administrative practice or an applicable treaty as a

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pre-condition to exemption from, or a reduction in the rate of deduction or withholding of, such Taxes, in each case, to the extent such holder or beneficial holder is legally entitled to such exemption or reduction; (b) any estate, inheritance, gift, sales, transfer, excise or personal property tax or any similar Taxes; (c) any Notes presented for payment more than 15 days after the date on which such payment or such Notes became due and payable or the date on which payment thereof is duly provided for, whichever is later (except to the extent that the holder would have been entitled to such Additional Amounts had the Notes been presented on the last day of such 15-day period); (d) any withholding or deduction imposed on a payment to a holder or beneficial owner pursuant to Sections 1471 to 1474 of the U.S. Internal Revenue Code of 1986, as amended or any successor version thereof, any agreements entered into pursuant to current Section 1471(b)(1) of the Code, and any fiscal or regulatory legislation, rules or official guidance, adopted pursuant to any intergovernmental agreement among governmental authorities entered into in connection with the implementation of the foregoing, and including for greater certainty, Part XVIII and Part XIX of the Canadian Tax Act (“FATCA”), or any Taxes or penalties that arise from the holder or beneficial owner’s failure to properly comply with its obligations with respect to FATCA or the Canada United States Enhanced Tax Information Exchange Agreement Implementation Act (Canada); (e) any Taxes which are payable otherwise than by withholding or deduction from any payment made under or with respect to the Notes or (f) any combination of the foregoing clauses (a) to (e); nor will such Additional Amounts be paid with respect to any payment on any Note to a holder or beneficial owner who is a fiduciary or partnership or, other than the sole beneficial owner of such Note, to the extent that a beneficiary or settlor with respect to such fiduciary, or a member of such partnership or a beneficial owner thereof would not have been entitled to receive a payment of such Additional Amounts had such beneficiary, settlor, member or beneficial owner received directly its beneficial or distributive share of such payment (collectively, “Excluded Taxes”). The Company will also (a) make such withholding or deduction and (b) remit the full amount deducted or withheld to the relevant authority in accordance with applicable law. Upon the written request of the trustee or a holder of Notes, the Company will furnish, as soon as reasonably practicable, to the trustee or such holder of Notes, as applicable, certified copies of tax receipts evidencing such payment by the Company. The Company will indemnify and hold harmless each holder of Notes and any beneficial owner thereof and, upon written request of any such holder or beneficial owner, reimburse such holder or beneficial owner for the amount of (i) any such Taxes (other than Excluded Taxes) so levied or imposed and paid by such holder or beneficial owner as a result of any failure of the Company to withhold, deduct or remit to the relevant tax authority, on a timely basis, the full amounts required under applicable law; and (ii) any such Taxes (other than Excluded Taxes) so levied or imposed with respect to any reimbursement under the foregoing clause (i), so that the net amount received by such holder or beneficial owner after such reimbursement would not be less than the net amount such holder or beneficial owner would have received if such Taxes (other than Excluded Taxes) on such reimbursement had not been imposed.

Whenever in the Indenture there is mentioned, in any context, the payment of principal (and premium, if any), redemption price, interest or any other amount payable under or with respect to the Notes, such mention shall be deemed to include mention of the payment of Additional Amounts to the extent that, in such context, Additional Amounts are, were or would be payable in respect thereof.

Redemption for Tax Reasons

In the event that the Company has become or would become obligated to pay, on the next date on which any amount would be payable under or with respect to the Notes, any Additional Amounts as a result of a change in the laws (including any regulations promulgated thereunder) or treaties of Canada (or any political subdivision or taxing authority thereof or therein), or any change in any official position regarding the application or interpretation of such laws, regulations or treaties, which change is announced and becomes effective on or after the date of issuance of the Notes, then the Company may at any time at the Company’s option redeem the Notes, in whole, but not in part, at a redemption price equal to 100% of their principal amount, plus any interest accrued but not paid to but excluding the Redemption Date and any additional amounts due and payable on the Notes up to but excluding the Redemption Date.

If the Company exercises its option to redeem the Notes, the Company will deliver to the trustee a certificate signed by an authorized officer stating that the Company is entitled to redeem the Notes to the effect that the circumstances described above exist.

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Selection and Notice of Redemption

In the event that the Company chooses to redeem less than all of the Notes, selection of the Notes for redemption will be made by the trustee in compliance with the requirements of the principal national securities exchange, if any, on which the Notes are listed, or, if the Notes are not so listed, on a pro rata basis, by lot or by such other method in accordance with the depositary’s procedures.

No Notes of a principal amount of $2,000 or less shall be redeemed in part. Notice of redemption of Notes held in the form of Definitive Certificates (as defined below) will be mailed by first-class mail at least 15 days but not more than 60 days before the Redemption Date to each holder of Notes to be redeemed at its registered address. Notice of redemption of Notes held in the form of global certificates will be given to DTC in accordance with its applicable procedures at least 15 days but not more than 60 days before the Redemption Date. If any Note is to be redeemed in part only, the notice of redemption that relates to such Note shall state the portion of the principal amount thereof to be redeemed. A new Note in principal amount equal to the unredeemed portion thereof will be issued in the name of the holder thereof upon cancellation of the original Note.

On and after the Redemption Date, interest will cease to accrue on Notes or portions thereof called for redemption as long as the Company has deposited with the paying agent funds in satisfaction of the applicable redemption price.

Certain Covenants

The Third Supplemental Indenture has amended the Indenture to eliminate and amend certain restrictive covenants of the Company. Such covenants will be automatically eliminated or amended effective as of the first date (the “Amendment Date”) on which there are no securities outstanding of any series created pursuant to the Indenture prior to the date of the Third Supplemental Indenture that are entitled to the benefit of such original covenants, including in respect of the limitation on liens on capital stock of restricted subsidiaries described below. The Third Supplemental Indenture also provides that if we grant any security interest to any collateral agent or trustee pursuant to such covenant in connection with any series created after the date of the Third Supplemental Indenture, such security interest shall be automatically released on the Amendment Date and any such collateral agent or trustee shall be authorized to take such further actions as we may reasonably request to give effect to such release.

Limitation on Liens on Capital Stock of Restricted Subsidiaries. Until the Amendment Date, the Indenture provides that the Company may not, and may not permit any subsidiary to, create, assume, incur or suffer to exist any lien, other than a purchase money lien, upon any capital stock, whether owned on the date of the Indenture or thereafter acquired, of any restricted subsidiary, to secure any obligation (other than the securities issued under the Indenture) of the Company, any subsidiary or any other person, without in any such case making effective provision whereby all of the outstanding securities issued under the Indenture shall be directly secured equally and ratably with such obligation; provided, however, that this restriction will not apply to (i) liens on the capital stock of any restricted subsidiary securing obligations outstanding from time to time under any bank credit facility, provided that the principal amount of all such obligations secured by liens on the capital stock of any restricted subsidiary, at the time of each incurrence of any portion of any such obligation, does not exceed 15% of the sum of (A) the Company’s consolidated shareholders’ equity at the end of the Company’s most recently completed fiscal quarter immediately preceding such incurrence for which financial statements are, or are required to be, available and (B) the aggregate principal amount of all obligations which are outstanding under any bank credit facility immediately after giving effect to such incurrence and which are secured by liens on the capital stock of a restricted subsidiary, and (ii) liens securing obligations from the Company to any wholly-owned restricted subsidiary or from any wholly-owned restricted subsidiary to the Company or any other wholly-owned restricted subsidiary. This provision will not restrict any other property of the Company or that of its subsidiaries.

The Indenture defines “lien” as any mortgage, pledge, hypothecation, lien, encumbrance, charge or security interest of any kind; “obligation” as indebtedness for money borrowed or indebtedness evidenced by a bond, note, debenture or other evidence of indebtedness; “purchase money lien” as (i) any mortgage, pledge, hypothecation, lien, encumbrance, charge or security interest of any kind upon any capital stock of any restricted subsidiary acquired after the date of the Indenture if such purchase money lien is for the purpose of

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financing, and does not exceed, the cost to the Company or any subsidiary of acquiring the capital stock of such restricted subsidiary and such financing is effected concurrently with, or within six months after, the date of such acquisition, and (ii) any extension, renewal or refinancing of any purchase money lien so long as the principal amount of obligations secured thereby shall not exceed the original principal amount of obligations so secured at the time of such extension, renewal or refinancing; “restricted subsidiary” as any subsidiary that is a licensed insurance company, other than any licensed insurance company that the Company’s board of directors, in good faith, determines is not, individually or together with any other licensed insurance company as to which a similar determination has been made, material to the business of the Company and its subsidiaries, considered as a whole; and “subsidiary” as a corporation or business trust, a majority of the outstanding voting stock of which is owned, directly or indirectly, by the Company or one or more other subsidiaries, or by the Company and one or more other subsidiaries. As of the date hereof, each of the Company’s licensed insurance company subsidiaries is a restricted subsidiary.

Waiver of Certain Covenants. The Company may omit in any particular instance to comply with any term, provision or condition of the covenants described above if the holders of at least a majority in principal amount of all outstanding Notes issued under the Indenture and then outstanding waive compliance in such instance with such term, provision or condition.

Amalgamation, Consolidation, Merger, Conveyance, Transfer or Lease. The Indenture provides that the Company shall not amalgamate or consolidate with or merge into any other corporation or convey, transfer or lease its properties and assets substantially as an entirety to any other person, unless, (i) the corporation formed by such consolidation or amalgamation or into which the Company is merged or the person which shall have acquired or leased such properties or assets (if other than the Company) shall be a corporation, partnership, company or trust organized and validly existing under the laws of Canada or any province thereof or the United States, any state thereof or the District of Columbia, and shall expressly assume by supplemental Indenture the Company’s obligation for the due and punctual payment of the principal of (and premium, if any, on) and interest on all the outstanding securities issued under the Indenture, all other amounts payable by the Company pursuant to the Indenture and the performance and observance of every covenant of the Indenture on the Company’s part to be performed or observed, (ii) immediately after giving effect to such transaction, no event of default or event that after notice or passage of time or both would be an event of default shall have occurred and be continuing and (iii) the Company has delivered to the trustee an officers’ certificate and an opinion of counsel, each stating that such amalgamation, consolidation, merger, conveyance, transfer or lease, and supplemental indenture (if any), comply with this covenant and that all conditions precedent provided for in the Indenture relating to such transaction have been complied with.

Available Information. So long as the Notes are “restricted securities” within the meaning of Rule 144 under the Securities Act (“Rule 144”), and the Company is not subject to the reporting requirements of the Exchange Act, the Company will furnish to any holder of Notes, or to any prospective purchaser designated by such a holder, upon the request of the holder, the business and financial information concerning the Company called for under paragraph (d)(4) of Rule 144A.

Events of Default

The following constitute events of default with respect to the Notes under the Indenture: (a) a default for 30 days in the payment of any interest on any Note; (b) a default in the payment of the principal of (or premium, if any, on) any Note when due; (c) a default in the performance, or breach, of any other covenant or warranty in the Indenture (other than a covenant or warranty included in the Indenture solely for the benefit of one or more series of securities other than the Notes) which default or breach continues for a period of 60 days after notice; (d) a default in the payment, at the stated maturity, of any outstanding indebtedness for money borrowed by the Company in excess of $10,000,000 and continuing after any applicable grace period, which default shall not have been cured or waived, or the acceleration of indebtedness for money borrowed by the Company outstanding under or evidenced by any single Indenture or instrument in excess of $10,000,000, if such indebtedness has not been discharged, or such acceleration has not been rescinded or annulled, within 10 days after written notice has been given by the trustee, or the holders of at least 25% in principal amount of the outstanding Notes, as provided in the Indenture; and (e) certain events of bankruptcy, insolvency or reorganization.

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Pursuant to the terms of the Third Supplemental Indenture, the indenture has been amended to replace references to “$10,000,000” in clause (d) of the above paragraph with references to “$100,000,000”, effective on the Amendment Date.

If an event of default relating to a default in payment of principal of (or premium, if any, on) or interest on the Notes, or to a default in the performance, or breach, of any other covenant or warranty of the Company applicable to the Notes but not applicable to all outstanding securities issued under the Indenture, or to a default in the payment, at stated maturity, of, or to the acceleration of, any indebtedness for money borrowed shall have occurred and be continuing, the trustee or the holders of not less than 25% in principal amount of the Notes then outstanding may then declare the principal of all Notes to be due and payable immediately. If an event of default relating to a default in the performance, or breach, of any other covenant or warranty in the Indenture applicable to all securities issued thereunder and then outstanding shall have occurred and be continuing, the trustee or the holders of not less than 25% in principal amount of all securities issued under the Indenture and then outstanding (treated as one class) may declare the principal amount of all the securities then outstanding to be due and payable immediately. If an event of default described in clause (e) above shall occur, other than with respect to one of the Company’s subsidiaries, the principal amount of all the securities will automatically, and without any action by the trustee or any holder, become immediately due and payable. In each case, the holders of a majority in principal amount of the outstanding Notes may under certain circumstances rescind and annul such declaration by written notice to the Company and the trustee. In the event of a declaration of acceleration because an event of default specified in clause (d) above has occurred and is continuing, such declaration of acceleration shall be automatically annulled if the indebtedness which is the subject of such event of default has been discharged or the holders thereof have rescinded their declaration of acceleration in respect of such indebtedness, and written notice of such discharge or rescission is given to the trustee by the Company and countersigned by the holders of such indebtedness or their representative, within 30 days after such declaration of acceleration in respect of the Notes, and no other event of default has occurred during such 30-day period which has not been cured or waived during such period.

The holders of not less than a majority in principal amount of the outstanding Notes, in the case of an event of default applicable to such series but not to all outstanding securities, or a majority in principal amount of the outstanding securities of all series, in the case of an event of default applicable to all outstanding securities, may waive any past default and its consequences, except a default in respect of the payment of the principal of (or premium, if any, on) or interest on any security or in respect of a covenant or provision of the Indenture which cannot be modified or amended without the consent of the holder of each outstanding security affected thereby.

The Indenture provides that the trustee shall be under no obligation to exercise any of the rights or powers vested in it by the Indenture at the request or direction of holders of securities unless such holders shall have offered to the trustee reasonable funding, security and indemnity against the costs, expenses and liabilities which might be incurred by the trustee in compliance with such request or direction. Subject to such provisions for the indemnification of the trustee, the holders of not less than a majority in principal amount of the securities of any series (with respect to any remedy, trust or power relating to any default in payment of principal (or premium, if any, on) or interest on the securities of such series or any default in the performance or breach of any other covenant or warranty of the Company applicable to the securities of such series but not applicable to all outstanding securities issued under the Indenture) or the holders of not less than a majority in principal amount of all securities issued under the Indenture and then outstanding (treated as one class) (with respect to any other remedy, trust or power) shall have the right to direct the time, method and place of conducting any proceeding for any remedy available to the trustee, or exercising any trust or power conferred on the trustee, with respect to such securities.

Discharge, Defeasance and Covenant Defeasance

The Company may discharge certain obligations to holders of Notes which have not already been delivered to the trustee for cancellation and which have either become due and payable or are by their terms due and payable within one year by irrevocably depositing with the trustee trust funds in an amount sufficient to pay at maturity the principal of and interest on the Notes.

The Company may, at its option, and at any time, elect to have its obligations discharged with respect to all outstanding Notes. This is referred to as “defeasance.” Such defeasance means that the Company shall be

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deemed to have paid and discharged the entire indebtedness represented by the outstanding Notes and to have satisfied its other obligations with respect to the Notes under the Indenture, except for (i) the rights of the holders of outstanding Notes to receive, solely from the trust fund described below, payments in respect of the principal of (and premium, if any) and interest on such Notes when such payments are due, (ii) the Company’s obligations with respect to the Notes relating to the issuance of temporary Notes, the registration, transfer and exchange of Notes, the replacement of mutilated, destroyed, lost or stolen Notes, the maintenance of an office or agency for payment of the Notes, and the holding of money for security payments in trust and statements as to compliance with the Indenture, (iii) the rights, powers, trusts, duties and immunities of the trustees under the Indenture and (iv) the defeasance provisions of the Indenture. In addition, the Company may, at its option and at any time, elect to be released from its obligations with respect to certain of the covenants under the Indenture (including those described under “— Certain Covenants — Limitation on Liens on Capital Stock of Restricted Subsidiaries”), referred to as “covenant defeasance”, and any omission to comply with such obligations shall not constitute a default or an event of default with respect to the Notes.

In order to exercise either defeasance or covenant defeasance with respect to the Notes, (i) the Company must irrevocably deposit with the trustee, in trust, for the benefit of the holders of the Notes, cash in U.S. dollars, certain U.S. government obligations, or a combination thereof, in such amounts as will be sufficient, in the opinion of a nationally recognized firm of independent public accountants, to pay the principal of and interest on the outstanding Notes on the stated maturity (or Redemption Date, if applicable) of such principal or installment of interest; (ii) in the case of defeasance, the Company shall have delivered to the trustees an opinion of counsel in the United States stating that (x) the Company has received from, or there has been published by, the Internal Revenue Service a ruling or (y) since the date of the offering memorandum for the Initial Notes, there has been a change in the applicable U.S. federal income tax law, in either case to the effect that, and based thereon such opinion of counsel shall confirm that, the holders of the outstanding Notes will not recognize income, gain or loss for U.S. federal income tax purposes as a result of such defeasance and will be subject to U.S. federal income tax on the same amounts, in the same manner and at the same times as would have been the case if such defeasance had not occurred; (iii) in the case of covenant defeasance, the Company shall have delivered to the trustees an opinion of counsel in the United States to the effect that the holders of the outstanding Notes will not recognize income, gain or loss for U.S. federal income tax purposes as a result of such covenant defeasance and will be subject to U.S. federal income tax on the same amounts, in the same manner and at the same times as would have been the case if such covenant defeasance had not occurred; and (iv) the Company must comply with certain other conditions.

Modification

The Indenture provides that the Company and the trustees may enter into supplemental indentures without the consent of the holders of the Notes or the holders of the securities of any other series to: (a) evidence the succession of another person to the Company and the obligations assumed by such successor under the Indenture; (b) add to the Company’s covenants for the benefit of the holders of the securities of any series or to surrender any right or power conferred upon the Company by the Indenture; (c) add events of default for the benefit of the holders of the securities of any series; (d) change or eliminate any provisions of the Indenture, provided that any such change or elimination shall become effective only when there is no security issued under the Indenture then outstanding of any series created prior thereto which is entitled to the benefit of such provision; (e) secure any series of securities; (f) establish the form and terms of any series of securities permitted to be issued under the Indenture; (g) evidence the acceptance of appointment by a successor trustee under the Indenture and provide for or facilitate the administration of one or more trusts under the Indenture by one or more trustees; (h) cure any ambiguity, correct or supplement any inconsistency or make any other modification, provided that such action does not adversely affect the interests of the holders of outstanding securities of any series in any material respect; and (i) supplement any of the provisions of the Indenture to the extent necessary to permit or facilitate the defeasance or discharge of any series of securities, provided such action does not adversely affect the interests of the holders of securities of any series in any material respect.

The Indenture also contains provisions permitting the Company and the trustees, with the consent of the holders of not less than a majority in principal amount of all securities issued under the Indenture then outstanding and affected (treated as one class), to add any provisions to, change in any manner or eliminate any of the provisions of, the Indenture or modify in any manner the rights of the holders of securities under

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the Indenture; provided that the Company and the trustees may not, without the consent of the holder of each outstanding security affected thereby, among other things: (a) change the stated maturity of the principal of or any installment of interest on any security, (b) reduce the principal amount of or the rate of interest on, or premium payable upon the redemption of, any such security, (c) reduce the amount of the principal of an original issue discount security that would be due and payable upon a declaration of acceleration of the maturity thereof, (d) adversely affect any right of repayment at the option of the holder of any security, (e) change the place or currency of payment of principal of, or any premium or interest on, any such security, (f) impair the right to institute suit for the enforcement of any such payment on any security when due, (g) reduce the percentage in principal amount of securities of any series whose consent is necessary to modify or amend the Indenture or to waive compliance with certain provisions of the Indenture or certain defaults and their consequences or (h) modify the foregoing requirements, except to increase any percentage or to provide that certain provisions of the Indenture cannot be modified or waived without the consent of the holder of each outstanding security affected thereby.

Enforceability of Judgments

Since some of the Company’s assets are in Canada, any judgment obtained outside of Canada against the Company, including any judgment with respect to the payment of principal or interest on the Notes may not be collectible outside of Canada.

The Company has been informed by Torys LLP, counsel to the Company, that a court of competent jurisdiction in the Province of Ontario (an “Ontario Court”) would give a judgment based upon a final and conclusive in personam judgment of a court exercising jurisdiction in the Borough of New York, The City of New York, State of New York (a “New York Court”) for a sum certain, obtained against the Company, with respect to a claim arising out of the Indenture or the Notes (a “New York Judgment”), without reconsideration of the merits, provided that (i) an action to enforce the New York Judgment must be commenced in the Ontario Court within any applicable limitation period; (ii) the Ontario Court has discretion to stay or decline to hear an action on the New York Judgment if the New York Judgment is under appeal or there is another subsisting judgment in any jurisdiction relating to the same cause of action; (iii) the Ontario Court will render judgment only in Canadian dollars; (iv) an action in the Ontario Court on the New York Judgment may be affected by bankruptcy, insolvency or other similar laws affecting the enforcement of creditors’ rights generally; and (v) an action in the Ontario Court on the New York Judgment would be subject to the following defenses: (A) the New York Judgment was obtained by fraud or in a manner contrary to the principles of natural justice but the New York Judgment would not be contrary to natural justice by reason only that service of process was effected on the agent for service of process appointed by the Company pursuant to the Indenture; (B) the New York Judgment is for a claim which under the laws of the Province of Ontario and the federal laws of Canada applicable therein would be characterized as based on a foreign revenue, expropriatory, penal or other public law; (C) the New York Judgment is contrary to Ontario public policy, as such term is interpreted under the laws of the Province of Ontario and the federal laws of Canada applicable therein, or to an order made by the Attorney General of Canada under the Foreign Extraterritorial Measures Act (Canada) or by the Competition Tribunal under the Competition Act (Canada) in respect of certain judgments referred to in these statutes; and (D) the New York Judgment has been satisfied or is void under the laws of the State of New York. In the opinion of such counsel, there are currently no reasons under the law of Ontario for avoiding recognition of said judgments of New York Courts under the Indenture or on the Notes based upon public policy. The Company has been advised by such counsel that a monetary judgment of a U.S. court predicated solely upon civil liability provisions of U.S. federal securities laws would likely be enforceable in Canada if the U.S. court in which judgment was obtained had a basis for jurisdiction that was recognized by a Canadian court for such purposes. The Company has also been advised by its counsel, that it is less certain that an original action could be commenced in Canada on the basis of liability predicated solely upon such laws.

Consent to Jurisdiction

The Indenture provides that the Company has irrevocably appointed CT Corporation System, 28 Liberty Street, New York, New York 10005, as its authorized agent for service of process in any legal action or proceeding arising out of or relating to the Indenture and the Notes for actions brought under United States federal or state securities laws or for actions brought by either trustee or for any actions arising out of or

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related to the Indenture or the Notes in any New York Court, and has irrevocably submitted to the jurisdiction of the New York Courts for such purposes.

Governing Law

The Indenture and the Notes are governed by and shall be construed in accordance with the laws of the State of New York.

Trustees, Paying Agent and Securities Registrar

The Bank of New York Mellon of 240 Greenwich Street, Floor 7E, New York, New York, 10286, U.S.A. currently acts as United States trustee, paying agent and securities registrar for the Notes.

BNY Trust Company of Canada of 1 York St., 6th Floor, Toronto, Ontario, Canada, M5J 0B6 currently acts as Canadian trustee for the Notes.

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PRIOR SALES

On March 1, 2021, the Company issued Cdn$850,000,000 aggregate principal amount of 3.95% Senior Notes Due 2031, priced at 100.008% of the aggregate principal amount, resulting in gross proceeds of Cdn$856.8 million (before the underwriting discount).

On March 3, 2021, the Company issued $600,000,000 aggregate principal amount of Initial Notes, priced at 99.865% of the aggregate principal amount, resulting in gross proceeds of $599.19 million (before the underwriting discount).

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CERTAIN ERISA CONSIDERATIONS

General

The U.S. Employee Retirement Income Security Act of 1974, as amended (“ERISA”), imposes certain requirements on employee benefit plans subject to Title I of ERISA and on entities that are deemed to hold the assets of such plans (“ERISA Plans”), and on those persons who are fiduciaries with respect to ERISA Plans. Investments by ERISA Plans are subject to ERISA’s general fiduciary requirements, including, but not limited to, the requirement of investment prudence and diversification and the requirement that an ERISA Plan’s investments be made in accordance with the documents governing the plan.

Section 406 of ERISA and Section 4975 of the U.S. Internal Revenue Code of 1986, as amended (the “Code”), prohibit certain transactions involving the assets of an ERISA Plan (as well as those plans that are not subject to ERISA but which are subject to Section 4975 of the Code, such as individual retirement accounts (together with ERISA Plans, “Plans”)) and certain persons (referred to as “parties in interest” or “disqualified persons”) having certain relationships to such Plans, unless a statutory or administrative exemption is applicable to the transaction. A party in interest or disqualified person who engages in a prohibited transaction may be subject to excise taxes and other penalties and liabilities under ERISA and the Code.

Any Plan fiduciary which proposes to cause a Plan to acquire the Exchange Notes should consult with its counsel regarding the applicability of the fiduciary responsibility and prohibited transaction provisions of ERISA and Section 4975 of the Code to such an investment, and to confirm that such acquisition and holding will not constitute or result in a non-exempt prohibited transaction or any other violation of an applicable requirement of ERISA.

Non-U.S. plans, governmental plans and certain church plans, while not subject to the fiduciary responsibility provisions of ERISA or the prohibited transaction provisions of ERISA and Section 4975 of the Code, may nevertheless be subject to non-U.S., or U.S. federal, state, local or other laws or regulations that are substantially similar to the foregoing provisions of ERISA and the Code (“Similar Law”). Fiduciaries of any such plans should consult with their counsel before acquiring the Exchange Notes to determine the need for, and the availability, if necessary, of any exemptive relief under applicable Similar Law.

Prohibited Transaction Exemptions

The fiduciary of a Plan that proposes to acquire and hold any Exchange Notes should consider, among other things, whether such purchase and holding may involve (i) the direct or indirect extension of credit to a party in interest or a disqualified person, (ii) the sale or exchange of any property between a Plan and a party in interest or a disqualified person, or (iii) the transfer to, or use by or for the benefit of, a party in interest or disqualified person, of any Plan assets. Such parties in interest or disqualified persons could include, without limitation, the Company, the initial purchasers of the Initial Notes, the holders of senior debt securities of the Company, or any of their respective agents or affiliates. Depending on the satisfaction of certain conditions, which may include the identity of the Plan fiduciary making the decision to acquire or hold the Exchange Notes on behalf of a Plan, Section 408(b)(17) of ERISA or Prohibited Transaction Class Exemption (“PTCE”) 84-14 (relating to transactions effected by a “qualified professional asset manager”), PTCE 90-1 (relating to investments by insurance company pooled separate accounts), PTCE 91-38 (relating to investments by bank collective investment funds), PTCE 95-60 (relating to investments by insurance company general accounts) or PTCE 96-23 (relating to transactions directed by an in-house asset manager) (collectively, the “Class Exemptions”) could provide an exemption from the prohibited transaction provisions of ERISA and Section 4975 of the Code. However, there can be no assurance that any of these Class Exemptions or any other exemption will be available with respect to any particular transaction involving the Exchange Notes.

By its acquisition of any Exchange Note, the acquirer thereof will be deemed to have represented and warranted that either:

(i)

no assets of a Plan or non-U.S., governmental or church plan have been used to acquire such Exchange Notes or an interest therein; or

(ii)

the acquisition and holding of such Exchange Notes or an interest therein by such person do not

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constitute a non-exempt prohibited transaction under ERISA or Section 4975 of the Code or violation of Similar Law.

The foregoing discussion is general in nature. Due to the complexity of the applicable rules and penalties under ERISA, the Code and Similar Laws, each Plan fiduciary (and each fiduciary for non-U.S., governmental or church plans subject to Similar Law) should consult with its legal advisor concerning the potential consequences to the applicable Plan or plan under ERISA, Section 4975 of the Code or such Similar Laws of an investment in the Exchange Notes.

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CERTAIN U.S. FEDERAL INCOME TAX CONSIDERATIONS

The exchange of Initial Notes for Exchange Notes will not be treated as a taxable transaction for U.S. Federal income tax purposes because the terms of the Exchange Notes will not be considered to differ materially in kind or in extent from the terms of the Initial Notes. Rather, the Exchange Notes you receive will be treated as a continuation of your investment in the Initial Notes. As a result, you will not recognize gain or loss upon the exchange of your Initial Notes for Exchange Notes. In addition, your basis and holding period in the Exchange Notes will be the same as your basis and holding period in the Initial Notes exchanged therefor.

IF YOU ARE CONSIDERING EXCHANGING YOUR INITIAL NOTES FOR EXCHANGE NOTES, YOU SHOULD CONSULT YOUR OWN TAX ADVISORS CONCERNING THE TAX CONSEQUENCES OF THE EXCHANGE ARISING UNDER STATE, LOCAL OR FOREIGN LAWS.

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PLAN OF DISTRIBUTION

The Company issued the Initial Notes on March 3, 2021, pursuant to a private placement offering underwritten by BofA Securities, Inc., J.P. Morgan Securities LLC and Citigroup Global Markets Inc. If all the conditions of the Exchange Offer are satisfied, the Company will exchange all Initial Notes that are validly tendered and not validly withdrawn for an equal principal amount of Exchange Notes that have been registered under the Securities Act.

Any broker-dealer that resells or transfers Exchange Notes in the United States that were received by it for its own account pursuant to the Exchange Offer in exchange for Initial Notes acquired by such broker-dealer as a result of market-making or other trading activities and any broker or dealer that participates in a distribution of such Exchange Notes may be deemed to be an “underwriter” within the meaning of the Securities Act, and any profit of any such resale or transfer of Exchange Notes and any commissions or concessions received by any such persons may be deemed to be underwriting compensation under the Securities Act. Accordingly, each such broker-dealer must acknowledge that it will deliver, and must deliver, a prospectus meeting the requirements of the Securities Act in connection with any resale or transfer of such Exchange Notes in the United States. The letter of transmittal states that by acknowledging that it will deliver, and by delivering, such a prospectus, a broker-dealer will not be deemed to admit that it is an “underwriter” within the meaning of the Securities Act.

This short form prospectus, as it may be amended or supplemented from time to time, may be used by a broker-dealer in connection with resales or transfers in the United States of Exchange Notes received in exchange for Initial Notes where such Initial Notes were acquired as a result of market-making or other trading activities. The Company has agreed to make this short form prospectus, as amended or supplemented, available to any broker-dealer for use in connection with any such resale or transfer for a period ending on the earlier of (i) 180 days after the date on which the registration statement relating to the Exchange Offer is declared effective by the SEC and (ii) the date on which participating broker-dealers are no longer required to deliver a prospectus in connection with market-making or other trading activities.

The Company will not receive any proceeds from any sale of Exchange Notes by broker-dealers. Exchange Notes received by broker-dealers for their own account pursuant to the Exchange Offer may be sold from time to time in one or more transactions in the over-the-counter market, in negotiated transactions, through the writing of options on the Exchange Notes or a combination of such methods of resale, at market prices prevailing at the time of resale, at prices related to such prevailing market prices or negotiated prices. Any such resale may be made directly to purchasers or to or through brokers or dealers who may receive compensation in the form of commissions or concessions from any such broker-dealer and/or the purchasers of any such Exchange Notes.

For a period of 180 days after the expiration of the Exchange Offer or, if shorter, for a period ending on the date on which a broker-dealer is no longer required to deliver a prospectus in connection with market-making or other trading activities, the Company will promptly send additional copies of this short form prospectus and any amendment or supplement to this short form prospectus to any broker-dealer that requests such documents in the letter of transmittal. The Company has agreed to (i) pay all expenses incident to the Exchange Offer, other than (a) commissions or concessions of any brokers or dealers, (b) in certain circumstances described under “The Exchange Offer — Terms of the Exchange Offer — Fees and Expenses”, transfer taxes and (c) any other taxes you may incur; and (ii) indemnify the holders of the Initial Notes (including any broker-dealer) against certain liabilities, including liabilities under the Securities Act.

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LEGAL MATTERS

Certain legal matters relating to the Exchange Notes offered by this short form prospectus will be passed upon on our behalf by Torys LLP, New York, New York and Toronto, Canada, with respect to U.S. and Canadian law. As at the date hereof, the partners and associates of Torys LLP, as a group, beneficially own, directly or indirectly, less than 1% of the outstanding securities of the Company.

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INDEPENDENT REGISTERED PUBLIC ACCOUNTING FIRM

PricewaterhouseCoopers LLP, the Company’s Independent Registered Public Accounting Firm, has advised that they are independent of the Company within the meaning of the Rules of Professional Conduct of the Chartered Professional Accountants of Ontario, and independent within the Securities Act, and the applicable rules and regulations adopted by the SEC and the Public Company Accounting Oversight Board (United States).

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AGENT FOR SERVICE OF PROCESS

Brandon W. Sweitzer, Lauren C. Templeton and William C. Weldon are directors of Fairfax who reside outside of Canada. Mr. Sweitzer, Ms. Templeton and Mr. Weldon have appointed the following agent for service of process:

Name of Person or Company			Name and Address of Agent
Brandon W. Sweitzer			Fairfax Financial Holdings Limited 95 Wellington Street West, Suite 800 Toronto, Ontario, M5J 2N7
Lauren C. Templeton			Fairfax Financial Holdings Limited 95 Wellington Street West, Suite 800 Toronto, Ontario, M5J 2N7
William C. Weldon			Fairfax Financial Holdings Limited 95 Wellington Street West, Suite 800 Toronto, Ontario, M5J 2N7

Holders are advised that it may not be possible for investors to enforce judgments obtained in Canada against any person or company that is incorporated, continued or otherwise organized under the laws of a foreign jurisdiction or resides outside of Canada, even if the party has appointed an agent for service of process.

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DOCUMENTS FILED AS PART OF THE REGISTRATION STATEMENT

The following documents have been filed with the SEC as part of the registration statement of which this short form prospectus is a part insofar as required by the SEC’s Form F-10:

•

the documents set forth under “Documents Incorporated by Reference” in this short form prospectus;

•

the Registration Rights Agreement;

•

the consent of PricewaterhouseCoopers LLP, the Company’s independent registered public accounting firm;

•

the consent of Torys LLP, the Company’s U.S. and Canadian counsel;

•

the indenture dated as of December 1, 1993;

•

the first supplemental indenture dated as of May 9, 2011;

•

the third supplemental indenture dated as of February 26, 2021;

•

the form of Note;

•

the statement of eligibility of the trustee on Form T-1;

•

the form of letter of transmittal;

•

the form of notice of guaranteed delivery;

•

the form of letter to DTC participants, including brokers, dealers, commercial banks, trust companies and other nominees; and

•

powers of attorney (included on the signature pages of the registration statement).

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CERTIFICATE OF THE COMPANY

Date: September 17, 2021

This short form prospectus, together with the documents incorporated herein by reference, constitutes full, true and plain disclosure of all material facts relating to the securities offered by this short form prospectus as required by the securities legislation of the Province of Ontario.

	(Signed) V. Prem Watsa Chairman and Chief Executive Officer			(Signed) Jennifer Allen Vice President and Chief Financial Officer
	On behalf of the Board of Directors
	(Signed) Anthony F. Griffiths Director			(Signed) R. William McFarland Director

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PART II

INFORMATION NOT REQUIRED TO BE DELIVERED TO
OFFEREES OR PURCHASERS

Indemnification of Officers and Directors

The by-laws of the Company provide that, subject to the relevant provisions of the Canada Business Corporations Act, the Company shall indemnify a director or officer of the Company, a former director or officer of the Company, or another individual who acts or acted at the Company’s request as a director or officer, or an individual acting in a similar capacity, of another entity, against all costs, charges and expenses, including an amount paid to settle an action or satisfy a judgment, reasonably incurred by the individual in respect of any civil, criminal, administrative, investigative or other proceeding in which the individual is involved because of that association with the Company or such other entity if (i) the individual acted honestly and in good faith with a view to the best interests of the Company or, as the case may be, to the best interests of the other entity for which the individual acted as a director or officer or in a similar capacity at the Company’s request; and (ii) in the case of a criminal or administrative action or proceeding that is enforced by a monetary penalty, the individual has reasonable grounds for believing that the individual’s conduct was lawful.

The Company also maintains insurance for the benefit of its directors and officers against liability in their respective capacities as directors and officers. The directors and officers are not required to pay any premium in respect of the insurance. The policy contains standard industry exclusions.

Insofar as indemnification for liabilities arising under the Securities Act of 1933 may be permitted to directors, officers or persons controlling the Registrant pursuant to the foregoing provisions, the Registrant has been informed that in the opinion of the U.S. Securities and Exchange Commission such indemnification is against public policy as expressed in the Securities Act of 1933 and is therefore unenforceable.

EXHIBITS

Exhibit No.
2.1			Registration Rights Agreement dated as of March 3, 2021, among Fairfax Financial Holdings Limited and the initial purchasers named therein (incorporated by reference to Exhibit 99.2 to our Report on Form 6-K, furnished to the SEC on March 3, 2021)
4.1			Annual Information Form of Fairfax Financial Holdings Limited dated March 5, 2021 for the year ended December 31, 2020 (incorporated by reference to Exhibit 99.1 to our Annual Report on Form 40-F filed with the SEC on March 5, 2021 (the “Form 40-F”))
4.2			Annual audited consolidated financial statements of Fairfax Financial Holdings Limited for the years ended December 31, 2020 and 2019 and Management’s Report on Internal Control over Financial Reporting, and the management’s discussion and analysis for the financial year ended December 31, 2020 (incorporated by reference to Exhibits 99.2 and 99.3 to the Form 40-F)
4.3			Notice of annual meeting of shareholders and management information circular dated March 5, 2021 in respect of the annual meeting of shareholders held on April 15, 2021 (incorporated by reference to Exhibit 99.1 to our Report on Form 6-K, furnished to the SEC on March 5, 2021 (first filing))
4.4			Interim unaudited consolidated financial statements of Fairfax Financial Holdings Limited as at June 30, 2021 and December 31, 2020 and for the three and six month periods ended June 30, 2021 and 2020, and management’s discussion and analysis for the period ended June 30, 2021 (incorporated by reference to Exhibit 99.2 to our Report on Form 6-K, furnished to the SEC on July 29, 2021)
5.1			Consent of PricewaterhouseCoopers LLP
5.2			Consent of Torys LLP
6.1			Powers of Attorney (included on the signature pages hereto)

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Exhibit No.
7.1			Indenture dated as of December 1, 1993 (incorporated by reference to Exhibit 7.1 to our Registration Statement on Form F-10 (File No. 333-228518) filed on November 21, 2018 (the “2018 Registration Statement”))
7.2			First supplemental indenture dated as of May 9, 2011 (incorporated by reference to Exhibit 7.2 to the 2018 Registration Statement)
7.3			Third supplemental indenture dated as of February 26, 2021 (incorporated by reference to Exhibit 99.4 to our Report on Form 6-K, furnished to the SEC on March 1, 2021)
7.4			Form of Note
7.5			Statement of Eligibility and Qualification under the Trust Indenture Act of 1939 on Form T-1
99.1			Form of Letter of Transmittal
99.2			Form of Notice of Guaranteed Delivery
99.3			Form of Letter to DTC Participants

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PART III

UNDERTAKING AND CONSENT TO SERVICE OF PROCESS

Item 1. Undertaking.

The Form F-10 Registrant undertakes to make available, in person or by telephone, representatives to respond to inquiries made by the Commission staff, and to furnish promptly, when requested to do so by the Commission staff, information relating to the securities registered pursuant to this Form F-10 or to transactions in said securities.

Item 2. Consent to Service of Process.

Concurrently with the filing of this Registration Statement, the Form F-10 Registrant is filing with the Commission a written irrevocable consent and power of attorney on Form F-X.

Any change to the name or address of the agent for service of the Form F-10 Registrant shall be communicated promptly to the Commission by amendment to the applicable Form F-X referencing the file number of the relevant registration statement.

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SIGNATURES

Pursuant to the requirements of the Securities Act of 1933, as amended, the registrant certifies that it has reasonable grounds to believe that it meets all of the requirements for filing on Form F-10 and has duly caused this Registration Statement to be signed on its behalf by the undersigned thereunto duly authorized, in the city of Toronto, country of Canada, on September 17, 2021.

FAIRFAX FINANCIAL HOLDINGS LIMITED

By:

/s/ Jennifer Allen

Name:

Jennifer Allen

Title:

Vice President and Chief Financial Officer

POWER OF ATTORNEY

KNOW ALL PERSONS BY THESE PRESENTS, that each person whose signature appears below hereby constitutes and appoints Jennifer Allen and Derek Bulas his or her true and lawful attorney-in-fact and agent, with full power of substitution and resubstitution, for him or her and in his or her name, place and stead, in any and all capacities, to sign any and all amendments (including post-effective amendments) to this registration statement and any registration statements filed by the registrant pursuant to Rule 462(b) of the Securities Act of 1933 relating thereto and to file the same, with all exhibits thereto, and other documents in connection therewith, with the United States Securities and Exchange Commission, granting to said attorney-in-fact and agent, with full power to act alone, full power and authority to do and perform each and every act and thing appropriate or necessary to be done in connection therewith, as fully to all intents and purposes as he or she might or could do in person, hereby ratifying and confirming all that said attorney-in-fact and agent, or his substitute, may lawfully do or cause to be done by virtue hereof.

Pursuant to the requirements of the Securities Act of 1933, as amended, this registration statement has been signed below by the following persons in the capacities and on September 17, 2021.

	Signature			Title
	/s/ V. Prem Watsa V. Prem Watsa			Chairman, Chief Executive Officer and Director (principal executive officer)
	/s/ Jennifer Allen Jennifer Allen			Vice President and Chief Financial Officer (principal financial officer and principal accounting officer)
	/s/ Anthony F. Griffiths Anthony F. Griffiths			Director
	/s/ Robert J. Gunn Robert J. Gunn			Director
	/s/ David L. Johnston David L. Johnston			Director
	/s/ Karen L. Jurjevich Karen L. Jurjevich			Director
	/s/ R. William McFarland R. William McFarland			Director
	/s/ Christine N. McLean Christine N. McLean			Director

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	Signature			Title
	/s/ Timothy R. Price Timothy R. Price			Director
	/s/ Brandon W. Sweitzer Brandon W. Sweitzer			Director
	/s/ Lauren C. Templeton Lauren C. Templeton			Director
	/s/ Benjamin P. Watsa Benjamin P. Watsa			Director
	/s/ William C. Weldon William C. Weldon			Director

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AUTHORIZED UNITED STATES REPRESENTATIVE

Pursuant to the requirements of the Securities Act, this Registration Statement on Form F-10 has been signed below by the undersigned, solely in its capacity as the registrant’s duly authorized representative in the United States, on September 17, 2021.

FAIRFAX (US) INC.

By:

/s/ Eric P. Salsberg

Name:

Eric P. Salsberg

Title:

Director and Vice President

Exhibit 5.1

Consent of Independent Registered Public Accounting Firm

We hereby consent to the incorporation by reference in this Registration Statement on Form F-10 of Fairfax Financial Holdings Limited of our report dated March 5, 2021 relating to the consolidated financial statements and effectiveness of internal control over financial reporting which is filed as an exhibit to Fairfax Financial Holdings Limited’s Annual Report on Form 40-F for the year ended December 31, 2020.

/s/ PricewaterhouseCoopers LLP

Chartered Professional Accountants, Licensed Public Accountants
Toronto, Canada
September 17, 2021

[MISSING IMAGE: tm2127687d3-ftr_pricewter4c.jpg]

Exhibit 5.2

				1114 Avenue of the Americas, 23rd Floor New York, New York 10036.7703 USA P. 212.880.6000 \| F. 212.682.0200
				www.torys.com

September 17, 2021

TO: The Board of Directors of Fairfax Financial Holdings Limited

We hereby consent to the use of our name in the Registration Statement on Form F-10 filed by Fairfax Financial Holdings Limited on September 17, 2021, as such may thereafter be amended or supplemented, and in the short form prospectus contained therein, under the caption “Legal Matters”. In giving such consent we do not thereby admit that we are in the category of persons whose consent is required by the United States Securities Act 1933, as amended or the rules and regulations promulgated thereunder.

Sincerely,

/s/ Torys LLP

Exhibit 7.4

DTC Notes: [UNLESS THIS CERTIFICATE IS PRESENTED BY AN AUTHORIZED REPRESENTATIVE OF THE DEPOSITORY TRUST COMPANY, A NEW YORK CORPORATION (“DTC”), TO THE COMPANY OR ITS AGENT FOR REGISTRATION OF TRANSFER, EXCHANGE, OR PAYMENT AND ANY SUCH CERTIFICATE ISSUED IS REGISTERED IN THE NAME OF CEDE & CO. OR IN SUCH OTHER NAME AS IS REQUESTED BY AN AUTHORIZED REPRESENTATIVE OF DTC (AND ANY PAYMENT IS MADE TO CEDE & CO. OR TO SUCH OTHER ENTITY AS IS REQUESTED BY AN AUTHORIZED REPRESENTATIVE OF DTC), ANY TRANSFER, PLEDGE, OR OTHER USE HEREOF FOR VALUE OR OTHERWISE BY OR TO ANY PERSON IS WRONGFUL INASMUCH AS THE REGISTERED OWNER HEREOF, CEDE & CO., HAS AN INTEREST HEREIN.

THIS SECURITY MAY NOT BE TRANSFERRED EXCEPT AS A WHOLE BY DTC TO A NOMINEE OF DTC OR BY A NOMINEE OF DTC TO DTC OR ANOTHER NOMINEE OF DTC OR BY DTC OR ANY SUCH NOMINEE TO A SUCCESSOR DEPOSITARY OR A NOMINEE OF SUCH SUCCESSOR DEPOSITARY, UNLESS AND UNTIL THIS SECURITY IS EXCHANGED IN WHOLE OR IN PART FOR SECURITIES IN DEFINITIVE FORM.]

Rule 144A Notes: [THIS SECURITY HAS NOT BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED (THE “SECURITIES ACT”), OR ANY STATE SECURITIES LAWS, AND, ACCORDINGLY, MAY NOT BE OFFERED OR SOLD WITHIN THE UNITED STATES OR TO, OR FOR THE ACCOUNT OR BENEFIT OF, U.S. PERSONS EXCEPT AS SET FORTH IN THE FOLLOWING SENTENCE. BY ITS ACQUISITION OF THIS SECURITY, THE HOLDER: (1) REPRESENTS THAT (A) IT IS A “QUALIFIED INSTITUTIONAL BUYER” (AS DEFINED IN RULE 144A UNDER THE SECURITIES ACT), OR (B) IT IS NOT A U.S. PERSON AND IS ACQUIRING THIS SECURITY IN AN OFFSHORE TRANSACTION IN COMPLIANCE WITH REGULATION S UNDER THE SECURITIES ACT; (2) AGREES THAT IT WILL NOT, PRIOR TO EXPIRATION OF THE HOLDING PERIOD APPLICABLE TO SALES OF THIS SECURITY UNDER RULE 144 UNDER THE SECURITIES ACT (OR ANY SUCCESSOR PROVISION), RESELL OR OTHERWISE TRANSFER THIS SECURITY EXCEPT (A) TO THE COMPANY OR ANY SUBSIDIARY THEREOF, (B) TO A QUALIFIED INSTITUTIONAL BUYER IN COMPLIANCE WITH RULE 144A UNDER THE SECURITIES ACT, (C) PURSUANT TO THE EXEMPTION FROM REGISTRATION PROVIDED BY RULE 144 UNDER THE SECURITIES ACT (IF AVAILABLE), (D) PURSUANT TO A REGISTRATION STATEMENT WHICH HAS BEEN DECLARED EFFECTIVE UNDER THE SECURITIES ACT (AND WHICH CONTINUES TO BE EFFECTIVE AT THE TIME OF SUCH TRANSFER) OR (E) OUTSIDE THE UNITED STATES IN COMPLIANCE WITH RULE 904 UNDER THE SECURITIES ACT; AND (3) AGREES THAT IT WILL DELIVER TO EACH PERSON TO WHOM THIS SECURITY IS TRANSFERRED A NOTICE SUBSTANTIALLY TO THE EFFECT OF THIS LEGEND. IF THE PROPOSED TRANSFEREE IS A PURCHASER WHO IS NOT A QUALIFIED INSTITUTIONAL BUYER, THE HOLDER MUST, PRIOR TO SUCH TRANSFER, FURNISH TO THE BANK OF NEW YORK MELLON, AS TRUSTEE (OR A SUCCESSOR TRUSTEE, AS APPLICABLE), SUCH CERTIFICATIONS, LEGAL OPINIONS OR OTHER INFORMATION AS THE COMPANY MAY REASONABLY REQUIRE TO CONFIRM THAT SUCH TRANSFER IS BEING MADE PURSUANT TO AN EXEMPTION FROM, OR IN A TRANSACTION NOT SUBJECT TO, THE REGISTRATION REQUIREMENTS OF THE SECURITIES ACT. THIS LEGEND WILL BE REMOVED UPON THE EARLIER OF THE TRANSFER OF THIS SECURITY PURSUANT TO CLAUSE 2(D) ABOVE OR UPON ANY TRANSFER OF THIS SECURITY UNDER RULE 144 UNDER THE SECURITIES ACT (OR ANY SUCCESSOR PROVISION). AS USED IN THIS SECURITY, THE TERMS “OFFSHORE TRANSACTION,” “UNITED STATES” AND “U.S. PERSON” HAVE THE MEANINGS GIVEN TO THEM BY REGULATION S UNDER THE SECURITIES ACT.]

Reg S Notes: [THIS SECURITY HAS NOT BEEN REGISTERED UNDER THE U.S. SECURITIES ACT OF 1933, AS AMENDED (THE “SECURITIES ACT”), OR ANY STATE OR OTHER SECURITIES LAWS. THE HOLDER HEREOF, BY ACQUISITION OF THIS SECURITY,

AGREES THAT, PRIOR TO THE EXPIRATION OF THE 40-DAY DISTRIBUTION COMPLIANCE PERIOD (AS DEFINED IN REGULATION S (“REGULATION S”) UNDER THE SECURITIES ACT), NEITHER THIS SECURITY NOR ANY INTEREST OR PARTICIPATION HEREIN MAY BE OFFERED, RESOLD, PLEDGED OR OTHERWISE TRANSFERRED WITHIN THE UNITED STATES (AS DEFINED IN REGULATION S) OR TO, OR FOR THE ACCOUNT OR BENEFIT OF, A U.S. PERSON (AS DEFINED IN REGULATION S), EXCEPT TO A QUALIFIED INSTITUTIONAL BUYER IN COMPLIANCE WITH RULE 144A UNDER THE SECURITIES ACT IN A TRANSACTION MEETING THE REQUIREMENTS OF THE INDENTURE REFERRED TO HEREIN.

THE FOREGOING LEGEND MAY BE REMOVED FROM THIS NOTE AFTER 40 DAYS BEGINNING ON AND INCLUDING THE LATER OF (A) THE DATE ON WHICH THE NOTES ARE OFFERED TO PERSONS OTHER THAN DISTRIBUTORS (AS DEFINED IN REGULATION S UNDER THE SECURITIES ACT) AND (B) THE ORIGINAL ISSUE DATE OF THE NOTES.

WITH RESPECT TO ANY SECURITY THAT IS SOLD PURSUANT TO THE ORIGINAL DISTRIBUTION IN CANADA, UNLESS PERMITTED UNDER APPLICABLE SECURITIES LEGISLATION, THE HOLDER OF THIS SECURITY MUST NOT TRADE THE SECURITY BEFORE THE DATE THAT IS FOUR MONTHS AND A DAY AFTER THE DATE ON WHICH THIS SECURITY IS ISSUED.]

FAIRFAX FINANCIAL HOLDINGS LIMITED
(Organized under the laws of Canada)

3.375% SENIOR NOTES DUE 2031

US$

No. CUSIP:

ISIN:

Fairfax Financial Holdings Limited, a corporation duly organized and existing under the laws of Canada (herein called the “Corporation”, which term includes any successor Person under the Indenture hereinafter referred to), for value received, hereby promises to pay to , or its registered assigns, the principal sum of (US$ ) (as may be modified by the Schedule of Increases and Decreases of Global Securities attached here) on March 3, 2031 at the office or agency of the Corporation maintained for such purpose in The City of New York, and to pay interest semi-annually in arrears, on March 3 and September 3 in each year (each, an “Interest Payment Date”), commencing , from March 3, 2021 or from the most recent Interest Payment Date to which interest has been paid or duly provided for, at the rate of 3.375% per annum, until the principal hereof is paid or duly provided for. The interest so payable, and punctually paid or duly provided for, on any Interest Payment Date will, as provided in such Indenture, be paid to the Person in whose name this Security (or one or more Predecessor Securities) is registered at the close of business on the Regular Record Date for such interest, which shall be February 17 or August 17 (whether or not a Business Day), as the case may be, next preceding such Interest Payment Date. Any such interest not so punctually paid or duly provided for shall forthwith cease to be payable to the Holder on such Regular Record Date, and such Defaulted Interest may be paid to the Person in whose name this Security (or one or more Predecessor Securities) is registered at the close of business on a Special Record Date for the payment of such Defaulted Interest to be fixed by the Trustees (as defined below), notice whereof shall be given to Holders of Securities of this series not less than 10 days prior to such Special Record Date, all as more fully provided in said Indenture.

Interest on this Security will be computed on the basis of a 360-day year of twelve 30-day months.

Interest on this Security is subject to any Additional Amounts (as defined below) or Additional Interest (as defined below) that may be payable thereon (as described herein).

This Security is one of the duly authorized Securities of the Corporation (herein called the “Securities”), issued and to be issued in one or more series under an indenture dated as of December 1, 1993 (the “Base Indenture”), among the Corporation, The Bank of New York Mellon, a corporation duly organized and existing under the laws of the State of New York, as the successor U.S. trustee (herein called the “U.S. Trustee”,

which term includes any successor U.S. trustee under the Indenture with respect to the Securities in this series), and BNY Trust Company of Canada, a trust company duly incorporated and existing under the laws of Canada, as the successor Canadian trustee (herein called the “Canadian Trustee”, which term includes any successor Canadian trustee under the Indenture with respect to the Securities of this series, and, collectively with the U.S. Trustee, the “Trustees”) as amended by the first supplemental indenture dated as of May 9, 2011 (the “First Supplemental Indenture”) and the third supplemental indenture dated as of February 26, 2021 (together with the Base Indenture and the First Supplemental Indenture, the “Indenture”) to which is hereby made for a statement of the respective rights, limitations of rights, obligations, duties and immunities thereunder of the Corporation, the Trustees and the Holders of the Securities, and of the terms upon which the Securities are, and are to be, authenticated and delivered. This Security is one of the Securities of the series designated as 3.375% Senior Notes due 2031, unlimited in aggregate principal amount. Additional Securities of this series may be issued by the Corporation from time to time.

The Securities of this series will be direct, unsecured obligations of the Corporation and will rank equally and ratably with all of the Corporation’s other unsecured and unsubordinated indebtedness. The Securities of this series will rank among themselves equally and ratably without preference or priority. The Indenture permits the Corporation from time to time, without notice to or the consent of the Holders of any series of the Securities issued under the Indenture, to create and issue further Securities of this series ranking pari passu with such Securities in all respects and having the same terms as such Securities (except for the issue date, issue price and initial Interest Payment Date following the issue date of such further Securities) and so that such further Securities shall be consolidated and form a single series with, and shall have the same terms as to status, redemption or otherwise as, the Securities of this series; provided that such further Securities will not be issued with the same CUSIP and/or ISIN numbers as this Security unless such further Securities are fungible with this Security for U.S. federal income tax purposes. Any such further Securities shall include any Exchange Securities to be issued in connection with an Exchange Offer (each as defined below under “Registration Rights”), provided that such Exchange Securities shall not be “Exempted Securities” within the meaning of the Indenture and shall not bear the Securities Act legends provided for in Section 204 of the Indenture, and the “Registration Rights” section below (including any Additional Interest (as defined in such section)) shall not apply to such Exchange Securities.

The Securities of this series are not redeemable at the option of the Holder prior to maturity and are not subject to the operation of any sinking fund.

Optional Redemption

The Securities of this series are redeemable at any time prior to December 3, 2030 (the “Par Call Date”), at the option of the Corporation, in whole at any time or in part from time to time, on not less than 15 days’ nor more than 60 days’ prior notice to each Holder of such Securities, upon payment of a Redemption Price equal to the greater of (1) 100% of the principal amount of such Securities to be redeemed; or (2) the sum of the present values of the remaining scheduled payments of principal of and interest on such Securities that would be due if such Securities matured on the Par Call Date (not including any portion of such payments of interest accrued as of the Redemption Date) discounted to the Redemption Date on a semi-annual basis (assuming a 360-day year consisting of twelve 30-day months) at the Treasury Rate plus 30 basis points (the “Make Whole Amount”), plus, in each case, accrued and unpaid interest to, but excluding, the Redemption Date. The Corporation will pay any interest due on an Interest Payment Date that occurs on or prior to a Redemption Date to the registered Holders of the Securities of this series as of the close of business on the Regular Record Date immediately preceding that Interest Payment Date. Unless the Corporation defaults in payment of the redemption price, on and after the applicable Redemption Date, interest will cease to accrue on the Securities or portions thereof called for redemption.

The Securities of this series will be redeemable at any time on or after the Par Call Date, at the option of the Corporation, in whole at any time or in part from time to time, on not less than 15 days’ nor more than 60 days’ prior notice to each Holder, upon payment of a Redemption Price equal to par, together with accrued and unpaid interest to, but excluding, the Redemption Date.

For purposes of determining the Make Whole Amount, the following definitions apply:

“Comparable Treasury Issue” means the United States Treasury security or securities selected by the Quotation Agent as having an actual or interpolated maturity comparable to the remaining term of the Securities of this series from the applicable Redemption Date to the Par Call Date (the “Remaining Life”) of such Securities to be redeemed that would be utilized at the time of selection, and in accordance with customary financial practice, in pricing new issues of corporate debt securities of comparable maturity to the Remaining Life of such Securities to be redeemed.

“Comparable Treasury Price” means, with respect to any Redemption Date, (1) the average of five Reference Treasury Dealer Quotations for such Redemption Date, after excluding the highest and lowest of such Reference Treasury Dealer Quotations or (2) if the Quotation Agent obtains fewer than five Reference Treasury Dealer Quotations, the average of any such Reference Treasury Dealer Quotations.

“Quotation Agent” means the Reference Treasury Dealer appointed by the Corporation.

“Redemption Date” means any date fixed for redemption of Securities.

“Reference Treasury Dealer” means (i) BofA Securities, Inc., J.P. Morgan Securities LLC, Citigroup Global Markets Inc. (or their affiliates that are Primary Treasury Dealers) and their successors; provided, however, that if any of the foregoing shall cease to be a primary United States Government securities dealer in the United States of America (a “Primary Treasury Dealer”), the Corporation will substitute therefor another Primary Treasury Dealer, and (ii) any other Primary Treasury Dealer selected by the Corporation.

“Reference Treasury Dealer Quotation” means, with respect to the Reference Treasury Dealer and any Redemption Date, the average, as determined by the Corporation, of the bid and asked prices for the Comparable Treasury Issue (expressed, in each case, as a percentage of its principal amount) quoted in writing to the Quotation Agent by such Reference Treasury Dealer at 5:00 p.m., New York City time, on the third Business Day preceding such Redemption Date.

Payment of Additional Amounts

All payments made by the Corporation under or with respect to the Securities of this series shall be made free and clear of, and without withholding or deduction for or on account of, any present or future tax, duty, levy, impost, assessment or other governmental charge imposed or levied by or on behalf of the Government of Canada or of any province or territory thereof or by any authority or agency therein or thereof having power to tax (hereinafter “Taxes”), unless the Corporation is required to withhold or deduct Taxes by law or by the interpretation or administration thereof. If the Corporation is so required to withhold or deduct any amount for or on account of Taxes from any payment made under or with respect to the Securities of this series, the Corporation will pay as interest such additional amounts (“Additional Amounts”) as may be necessary so that the net amount received by each Holder of such Securities or the beneficial owner thereof (including Additional Amounts) after such withholding or deduction will not be less than the amount such Holder or beneficial owner would have received if such Taxes had not been withheld or deducted; provided that no Additional Amounts shall be payable with respect to: (a) any payment made to a Holder of the Securities of this series or beneficial owner who is liable for such Taxes in respect of such Securities, (i) by reason of such Holder or beneficial owner, or any other Person entitled to payments on the Securities of this series, being a person with which the Corporation does not deal at arm’s length (within the meaning of the Income Tax Act (Canada) (the “Canadian Tax Act”)), (ii) by reason of such Holder or beneficial owner being a “specified shareholder” of the Corporation or not dealing at arm’s length with a “specified shareholder” of the Corporation (as defined in subsection 18(5) of the Canadian Tax Act), (iii) by reason of the existence of any present or former connection between such Holder or beneficial owner (or between a fiduciary, settlor, beneficiary, member or shareholder of, or possessor of power over, such Holder or beneficial owner, if such Holder or beneficial owner is an estate, trust, partnership, limited liability company or corporation) and Canada or any province or territory thereof or therein or agency thereof or therein other than the mere

acquisition, holding, use or ownership or deemed holding, use or ownership, or receiving payments or enforcing any rights in respect of such Securities as a non-resident or deemed non-resident of Canada or any province or territory thereof or therein or agency thereof or therein, or (iv) by reason of such Holder or beneficial owner’s failure to comply with any certification, identification, documentation or other reporting requirements if compliance is required by law, regulation, administrative practice or an applicable treaty as a pre-condition to exemption from, or a reduction in the rate of deduction or withholding of, such Taxes, in each case, to the extent such Holder or beneficial owner is legally entitled to such exemption or reduction; (b) any estate, inheritance, gift, sales, transfer, excise or personal property tax or any similar Taxes; (c) any Securities of this series presented for payment more than 15 days after the date on which such payment or such Securities became due and payable or the date on which payment thereof is duly provided for, whichever is later (except to the extent that the Holder would have been entitled to such Additional Amounts had such Securities been presented on the last day of such 15-day period); (d) any withholding or deduction imposed on a payment to a Holder or beneficial owner pursuant to Sections 1471 to 1474 of the U.S. Internal Revenue Code of 1986, as amended, or any successor version thereof, or as amended or any successor version thereof, any agreements entered into pursuant to current Section 1471(b)(1) of the Code, and any fiscal or regulatory legislation, rules or official guidance, adopted pursuant to any intergovernmental agreement among governmental authorities entered into in connection with the implementation of the foregoing, and including for greater certainty, Part XVIII and Part XIX of the Canadian Tax Act (“FATCA”), or any Taxes or penalties that arise from the Holder or beneficial owner’s failure to properly comply with its obligations with respect to FATCA or the Canada United States Enhanced Tax Information Exchange Agreement Implementation Act (Canada); (e) any Taxes which are payable otherwise than by withholding or deduction from any payment made under or with respect to the Securities of this series; or (f) any combination of the foregoing clauses (a) to (e); nor shall such Additional Amounts be paid with respect to any payment on any Security of this series to a Holder or beneficial owner who is a fiduciary or partnership or, other than the sole beneficial owner of such Security, to the extent that a beneficiary or settlor with respect to such fiduciary, or a member of such partnership or a beneficial owner thereof would not have been entitled to receive a payment of such Additional Amounts had such beneficiary, settlor, member or beneficial owner received directly its beneficial or distributive share of such payment (collectively, “Excluded Taxes”). The Corporation shall also (a) make such withholding or deduction and (b) remit the full amount deducted or withheld to the relevant authority in accordance with applicable law. Upon the written request of the U.S. Trustee or a Holder of Securities of this series, the Corporation shall furnish, as soon as reasonably practicable, to the U.S. Trustee or such Holder of Securities, as applicable, certified copies of tax receipts evidencing such payment by the Corporation. The Corporation shall indemnify and hold harmless each Holder of Securities of this series and any beneficial owner thereof and, upon written request of any such Holder or beneficial owner, reimburse such Holder or beneficial owner for the amount of (i) any such Taxes (other than Excluded Taxes) so levied or imposed and paid by such Holder or beneficial owner as a result of any failure of the Corporation to withhold, deduct or remit to the relevant tax authority, on a timely basis, the full amounts required under applicable law; and (ii) any such Taxes (other than Excluded Taxes) so levied or imposed with respect to any reimbursement under the foregoing clause (i), so that the net amount received by such Holder or beneficial owner after such reimbursement would not be less than the net amount such Holder or beneficial owner would have received if such Taxes (other than Excluded Taxes) on such reimbursement had not been imposed.

Whenever in the Indenture there is mentioned, in any context, the payment of principal (and premium, if any), Redemption Price, interest or any other amount payable under or with respect to the Securities of this series, such mention shall be deemed to include mention of the payment of Additional Amounts to the extent that, in such context, Additional Amounts are, were or would be payable in respect thereof.

Redemption for Tax Reasons

In the event that the Corporation has become or would become obligated to pay, on the next date on which any amount would be payable under or with respect to the Securities of this series, any Additional Amounts as a result of a change in the laws (including any regulations promulgated thereunder) or treaties of Canada (or any political subdivision or taxing authority thereof or therein), or any change in any official position regarding the application or interpretation of such laws, regulations or treaties, which change is announced and becomes effective on or after the date of issuance of the Securities of this series, then the Corporation may at any time at the Corporation’s option redeem the Securities of this series, in whole, but not in part, at a Redemption Price equal to 100% of their principal amount, plus any interest accrued but not paid

to but excluding the Redemption Date and any additional amounts due and payable on the Securities up to but excluding the Redemption Date.

If the Corporation exercises its option to redeem the Securities, the Corporation will deliver to the trustee a certificate signed by an authorized officer stating that the Corporation is entitled to redeem the Securities to the effect that the circumstances described above exist.

Selection and Notice of Redemption

In the event that the Corporation chooses to redeem less than all of the Securities of this series, selection of such Securities for redemption will be made by the U.S. Trustee in compliance with the requirements of the principal national securities exchange, if any, on which such Securities are listed, or, if such Securities are not so listed, on a pro rata basis, by lot or by such other method in accordance with DTC’s procedures.

No Securities of this series of a principal amount of $2,000 or less shall be redeemed in part. Notice of redemption of Securities of this series held in definitive registered form will be mailed by first-class mail at least 15 days but not more than 60 days before the Redemption Date to each Holder of such Securities to be redeemed at its registered address. Notice of redemption of Securities of this series held in the form of global certificates will be given to DTC in accordance with its applicable procedures (or the procedures of any successor depositary) at least 15 days but not more than 60 days before the Redemption Date. If any Security of this series is to be redeemed in part only, the notice of redemption that relates to such Security shall state the portion of the principal amount thereof to be redeemed. A new Security of this series in principal amount equal to the unredeemed portion thereof will be issued in the name of the Holder thereof upon cancellation of the original Security.

Applicability of Article Eight of the Indenture

Article Eight shall apply to the Securities of this series; provided that Section 801 shall be modified as set forth below (changes indicated in bold and underline):

“Section 801. Corporation May Consolidate, etc. Only on Certain Terms.

The Corporation shall not amalgamate or consolidate with or merge into any other corporation or convey, transfer or lease its properties and assets substantially as an entirety to any other Person, unless:

the corporation formed by such amalgamation or consolidation or into which the Corporation is merged or the Person which acquires by conveyance or transfer, or which leases, the properties and assets (if other than the Corporation) of the Corporation substantially as an entirety (A) shall be a corporation, partnership, company or trust organized and validly existing under the laws of Canada or any province thereof or the United States of America, any state thereof or the District of Columbia and (B) shall expressly assume, by an indenture supplemental hereto, executed and delivered to the Trustees, in form satisfactory to the Trustees, the Corporation’s obligation for the due and punctual payment of the principal of (and premium, if any, on) and interest on all the Outstanding Securities, all other amounts payable by the Corporation pursuant to the Indenture and the performance and observance of every covenant of this Indenture on the part of the Corporation to be performed or observed;

immediately after giving effect to such transaction, no Event of Default, and no event which, after notice or lapse of time or both, would become an Event of Default, shall have occurred or be continuing; and

the Corporation has delivered to the Trustees an Officers’ Certificate and an Opinion of Counsel, each stating that such amalgamation, consolidation, merger, conveyance, transfer or lease and such supplemental indenture comply with this Article and that all conditions precedent herein provided for relating to such transaction have been complied with.

This Section shall only apply to a merger or consolidation in which the Corporation is not the surviving corporation and to conveyances, leases and transfer by the Corporation as transferor or lessor.”

Registration Rights

Holders of the Securities of this series shall have the benefits of a registration rights agreement, dated as of the issue date of such Securities, between the Corporation and BofA Securities, Inc., J.P. Morgan Securities LLC and Citigroup Global Markets Inc., as representatives of the initial purchasers (the “Registration Rights Agreement”), pursuant to which the Corporation has agreed to file a registration statement for an exchange offer (an “Exchange Offer”) of the Securities of this series for new Securities (the “Exchange Securities”), identical in all material respects to this Security, except that the Exchange Securities will be registered under the Securities Act, and the transfer restrictions and registration rights relating to this Security will not apply to the Exchange Securities, or in certain circumstances, a shelf registration statement for the resale of the Securities of this series. In the event of a Registration Default (as defined in the Registration Rights Agreement), additional interest (“Additional Interest”) will accrue on this Security at a rate of 0.25% per annum for the first 90-day period of such Registration Default, increasing by an additional 0.25% per annum for each successive 90-day period of such Registration Default, for maximum Additional Interest of 0.50% per annum.

Upon the completion of the Exchange Offer in accordance with the Registration Rights Agreement, the Corporation shall issue and, upon receipt of a written order of the Corporation in accordance with Section 303 of the Indenture, one of the Trustees shall authenticate (i) one or more Exchange Securities in an aggregate principal amount equal to the principal amount of the beneficial interests in the Regulation S Global Security and/or Restricted Global Security representing Securities of this series accepted for exchange by the Corporation, all as set forth in the written instructions of the Corporation. Concurrently with the issuance of such Exchange Securities, the applicable Trustee shall cause the aggregate principal amount of the Regulation S Global Security and/or Restricted Global Security representing Securities of this series accepted for exchange by the Corporation to be reduced in accordance with the beneficial interests tendered in the Exchange Offer in accordance with the procedures of the DTC (or the procedures of any successor depositary). The Exchange Securities shall not be deemed “Exempted Securities” within the meaning of the Indenture and shall not bear the Securities Act legends provided for in Section 204 of the Indenture, and the paragraph above (including any Additional Interest) shall not apply to such Exchange Securities.

In the event the Corporation is required to pay Additional Interest pursuant to any Registration Rights Agreement, the Corporation will provide written notice to the Trustees of the Corporation’s obligation to pay Additional Interest no later than 15 days prior to the next Interest Payment Date, which notice shall set forth the amount of Additional Interest to be paid by the Corporation. Neither of the Trustees shall at any time be under any duty or responsibility to the Corporation, any Holders or any other Person to determine whether such Additional Interest is payable or the amount thereof.

Events of Default

The Event of Default in respect of this series of Securities are as set forth in Section 501 of the Indenture, except that the Event of Default set forth in Section 501(5) shall be modified as set forth below (changes indicated in bold and underline):

“(5) (A) there shall have occurred a default by the Corporation in the payment, at the stated maturity, of any Debt (including a default with respect to Securities of any series other than that series) in an amount in excess of US$10,000,000 outstanding under or evidenced by any single indenture or instrument (including this Indenture), whether such Debt now exists or shall hereafter be created, and such default shall have continued after any applicable grace period and shall not have been cured or waived or (B) Debt of the Corporation in an amount in excess of US$10,000,000 outstanding under or evidenced by any single indenture or instrument (including this Indenture), whether such Debt now exists or shall hereafter be created, shall have been accelerated or otherwise declared due and payable prior to the stated maturity thereof, and such Debt shall not have been discharged, or such acceleration shall not have been rescinded or annulled, within 10 days after notice thereof shall have been given, by registered or certified mail, to the Corporation by the U.S. Trustee, or to the corporation and the Trustees by the Holders of at least 25% in aggregate principal amount of all of the Securities of the series to which this Section 501(5) applies and are at the time Outstanding; or”

Pursuant to the terms of the Third Supplemental Indenture, the Indenture has been amended to replace references to “$10,000,000” in the above paragraph with references to”$100,000,000”, effective on the Amendment Date.

If an Event of Default with respect to the Securities of this series shall occur and be continuing, the principal of the Securities of this series may be declared due and payable in the manner and with the effect provided in the Indenture.

Modifications and Amendments

The Indenture permits, with certain exceptions as therein provided, the Corporation and the Trustees to enter into supplemental indentures to the Indenture for the purpose of adding any provisions to or changing in any manner or eliminating any of the provisions of the Indenture or of modifying in any manner the rights of the Holders of the Securities under the Indenture with the consent of the Holders of not less than a majority in principal amount of all Outstanding Securities to be affected. The Indenture also permits the Holders of not less than a majority in principal amount of all Outstanding Securities affected, on behalf of the Holders of all such Securities, to waive compliance by the Corporation with certain provisions of the Indenture. In addition, the Holders of not less than a majority in principal amount of the Outstanding Securities of any series, on behalf of the Holders of all of the Securities of such series (or, in some cases, the Holders of not less than a majority in principal amount of all Outstanding Securities, on behalf of the Holders of all such Securities) may waive certain past defaults under the Indenture and their consequences. Any such consent or waiver shall be conclusive and binding upon the Holder of this Security and upon all future Holders of this Security and of any Security issued upon the registration of transfer hereof or in exchange hereof or in lieu hereof, whether or not notation of such consent or waiver is made upon this Security or any such other Security.

No reference herein to the Indenture and no provision of this Security or of the Indenture shall alter or impair the obligation of the Corporation, which is absolute and unconditional, to pay the principal of (and premium, if any, on) and interest on this Security as herein provided and at the place, rate and respective times, and in the coin or currency, herein and in the Indenture prescribed.

Registration; Transfer and Exchange

As provided in the Indenture and subject to certain limitations herein and therein set forth, the transfer of this Security is registerable in the Security Register, upon surrender of this Security for registration of transfer at the office or agency of the Corporation in any place where the principal of and interest on this Security are payable, duly endorsed by, or accompanied by a written instrument of transfer in form satisfactory to the Corporation, the Security Registrar and any transfer agent duly executed by, the Holder hereof or his attorney duly authorized in writing with such signature guaranteed by a commercial bank reasonably acceptable to the Security Registrar or by a member of a national securities exchange, and thereupon one or more new Securities of this series for the same aggregate principal amount will be issued to the designated transferee or transferees.

The Securities of this series are issuable only in registered form without coupons in minimum denominations of US$2,000 and integral multiples of $1,000 in excess thereof. As provided in the Indenture and subject to certain limitations herein and therein set forth, Securities of this series are exchangeable for a like aggregate principal amount of Securities of this series of a different authorized denomination, as requested by the Holder surrendering the same.

No service charge shall be made for any such transfer or exchange, but the Corporation may require payment of a sum sufficient to cover any tax or other governmental charge imposed in connection therewith.

Prior to due presentment of this Security for registration of transfer, the Corporation, the Trustees and any agent of the Corporation or the Trustees may treat the Person in whose name this Security is registered as the owner hereof for all purposes, whether or not this Security is overdue, and neither the Corporation, the Trustees nor any such agent shall be affected by notice to the contrary.

If at any time, (i) DTC or any successor depository notifies the Corporation that it is unwilling or unable to continue as depository for the Securities of this series or if at any time DTC or any successor depository shall no longer be registered as a clearing agency, or in good standing, under the Securities Exchange Act of 1934, as amended, or other applicable statute or regulation and a successor depository registered as a clearing agency under the Securities Exchange Act of 1934, as amended, is not appointed by the Corporation within 90 days after the Corporation receives such notice or becomes aware of such condition, as the case may be or

(ii) the Corporation determines that the Securities of this series shall no longer be represented by a global Security or Securities, then in such event, the Corporation will execute and either of the Trustees will authenticate and deliver Securities of this series in definitive registered form without coupons, in authorized denominations, and in an aggregate principal amount equal to the principal amount of this Security in exchange for this Security. Such Securities in definitive registered form shall be registered in such names and issued in such authorized denominations as DTC or any successor depository, pursuant to instructions from its direct or indirect participants or otherwise shall instruct such Trustee. Such Trustee shall deliver such Securities to the Persons in whose names such Securities are so registered.

Defined Terms

Unless otherwise defined herein, all terms used in this Security which are defined in the Indenture shall have the meanings assigned to them in the Indenture. To the extent that any term of this Security conflicts with any term of the Indenture, the term of this Security shall supersede and replace the applicable term of the Indenture with respect to the Securities of this series (but not the Securities of any other series). Each Holder of this Security, by accepting the same, agrees to and shall be bound by the provisions of the Indenture.

Governing Law

This Security shall be governed by and construed in accordance with the laws of the State of New York.

Authentication

Unless the certificate of authentication hereon has been manually executed by or on behalf of either the U.S. Trustee or the Canadian Trustee, this Security shall not be entitled to any benefits under the Indenture or be valid or obligatory for any purpose.

[Signature page follows.]

IN WITNESS WHEREOF, the Corporation has caused this instrument to be duly executed under its corporate seal.

Dated: , 2021

FAIRFAX FINANCIAL HOLDINGS LIMITED

By:

Name: Jennifer Allen

Title: Vice President and Chief Financial Officer

Attest:

Peter ClarkeVice President and Chief Operating Officer

TRUSTEE’S CERTIFICATE OF AUTHENTICATION
(Certificate of Authentication may be
executed by either Trustee)

This is one of the Securities of the series designated herein referred to in the within-mentioned Indenture.

THE BANK OF NEW YORK MELLON,
as U.S. Trustee

By:

Authorized Signature

[Signature Page]

SCHEDULE OF INCREASES AND DECREASES OF GLOBAL SECURITY

Initial Principal Amount of Global Security: US$

Date

Amount of Increase in
Principal Amount of Global
Security

Amount of Decrease in
Principal Amount of Global
Security

Principal Amount of Global
Security After Increase or
Decrease

Notation by
Registrar or
Security
Custodian

Exhibit 7.5

UNITED STATES
SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549

FORM T-1

STATEMENT OF ELIGIBILITY
UNDER THE TRUST INDENTURE ACT OF 1939 OF A
CORPORATION DESIGNATED TO ACT AS TRUSTEE

CHECK IF AN APPLICATION TO DETERMINE
ELIGIBILITY OF A TRUSTEE PURSUANT TO
SECTION 305(b)(2) ☐

THE BANK OF NEW YORK MELLON
(Exact name of trustee as specified in its charter)

	New York (Jurisdiction of incorporation if not a U.S. national bank)			13-5160382 (I.R.S. employer identification no.)
	240 Greenwich Street, New York, N.Y. (Address of principal executive offices)			10286 (Zip code)

FAIRFAX FINANCIAL HOLDINGS LIMITED
(Exact name of obligor as specified in its charter)

	CANADA (State or other jurisdiction of incorporation or organization)			NOT APPLICABLE (I.R.S. employer identification no.)
	Suite 800, 95 Wellington Street West Toronto, Ontario (Address of principal executive offices)			MSJ 2N7 (Zip code)

3.375% SENIOR NOTES DUE 2031

Debt Securities
(Title of the indenture securities)

General information. Furnish the following information as to the Trustee:

Name and address of each examining or supervising authority to which it is subject.


Name			Address
Superintendent of the Department of Financial Services of the State of New York			One State Street, New York, N.Y. 10004-1417, and Albany, N.Y. 12223
Federal Reserve Bank of New York			33 Liberty Street, New York, N.Y. 10045
Federal Deposit Insurance Corporation			550 17th Street, NW Washington, D.C. 20429
The Clearing House Association L.L.C.			100 Broad Street New York, N.Y. 10004

(b)

Whether it is authorized to exercise corporate trust powers.

Yes.

Affiliations with Obligor.

If the obligor is an affiliate of the trustee, describe each such affiliation.

None.

16.

List of Exhibits.

Exhibits identified in parentheses below, on file with the Commission, are incorporated herein by reference as an exhibit hereto, pursuant to Rule 7a-29 under the Trust Indenture Act of 1939 (the “Act”).

A copy of the Organization Certificate of The Bank of New York Mellon (formerly known as The Bank of New York, itself formerly Irving Trust Company) as now in effect, which contains the authority to commence business and a grant of powers to exercise corporate trust powers. (Exhibit 1 to Amendment No. 1 to Form T-1 filed with Registration Statement No. 33-6215, Exhibits 1a and 1b to Form T-1 filed with Registration Statement No. 33-21672, Exhibit 1 to Form T-1 filed with Registration Statement No. 33-29637, Exhibit 1 to Form T-1 filed with Registration Statement No. 333-121195 and Exhibit 1 to Form T-1 filed with Registration Statement No. 333-152735).

A copy of the existing By-laws of the Trustee (Exhibit 4 to Form T-1 filed with Registration Statement No. 333-229494).

The consent of the Trustee required by Section 321(b) of the Act (Exhibit 6 to Form T-1 filed with Registration Statement No. 333-229519).

A copy of the latest report of condition of the Trustee published pursuant to law or to the requirements of its supervising or examining authority.

SIGNATURE

Pursuant to the requirements of the Act, the trustee, The Bank of New York Mellon, a corporation organized and existing under the laws of the State of New York, has duly caused this statement of eligibility to be signed on its behalf by the undersigned, thereunto duly authorized, all in the City of New York, and State of New York, on the 17th day of September, 2021.

THE BANK OF NEW YORK MELLON

By:

/s/ Wanda Camacho

Name:

Wanda Camacho

Title:

Vice President

Exhibit 99.1

LETTER OF TRANSMITTAL

FAIRFAX FINANCIAL HOLDINGS LIMITED

OFFER TO EXCHANGE

US$600,000,000 OF ITS 3.375% SENIOR NOTES DUE 2031

Pursuant to the Prospectus dated September [•], 2021

THE EXCHANGE OFFER WILL EXPIRE AT 5:00 P.M., NEW YORK CITY TIME, ON OCTOBER [•], 2021 UNLESS EXTENDED (THE “EXPIRATION DATE”). TENDERS MAY BE WITHDRAWN PRIOR TO 5:00 P.M., NEW YORK CITY TIME, ON THE EXPIRATION DATE. WHERE THE EXPIRATION DATE HAS BEEN EXTENDED, TENDERS PURSUANT TO THE EXCHANGE OFFER AS OF THE PREVIOUSLY SCHEDULED EXPIRATION DATE MAY NOT BE WITHDRAWN AFTER THE DATE OF THE PREVIOUSLY SCHEDULED EXPIRATION DATE.

DELIVERY TO:

Bank of New York Mellon, Exchange Agent

BY HAND, MAIL OR OVERNIGHT COURIER:
The Bank of New York Mellon
Corporate Trust — Reorganization Department
2001 Bryan Street, 10 Floor
Dallas, TX 75201

For Information Call:
(315) 414-3034

BY FACSIMILE:
(732) 667-9408
(for eligible institutions only)
Attention: Tiffany Castor

Confirm Receipt of Facsimile by
Telephone: (315) 414-3034

Delivery of this Letter of Transmittal to an address other than as set forth above, or transmission of this Letter of Transmittal via facsimile to a number other than as set forth above, will not constitute a valid delivery. Please read the instructions set forth in this Letter of Transmittal carefully before completing any box below.

The undersigned acknowledges that he, she, they or it has received this Letter of Transmittal (the “Letter”) and the Prospectus dated September [•], 2021 of Fairfax Financial Holdings Limited (the “Issuer”), as it may be amended from time to time (the “Prospectus”), relating to its offer to registered holders (“Holders”) of its issued and outstanding 3.375% Senior Notes due 2031 issued on March 3, 2021 (the “Initial Notes”) to exchange up to US$600,000,000 aggregate principal amount of Initial Notes for a like principal amount of its 3.375% Senior Notes due 2031 (the “Exchange Notes”) which have been registered under the United States Securities Act of 1933, as amended (the “Securities Act”). The Prospectus and this Letter together constitute the Issuer’s offer to exchange its Initial Notes for a like principal amount of its Exchange Notes (the “Exchange Offer”).

As described herein, all Initial Notes properly tendered for exchange will either be exchanged for Exchange Notes or will be returned promptly after the termination or withdrawal of the Exchange Offer. For each Initial Note accepted for exchange, the Holder of such Initial Note will receive an Exchange Note having a principal amount equal to that of, and representing the same indebtedness as that represented by, the surrendered Initial Note. The Exchange Notes will accrue interest from the last interest payment date on which interest was paid on the Initial Notes or, if no interest has been paid on the Initial Notes, from the issue date of the Initial Notes. Accordingly, registered Holders of Exchange Notes on the relevant record date for the first interest payment date following the consummation of the Exchange Offer will receive interest accruing from the last interest payment date on which interest was paid or, if no interest has been paid, from the issue date of the Initial Notes. However, if that record date occurs prior to completion of the Exchange Offer, then the interest payable on the first interest payment date following the completion of the Exchange Offer will be paid to the registered

Holders of the Initial Notes on that record date. Initial Notes accepted for exchange will cease to accrue interest from and after the date of consummation of the Exchange Offer. Holders of Initial Notes whose Initial Notes are accepted for exchange will not receive any payment in respect of accrued interest on such Initial Notes otherwise payable on any interest payment date the record date for which occurs on or after consummation of the Exchange Offer.

This Letter is to be completed by a Holder of Initial Notes if certificates are to be forwarded herewith. Holders of Initial Notes that are tendering by book-entry transfer to the account maintained by the Exchange Agent at The Depository Trust Company (“DTC” or the “Book-Entry Transfer Facility”) can execute the tender through DTC’s Automated Tender Offer Program (“ATOP”), for which this transaction will be eligible, pursuant to the procedures set forth in the Prospectus under the heading “The Exchange Offer — Terms of the Exchange Offer — Book-Entry Transfer”. Holders of Initial Notes who wish to tender and whose certificates are not immediately available, or who are unable to deliver their certificates, this Letter or any other documents required by this Letter or confirmation of the book-entry tender of their Initial Notes into the Exchange Agent’s account at the Book-Entry Transfer Facility (a “Book-Entry Confirmation”) to the Exchange Agent on or prior to the Expiration Date, must tender their Initial Notes according to the guaranteed delivery procedures set forth in the Prospectus under the heading “The Exchange Offer — Terms of the Exchange Offer — Guaranteed Delivery Procedures”. See Instruction 1. Delivery of documents to the Book-Entry Transfer Facility does not constitute delivery to the Exchange Agent.

Tenders by book-entry transfer shall be made by delivering an Agent’s Message in lieu of this Letter. The term “Agent’s Message” means a message, transmitted by the Book-Entry Transfer Facility to and received by the Exchange Agent and forming a part of a Book-Entry Confirmation, which states that the Book-Entry Transfer Facility has received an express acknowledgment from the tendering DTC participant stating that such participant has received and agrees to be bound by this Letter and that the Issuer may enforce this Letter against such participant.

List below the Initial Notes to which this Letter relates. If the space provided below is inadequate, the principal amount of Initial Notes should be listed on a separate signed schedule affixed hereto.

DESCRIPTION OF INITIAL NOTES

(1)	(2)	(3)
Name(s) and Address(es) of Registered Holder(s) of Initial Notes, Exactly as the Name of the Participant Appears on the Book-Entry Transfer Facility Security Position Listing (Please fill in, if blank)	Aggregate Principal Amount	Principal Amount of Initial Note(s) Tendered*

	TOTAL

Unless otherwise indicated in this column, a holder will be deemed to have tendered ALL of the Initial Notes represented by the Initial Notes indicated in column 2. Initial Notes tendered hereby must be in denominations of principal amount of US$2,000 and any integral multiple of US$1,000 in excess thereof. See Instruction 1.

☐

CHECK HERE IF TENDERED INITIAL NOTES ARE BEING DELIVERED BY BOOK-ENTRY TRANSFER MADE TO THE ACCOUNT MAINTAINED BY THE EXCHANGE AGENT WITH THE BOOK-ENTRY TRANSFER FACILITY AND COMPLETE THE FOLLOWING:

Name of Tendering Institution:

Account Number:

Transaction Code Number:

BY CREDITING THE INITIAL NOTES TO THE EXCHANGE AGENT’S ACCOUNT WITH THE BOOK-ENTRY TRANSFER FACILITY’S ATOP AND BY COMPLYING WITH THE APPLICABLE ATOP PROCEDURES WITH RESPECT TO THE EXCHANGE OFFER, THE HOLDER OF THE INITIAL NOTES ACKNOWLEDGES AND AGREES TO BE BOUND BY THE TERMS OF THIS LETTER OF TRANSMITTAL AND CONFIRMS ON BEHALF OF ITSELF AND THE BENEFICIAL OWNER OF SUCH INITIAL NOTES ALL PROVISIONS OF THIS LETTER OF TRANSMITTAL APPLICABLE TO IT AND SUCH BENEFICIAL OWNERS AS FULLY AS IF SUCH BENEFICIAL OWNERS HAD COMPLETED THE INFORMATION REQUIRED HEREIN AND EXECUTED AND TRANSMITTED THIS LETTER OF TRANSMITTAL.

☐

CHECK HERE IF TENDERED INITIAL NOTES ARE BEING DELIVERED PURSUANT TO A NOTICE OF GUARANTEED DELIVERY PREVIOUSLY SENT TO THE EXCHANGE AGENT AND COMPLETE THE FOLLOWING:

Name(s) of Registered Holder(s):

Window Ticket Number (if any):

Date of Execution of Notice of Guaranteed Delivery:

Name of Institution That Guaranteed Delivery:

Account Number:

Transaction Code Number:

☐

CHECK HERE IF YOU ARE A BROKER-DEALER ENTITLED, PURSUANT TO THE TERMS OF THE EXCHANGE AND REGISTRATION RIGHTS AGREEMENT REFERRED TO IN THE PROSPECTUS, TO RECEIVE, AND WISH TO RECEIVE, 10 ADDITIONAL COPIES OF THE PROSPECTUS AND 10 COPIES OF ANY AMENDMENTS OR SUPPLEMENTS THERETO WITHIN 180 DAYS AFTER THE EXPIRATION DATE.

Name:

Address:

IF THE UNDERSIGNED IS NOT A BROKER-DEALER, THE UNDERSIGNED REPRESENTS THAT IT IS NOT PARTICIPATING IN, AND DOES NOT INTEND TO PARTICIPATE IN, A DISTRIBUTION OF EXCHANGE NOTES. IF THE UNDERSIGNED IS A BROKER-DEALER THAT WILL RECEIVE EXCHANGE NOTES FOR ITS OWN ACCOUNT IN EXCHANGE FOR INITIAL NOTES THAT WERE ACQUIRED AS A RESULT OF MARKET-MAKING ACTIVITIES OR OTHER TRADING ACTIVITIES, IT ACKNOWLEDGES AND REPRESENTS THAT IT WILL DELIVER A PROSPECTUS MEETING THE REQUIREMENTS OF THE SECURITIES ACT, IN CONNECTION WITH ANY RESALE OF SUCH EXCHANGE NOTES; HOWEVER, BY SO ACKNOWLEDGING AND REPRESENTING AND BY DELIVERING SUCH A PROSPECTUS THE UNDERSIGNED WILL NOT BE DEEMED TO ADMIT THAT IT IS AN “UNDERWRITER” WITHIN THE MEANING OF THE SECURITIES ACT. IF THE UNDERSIGNED IS A BROKER-DEALER THAT WILL RECEIVE EXCHANGE NOTES, IT REPRESENTS THAT THE INITIAL NOTES TO BE EXCHANGED FOR THE EXCHANGE NOTES WERE ACQUIRED AS A RESULT OF MARKET-MAKING ACTIVITIES OR OTHER TRADING ACTIVITIES. IN ADDITION, SUCH BROKER-DEALER REPRESENTS THAT IT IS NOT ACTING ON BEHALF OF ANY PERSON WHO COULD NOT TRUTHFULLY MAKE THE FOREGOING REPRESENTATIONS.

PLEASE READ THE ACCOMPANYING INSTRUCTIONS CAREFULLY

Ladies and Gentlemen:

Upon the terms and subject to the conditions of the Exchange Offer, the undersigned hereby tenders to the Issuer the aggregate principal amount of Initial Notes indicated above. Subject to, and effective upon, the acceptance for exchange of the Initial Notes tendered hereby, the undersigned hereby sells, assigns and transfers to, or upon the order of, the Issuer all right, title and interest in and to such Initial Notes as are being tendered hereby.

The undersigned hereby irrevocably constitutes and appoints the Exchange Agent as the undersigned’s true and lawful agent and attorney-in-fact with respect to such tendered Initial Notes, with full power of substitution (with full knowledge that the Exchange Agent also acts as agent of the Issuer), among other things, to cause the Initial Notes to be assigned, transferred and exchanged.

The undersigned hereby represents and warrants that the undersigned has full power and authority to tender, sell, assign and transfer the Initial Notes, and to acquire Exchange Notes issuable upon the exchange of such tendered Initial Notes, and that, when such Initial Notes are accepted for exchange, the Issuer will acquire good and unencumbered title thereto, free and clear of all liens, restrictions, charges and encumbrances and not subject to any adverse claim when the same are accepted by the Issuer. The undersigned hereby further represents and warrants that any Exchange Notes acquired in exchange for Initial Notes tendered hereby will have been acquired in the ordinary course of business of the person receiving such Exchange Notes, whether or not such person is the undersigned, that neither the Holder of such Initial Notes nor any such other person is participating in, intends to participate in or has an arrangement or understanding with any person to participate in the distribution (within the meaning of the Securities Act) of Initial Notes or Exchange Notes, that neither the Holder of such Initial Notes nor any such other person is an “affiliate,” as defined in Rule 405 under the Securities Act, of the Issuer and that neither the Holder of such Initial Notes nor such other person is acting on behalf of any person who could not truthfully make the foregoing representations and warranties.

The undersigned acknowledges that this Exchange Offer is being made in reliance on interpretations by the staff of the Securities and Exchange Commission (the “SEC”), as set forth in no-action letters issued to third parties, that the Exchange Notes issued pursuant to the Exchange Offer in exchange for the Initial Notes may be offered for resale, resold and otherwise transferred by Holders thereof (other than any such Holder that is a broker-dealer or an “affiliate” of the Issuer within the meaning of Rule 405 under the Securities Act), without compliance with the registration and prospectus delivery provisions of the Securities Act, provided that such Exchange Notes are acquired in the ordinary course of such Holder’s business, at the time of commencement of the Exchange Offer such Holder has no arrangement or understanding with any person to participate in a distribution of such Exchange Notes, and such Holder is not engaged in, and does not intend to engage in, a distribution of such Exchange Notes. However, the SEC has not considered the Exchange Offer in the context of a no-action letter and there can be no assurance that the staff of the SEC would make a similar determination with respect to the Exchange Offer as in other circumstances. If the undersigned is not a broker-dealer, the undersigned represents that it is not engaged in, and does not intend to engage in, a distribution of Exchange Notes and has no arrangement or understanding to participate in a distribution of Exchange Notes. If the undersigned is a broker-dealer that will receive Exchange Notes for its own account in exchange for Initial Notes, it represents that the Initial Notes to be exchanged for the Exchange Notes were acquired by it as a result of market-making activities or other trading activities and acknowledges that it will deliver a prospectus meeting the requirements of the Securities Act in connection with any resale of such Exchange Notes; however, by so acknowledging and by delivering a prospectus meeting the requirements of the Securities Act, the undersigned will not be deemed to admit that it is an “underwriter” within the meaning of the Securities Act.

The SEC has taken the position that such broker-dealers may fulfill their prospectus delivery requirements with respect to the Exchange Notes (other than a resale of Exchange Notes received in exchange for an unsold allotment from the original sale of the Initial Notes) with the Prospectus. The Prospectus, as it may be amended or supplemented from time to time, may be used by certain broker-dealers (as specified in the Registration Rights Agreement referenced in the Prospectus) (“Participating Broker-Dealers”) for a period of time, starting on the Expiration Date and ending on the earlier of the close of business 180 days after the Expiration Date in

connection with the sale or transfer of such Exchange Notes or such time as such Participating Broker-Dealers no longer own any Initial Notes, other than Initial Notes acquired from the Issuer. The Issuer has agreed that, for such period of time, it will make the Prospectus (as it may be amended or supplemented) available to such a broker-dealer which elects to exchange Initial Notes, acquired for its own account as a result of market making or other trading activities, for Exchange Notes pursuant to the Exchange Offer for use in connection with any resale of such Exchange Notes. By accepting the Exchange Offer, each broker-dealer that receives Exchange Notes pursuant to the Exchange Offer acknowledges and agrees to notify the Issuer prior to using the Prospectus in connection with the sale or transfer of Exchange Notes and that, upon receipt of notice from the Issuer of the happening of any event which makes any statement in the Prospectus untrue in any material respect or which requires the making of any changes in the Prospectus in order to make the statements therein (in light of the circumstances under which they were made) not misleading, such broker-dealer will suspend use of the Prospectus until (i) the Issuer has amended or supplemented the Prospectus to correct such misstatement or omission and (ii) the Issuer has furnished copies of the amended or supplemented Prospectus to such broker-dealer or, if the Issuer has not otherwise agreed to furnish such copies and declines to do so after such broker-dealer so requests, such broker-dealer has obtained a copy of such amended or supplemented Prospectus as filed with the SEC. Except as described above, the Prospectus may not be used for or in connection with an offer to resell, a resale or any other retransfer of Exchange Notes. A broker-dealer that acquired Initial Notes in a transaction other than as part of its market-making activities or other trading activities will not be able to participate in the Exchange Offer.

The undersigned will, upon request, execute and deliver any additional documents deemed by the Issuer to be necessary or desirable to complete the sale, assignment and transfer of the Initial Notes tendered hereby. All authority conferred or agreed to be conferred in this Letter and every obligation of the undersigned hereunder shall be binding upon the successors, assigns, heirs, executors, administrators, trustees in bankruptcy and legal representatives of the undersigned and shall not be affected by, and shall survive, the death or incapacity of the undersigned. This tender may be withdrawn only in accordance with the procedures set forth in the Prospectus under the heading “Exchange Offer — Terms of the Exchange Offer — Withdrawal of Tenders”.

Unless otherwise indicated herein in the box entitled “Special Issuance Instructions” below, please credit the account indicated above maintained at the Book-Entry Transfer Facility.

THE UNDERSIGNED, BY COMPLETING THE BOX ENTITLED “DESCRIPTION OF INITIAL NOTES” ABOVE AND SIGNING THIS LETTER, WILL BE DEEMED TO HAVE TENDERED THE INITIAL NOTES AS SET FORTH IN SUCH BOX ABOVE.

PLEASE READ THIS ENTIRE LETTER OF TRANSMITTAL CAREFULLY BEFORE COMPLETING ANY BOX ABOVE.

PLEASE SIGN HERE
(TO BE COMPLETED BY ALL TENDERING HOLDERS)


SIGNATURE(S) OF OWNER			DATE
Area Code and Telephone Number

If a Holder is tendering an Initial Note, this Letter must be signed by the registered Holder(s) as the name(s) appear(s) on the certificate(s) for the Initial Note or by any person(s) authorized to become registered Holder(s) by endorsements and documents transmitted herewith. If signature is by a trustee, executor, administrator, guardian, officer or other person acting in a fiduciary or representative capacity, please set forth the full title. See Instruction 2.

	Name(s):
				(PLEASE TYPE OR PRINT)
	Capacity:
	Address:
	SIGNATURE GUARANTEE (IF REQUIRED BY INSTRUCTION 2) SIGNATURE(S) GUARANTEED BY AN ELIGIBLE INSTITUTION:

				(AUTHORIZED SIGNATURE)

				(TITLE)

				(NAME AND FIRM)
	DATED:

SPECIAL ISSUANCE INSTRUCTIONS
(See Instructions 2 and 3)

To be completed ONLY if Initial Notes delivered by book-entry transfer which are not accepted for exchange are to be returned by credit to an account maintained at the Book-Entry Transfer Facility other than the account indicated above.

	Issue: Exchange Notes and/or Initial Notes to:
				(Please Type or Print)
	Names(s) and Taxpayer Identification or Social Security Number(s):


	(Please Type or Print)
	Address:

	(Zip Code)

☐

Credit unexchanged Initial Notes delivered by book-entry transfer to the Book-Entry Transfer Facility account set forth below:

(Book-Entry Transfer Facility Account Number, if Applicable)

IMPORTANT: UNLESS GUARANTEED DELIVERY PROCEDURES ARE COMPLIED WITH, THIS LETTER OR A FACSIMILE HEREOF (TOGETHER WITH A BOOK-ENTRY CONFIRMATION AND ALL OTHER REQUIRED DOCUMENTS) MUST BE RECEIVED BY THE EXCHANGE AGENT PRIOR TO 5:00 P.M., NEW YORK CITY TIME, ON THE EXPIRATION DATE.

INSTRUCTIONS FORMING PART OF THE TERMS AND CONDITIONS OF THE OFFER TO EXCHANGE ANY AND ALL OUTSTANDING 3.375% SENIOR NOTES DUE 2031, ISSUED ON MARCH 3, 2021, OF FAIRFAX FINANCIAL HOLDINGS LIMITED FOR 3.375% SENIOR NOTES DUE 2031 OF FAIRFAX FINANCIAL HOLDINGS LIMITED THAT HAVE BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED.

Delivery of this Letter and notes; guaranteed delivery procedures. This Letter is to be completed by Holders of Initial Notes if certificates are to be forwarded herewith. If tenders are to be made pursuant to the procedures for delivery by book-entry transfer set forth in the Prospectus under the heading “The Exchange Offer — Terms of the Exchange Offer — Book-Entry Transfer”, Holders of Initial Notes must deliver a Book-Entry Confirmation. Certificates for all physically tendered Initial Notes, as well as a properly completed and duly executed Letter (or manually signed facsimile hereof), with any required signature guarantees, and any other documents required by this Letter, or Book-Entry Confirmation, as the case may be, must be received by the Exchange Agent on or prior to the Expiration Date, or the tendering Holder must comply with the guaranteed delivery procedures set forth below. Initial Notes tendered hereby must be in denominations of principal amount of US$2,000 and any integral multiple of US$1,000 in excess thereof.

Holders whose certificates for Initial Notes are not immediately available or who cannot deliver their certificates and all other required documents to the Exchange Agent on or prior to the Expiration Date, or who cannot complete the procedure for book-entry transfer on a timely basis, may tender their Initial Notes pursuant to the guaranteed delivery procedures set forth in the Prospectus under the heading “The Exchange Offer — Terms of the Exchange Offer — Guaranteed Delivery Procedures”. Pursuant to such

procedures, (i) such tender must be made through an Eligible Institution (as defined herein), (ii) prior to 5:00 p.m., New York City time, on the Expiration Date, the Exchange Agent must receive from such Eligible Institution a properly completed and duly executed Notice of Guaranteed Delivery, substantially in the form provided by the Issuer (by facsimile transmission (if no medallion guarantee is required), mail or hand delivery), setting forth the name and address of the Holder of Initial Notes and the amount of Initial Notes tendered stating that the tender is being made thereby and guaranteeing that within three business days after the Expiration Date, the certificates for all physically tendered Initial Notes, in proper form for transfer, an executed copy of this Letter as the case may be, and any other documents required by this Letter, or a Book-Entry Confirmation, as the case may be, will be deposited by the Eligible Institution with the Exchange Agent, and (iii) the certificates for all physically tendered Initial Notes, in proper form for transfer, and all other documents required by this Letter, or a Book-Entry Confirmation, are received by the Exchange Agent within three business days after the Expiration Date.

The method of delivery of this Letter and all or any other required documents is at the election and risk of the tendering Holders, but the delivery will be deemed made only when actually received or confirmed by the Exchange Agent. If this Letter and all other required documents are sent by mail, it is suggested that the mailing be registered mail, properly insured, with return receipt requested, made sufficiently in advance of the Expiration Date to permit delivery to the Exchange Agent prior to 5:00 p.m., New York City time, on the Expiration Date. See the “Exchange Offer — Terms of the Exchange Offer” section of the Prospectus.

Signatures on this Letter; bond powers; guarantee of signatures. If this Letter is signed by a participant in the Book-Entry Transfer Facility, the signature must correspond exactly with the name as it appears on the security position listing the Holders of the Initial Notes.

If any tendered Initial Notes are owned of record by two or more joint owners, all of such owners must sign this Letter.

If this Letter is signed by registered Holder(s) of the Initial Notes specified herein and tendered thereby, no separate bond powers are required unless the Exchange Notes are to be issued, or untendered Initial Notes are to be reissued, to a person other than the registered Holder. Signatures on such bond power(s) must be guaranteed by an Eligible Institution.

If this Letter or any bond powers are signed by trustees, executors, administrators, guardians, attorneys-in-fact, officers of corporations or others acting in a fiduciary or representative capacity, such persons should so indicate when signing, and, unless waived by the Issuer, proper evidence satisfactory to the Issuer of their authority to so act must be submitted.

SIGNATURES ON BOND POWERS REQUIRED BY THIS INSTRUCTION 2 MUST BE GUARANTEED BY A FIRM WHICH IS A BANK, BROKER, DEALER, CREDIT UNION, SAVINGS ASSOCIATION OR OTHER ENTITY WHICH IS A MEMBER IN GOOD STANDING OF A RECOGNIZED MEDALLION PROGRAM APPROVED BY THE SECURITIES TRANSFER ASSOCIATION INC., INCLUDING THE SECURITIES TRANSFER AGENTS MEDALLION PROGRAM (“STAMP”), THE STOCK EXCHANGE MEDALLION PROGRAM (“SEMP”) AND THE NEW YORK STOCK EXCHANGE MEDALLION SIGNATURE PROGRAM (“MSP”), OR ANY OTHER “ELIGIBLE GUARANTOR INSTITUTION” (AS DEFINED IN RULE 17AD-15 UNDER THE SECURITIES EXCHANGE ACT OF 1934, AS AMENDED) (EACH OF THE FOREGOING, AN “ELIGIBLE INSTITUTION”).

SIGNATURES ON THIS LETTER NEED NOT BE GUARANTEED BY AN ELIGIBLE INSTITUTION, PROVIDED THE INITIAL NOTES ARE TENDERED: (I) BY A REGISTERED HOLDER OF INITIAL NOTES (WHICH TERM, FOR PURPOSES OF THE EXCHANGE OFFER, INCLUDES ANY PARTICIPANT IN THE BOOK-ENTRY TRANSFER FACILITY SYSTEM WHOSE NAME APPEARS ON A SECURITY POSITION LISTING AS THE HOLDER OF SUCH INITIAL NOTES) WHO HAS NOT COMPLETED THE BOX ENTITLED “SPECIAL ISSUANCE INSTRUCTIONS” IN THIS LETTER, OR (II) FOR THE ACCOUNT OF AN ELIGIBLE INSTITUTION.

Special issuance instructions. Holders tendering Initial Notes by book-entry transfer may request that Initial Notes not exchanged be credited to such account maintained at the Book-Entry Transfer Facility as such Holder may designate herein.

Transfer taxes. The Issuer will pay all transfer taxes, if any, applicable to the transfer of Initial Notes to it or its order pursuant to the Exchange Offer. If, however, Exchange Notes and/or substitute Initial Notes not exchanged are to be delivered to, or are to be registered or issued in the name of, any person other than the registered Holder of the Initial Notes tendered hereby, or if tendered Initial Notes are registered in the name of any person other than the person signing this Letter, or if a transfer tax is imposed for any reason other than the transfer of Initial Notes to the Issuer or its order pursuant to the Exchange Offer, the amount of any such transfer taxes (whether imposed on the registered Holder or any other persons) will be payable by the tendering Holder. If satisfactory evidence of payment of such taxes or exemption therefrom is not submitted herewith, the amount of such transfer taxes will be billed directly to such tendering Holder.

Except as provided in this Instruction 4, it will not be necessary for transfer tax stamps to be affixed to the Initial Notes specified in this Letter.

Waiver of conditions. The Issuer reserves the absolute right to waive satisfaction of any or all conditions enumerated in the Prospectus.

No conditional tenders. No alternative, conditional, irregular or contingent tenders will be accepted. All tendering Holders of Initial Notes, by execution of this Letter, shall waive any right to receive notice of the acceptance of their Initial Notes for exchange.

None of the Issuer, the Exchange Agent nor any other person is obligated to give notice of any defect or irregularity with respect to any tender of Initial Notes nor shall any of them incur any liability for failure to give any such notice.

Withdrawal rights. Tenders of Initial Notes may be withdrawn at any time prior to 5:00 p.m., New York City time, on the Expiration Date.

For a withdrawal of a tender of Initial Notes to be effective, a written notice of withdrawal must be received by the Exchange Agent at the address set forth above prior to 5:00 p.m., New York City time, on the Expiration Date. Any such notice of withdrawal must (i) specify the name of the person having tendered the Initial Notes to be withdrawn (the “Depositor”), (ii) identify the Initial Notes to be withdrawn (including the principal amount of such Initial Notes), (iii) specify the number of the account at the Book-Entry Transfer Facility from which the Initial Notes were tendered and specify the name and number of the account at the Book-Entry Transfer Facility to be credited with the withdrawn Initial Notes and otherwise comply with the procedures of such facility, (iv) contain a statement that such Holder is withdrawing its election to have such Initial Notes exchanged, (v) be signed by the Holder in the same manner as the original signature on the Letter by which such Initial Notes were tendered (including any required signature guarantees) or be accompanied by documents of transfer to have the Trustee with respect to the Initial Notes register the transfer of such Initial Notes in the name of the person withdrawing the tender and (vi) specify the name in which such Initial Notes are registered, if different from that of the Depositor. All questions as to the validity, form and eligibility (including time of receipt) of such notices will be determined by the Issuer, whose determination shall be final and binding on all parties. Any Initial Notes so withdrawn will be deemed not to have been validly tendered for exchange for purposes of the Exchange Offer and no Exchange Notes will be issued with respect thereto unless the Initial Notes so withdrawn are validly retendered. Any Initial Notes that have been tendered for exchange but which are not exchanged for any reason (including the termination or withdrawal of the Exchange Offer) will be returned to the tendering Holder thereof without cost to such Holder by being credited to an account maintained with the Book-Entry Transfer Facility for the Initial Notes promptly after withdrawal, rejection of tender or termination of the Exchange Offer. Properly withdrawn Initial Notes may be retendered by following the procedures described above at any time on or prior to 5:00 p.m., New York City time, on the Expiration Date.

Requests for assistance or additional copies. Questions relating to the procedure for tendering, as well as requests for additional copies of the Prospectus and this Letter, and requests for Notices of Guaranteed Delivery and other related documents may be directed to the Exchange Agent, at the address and telephone number indicated above.

IMPORTANT: THIS LETTER OF TRANSMITTAL (OR A FACSIMILE THEREOF, IF APPLICABLE), OR AN AGENT’S MESSAGE TO THE BOOK-ENTRY TRANSFER FACILITY TOGETHER WITH CONFIRMATION OF BOOK-ENTRY AND ALL OTHER REQUIRED DOCUMENTS, MUST BE RECEIVED BY THE EXCHANGE AGENT PRIOR TO 5:00 P.M. NEW YORK CITY TIME, ON THE EXPIRATION DATE.

Exhibit 99.2

NOTICE OF GUARANTEED DELIVERY FOR

FAIRFAX FINANCIAL HOLDINGS LIMITED

OFFER TO EXCHANGE

US$600,000,000 of its 3.375% Senior Notes due 2031

This form or one substantially equivalent hereto must be used to accept the Exchange Offer of Fairfax Financial Holdings Limited (the “Issuer”) made pursuant to the Prospectus, dated September [•], 2021, as it may be amended from time to time (the “Prospectus”), if the certificates for the outstanding 3.375% Senior Notes due 2031 issued on March 3, 2021 (the “Initial Notes”) are not immediately available or if the procedure for book-entry transfer cannot be completed on a timely basis or time will not permit all required documents to reach the Bank of New York Mellon, as exchange agent (the “Exchange Agent”) prior to 5:00 p.m., New York City time, on the Expiration Date of the Exchange Offer.

Such form may be delivered or transmitted by facsimile transmission (if signatures are not required to be medallion guaranteed), mail or hand delivery to the Exchange Agent as set forth below. In addition, in order to utilize the guaranteed delivery procedure to tender the Initial Notes pursuant to the Exchange Offer, a completed, signed and dated Letter of Transmittal (or facsimile thereof) relating to the tender for exchange of Initial Notes (the “Letter of Transmittal”) must also be received by the Exchange Agent within three business days of the Expiration Date. Any Initial Notes tendered pursuant to the Exchange Offer may be withdrawn at any time before the Expiration Date. Where the Expiration Date has been extended, tenders pursuant to the Exchange Offer as of the previously scheduled Expiration Date may not be withdrawn after the date of the previously scheduled Expiration Date. Capitalized terms not defined herein are defined in the Prospectus or the Letter of Transmittal.

BY HAND, MAIL OR OVERNIGHT COURIER:
The Bank of New York Mellon
Corporate Trust — Reorganization Department
2001 Bryan Street, 10 Floor
Dallas, TX 75201

For Information Call:
(315) 414-3034

BY FACSIMILE:
(732) 667-9408
(for eligible institutions only)
Attention: Tiffany Castor

Confirm Receipt of Facsimile by
Telephone: (315) 414-3034

Delivery of this instrument to an address other than as set forth above, or transmission or instructions via facsimile other than as set forth above, will not constitute a valid delivery.

This form is not to be used to guarantee signatures. If a signature on a Letter of Transmittal is required to be guaranteed by an Eligible Institution (as defined in the Letter of Transmittal) under the instructions thereto, such signature guarantee must appear in the applicable space provided in the signature box on the Letter of Transmittal.

PLEASE READ THE ACCOMPANYING INSTRUCTIONS CAREFULLY

Ladies and Gentlemen:

Upon the terms and conditions set forth in the Prospectus and the accompanying Letter of Transmittal, the undersigned hereby tenders to the Issuer the principal amount of Initial Notes set forth below pursuant to the guaranteed delivery procedure described in the “Exchange Offer — Terms of the Exchange Offer — Guaranteed Delivery Procedures” section of the Prospectus.

The undersigned understands that tenders of Initial Notes will be accepted only in principal amount equal to US$2,000 or integral multiples of US$1,000 in excess thereof. Additionally, the undersigned understands that the tenders of Initial Notes pursuant to the Exchange Offer may not be withdrawn after 5:00 p.m., New York City time, on the Expiration Date.

All authority herein conferred or agreed to be conferred by this Notice of Guaranteed Delivery shall survive the death or incapacity of the undersigned and every obligation of the undersigned under this Notice of Guaranteed Delivery shall be binding upon the heirs, personal representatives, executors, administrators, successors, assigns, trustees in bankruptcy and other legal representatives of the undersigned.

PLEASE SIGN AND COMPLETE

	Principal Amount of Initial Notes Tendered (must be in denominations of principal amount of US$2,000 and any integral multiple of US$1,000 in excess thereof):*			Name(s) of Registered Holder(s):
				Address including zip code:
	If Initial Notes will be delivered by book-entry transfer at The Depository Trust Company, insert Account No.:			Telephone Number including Area Code:
				Signature(s) of Registered Owner(s) or Authorized Signatory:


	Date:

This Notice of Guaranteed Delivery must be signed by the Holder(s) of Initial Notes exactly as its (their) name(s) appear on certificates for Initial Notes or a security position listing as the owner of Initial Notes, or by person(s) authorized to become registered Holder(s) by endorsements and documents transmitted with this Notice of Guaranteed Delivery. If signature is by a trustee, executor, administrator, guardian, attorney-in-fact, officer or other person acting in a fiduciary or representative capacity, such person must provide the following information.

Please print name(s) and address(es):

	Name(s):
	Capacity:
	Address(es):

Do not send Initial Notes with this form. Initial Notes should be sent to the Exchange Agent together with a properly completed and duly executed Letter of Transmittal.

GUARANTEE
(Not to be used for signature guarantee)

The undersigned, a member firm of a registered national securities exchange or of the Financial Industry Regulatory Authority, Inc., a commercial bank or trust company having an office or correspondent in the United States or an “Eligible Guarantor Institution” within the meaning of Rule 17Ad-15 under the Securities Exchange Act of 1934, as amended, hereby guarantees that the certificates representing the principal amount of Initial Notes tendered hereby in proper form for transfer, together with a properly completed and duly executed Letter of Transmittal, with any required signature guarantees and any other documents required by the Letter of Transmittal will be received by the Exchange Agent at the address set forth above or timely confirmation of the book-entry transfer of such Initial Notes into the Exchange Agent’s account at The Depository Trust Company pursuant to the procedures set forth in the Prospectus under the heading “The Exchange Offer — Terms of the Exchange Offer — Guaranteed Delivery Procedures” will be received by the Exchange Agent no later than three business days after the Expiration Date.

	Name of Firm:


	Address:


	Zip Code:
	Area Code and Tel. No.:
	Authorized Signature:
	Title:
	Name: (Please Type or Print)
	Dated:

INSTRUCTIONS FOR NOTICE OF GUARANTEED DELIVERY

Delivery of this Notice of Guaranteed Delivery. A properly completed and duly executed copy of this Notice of Guaranteed Delivery and any other documents required by this Notice of Guaranteed Delivery must be received by the Exchange Agent at its address set forth herein prior to 5:00 p.m., New York City time, on the Expiration Date. The method of delivery of this Notice of Guaranteed Delivery and any other required documents to the Exchange Agent is at the election and risk of the Holder and the delivery will be deemed made only when actually received by the Exchange Agent. If delivery is by mail, registered or certified mail properly insured, with return receipt requested, is recommended. In all cases sufficient time should be allowed to assure timely delivery. For a description of the guaranteed delivery procedure, see Instruction 1 of the Letter of Transmittal.

Signatures of this Notice of Guaranteed Delivery. If this Notice of Guaranteed Delivery is signed by a participant of the Book-Entry Transfer Facility whose name appears on a security position listing as the owner of Initial Notes, the signature must correspond with the name shown on the security position listing as the owner of the Initial Notes.

If this Notice of Guaranteed Delivery is signed by a person other than the registered Holder(s) of any Initial Notes listed or a participant of the Book-Entry Transfer Facility, this Notice of Guaranteed Delivery must be accompanied by appropriate bond powers, signed as the name of the participant shown on the Book-Entry Transfer Facility’s security position listing.

If this Notice of Guaranteed Delivery is signed by a trustee, executor, administrator, guardian, attorney-in-fact, officer of a corporation, or other person acting in a fiduciary or representative capacity, such person should so indicate when signing.

Requests for assistance or additional copies. Questions and requests for assistance and requests for additional copies of the Prospectus may be directed to the Exchange Agent at the address specified on the first page hereof. Holders may also contact their broker, dealer, commercial bank, trust company, or other nominee for assistance concerning the Exchange Offer.

Exhibit 99.3

FAIRFAX FINANCIAL HOLDINGS LIMITED

OFFER TO EXCHANGE

US$600,000,000 of its 3.375% Senior Notes due 2031

To DTC Participants, including Brokers, Dealers, Commercial Banks, Trust Companies and other Nominees:

As described in the enclosed Prospectus, dated September [•], 2021 (as it may be amended or supplemented from time to time, the “Prospectus”), and Letter of Transmittal (the “Letter of Transmittal”), Fairfax Financial Holdings Limited, a corporation incorporated and existing under the Canada Business Corporations Act (the “Company”), is offering to exchange (the “Exchange Offer”) up to US$600,000,000 aggregate principal amount of its outstanding 3.375% Senior Notes due 2031 issued on March 3, 2021 (the “Initial Notes”) for a like principal amount of its 3.375% Senior Notes due 2031 (the “Exchange Notes”), that have been registered under the U.S. Securities Act of 1933, as amended (the “Securities Act”), to be issued in minimum denominations of US$2,000 and integral multiples of US$1,000 in excess thereof, upon the terms and subject to the conditions of the enclosed Prospectus and Letter of Transmittal. The terms of the Exchange Notes are identical in all material respects (including, but not limited to, principal amount, interest rate and maturity) to the terms of the Initial Notes for which they may be exchanged pursuant to the Exchange Offer, except that the Exchange Notes (i) will bear a different CUSIP number from the Initial Notes, (ii) will be freely tradable by persons not affiliated with the Company, (iii) will not bear legends restricting their transfer and (iv) will not contain the registration rights and additional interest provisions of the Initial Notes. The Company will accept for exchange all Initial Notes validly tendered and not validly withdrawn according to the terms of the Prospectus and the Letter of Transmittal. Consummation of the Exchange Offer is subject to certain conditions described in the Prospectus.

WE URGE YOU TO PROMPTLY CONTACT YOUR CLIENTS FOR WHOM YOU HOLD INITIAL NOTES REGISTERED IN YOUR NAME OR IN THE NAME OF YOUR NOMINEE. PLEASE BRING THE EXCHANGE OFFER TO THEIR ATTENTION AS PROMPTLY AS POSSIBLE.

Enclosed are copies of the following documents:

1. the Prospectus;

2. the Letter of Transmittal for your use in connection with the tender of Initial Notes and for the information of your clients; and

3. a form of Notice of Guaranteed Delivery.

Your prompt action is requested. Please note that the Exchange Offer will expire at 5:00 p.m., New York City time, on October [•], 2021, or such later date to which the Company may extend the Exchange Offer (the “Expiration Date”).

To participate in the Exchange Offer, certificates for Initial Notes, together with a duly executed and properly completed Letter of Transmittal (or facsimile thereof), together with any required signature guarantees, and any other required documents, or a timely confirmation of a book-entry transfer of such Initial Notes into the account of the Bank of New York Mellon (the “Exchange Agent”), at the book-entry transfer facility, with any required signature guarantees, and any other required documents, must be received by the Exchange Agent prior to 5:00 p.m., New York City time, on the Expiration Date as indicated in the Prospectus and the Letter of Transmittal.

The Company will not pay any fees or commissions to any broker or dealer or to any other persons (other than the Exchange Agent) in connection with the solicitation of tenders of the Initial Notes pursuant to the Exchange Offer. However, the Company will pay or cause to be paid transfer taxes, if any, applicable to the tender of the Initial Notes to it or its order, except as otherwise provided in the Prospectus and Letter of Transmittal.

If holders of the Initial Notes wish to tender, but it is impracticable for them to forward their Initial Notes prior to 5:00 p.m., New York City time, on the Expiration Date or to comply with the book-entry

transfer procedures on a timely basis, a tender may be effected by following the guaranteed delivery procedures described in “The Exchange Offer — Guaranteed Delivery Procedures” section of the Prospectus.

Any inquiries you may have with respect to the Exchange Offer should be addressed to the Exchange Agent at its address and telephone number set forth in the enclosed Prospectus and Letter of Transmittal. Additional copies of the enclosed materials may be obtained from the Exchange Agent.

				Very truly yours,
				Fairfax Financial Holdings Limited

NOTHING CONTAINED HEREIN OR IN THE ENCLOSED DOCUMENTS SHALL CONSTITUTE YOU OR ANY OTHER PERSON AS AN AGENT OF THE COMPANY OR THE EXCHANGE AGENT, OR AUTHORIZE YOU OR ANY OTHER PERSON TO USE ANY DOCUMENT OR MAKE ANY STATEMENTS ON BEHALF OF EITHER OF THEM IN CONNECTION WITH THE EXCHANGE OFFER, OTHER THAN THE DOCUMENTS ENCLOSED HEREWITH AND THE STATEMENTS EXPRESSLY CONTAINED THEREIN.

Enclosures

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Form F-10 FAIRFAX FINANCIAL HOLDIN

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