The 31+ Strangest Deferred Contracts In Sports History

Updated: Feb 26, 2024By Daniel RosenblatCelebrity News

This article originally appeared on Investing.com. It has been republished here with permission.

Bobby Bonilla, Steve Young, and Mario Lemieux @cbssports/twitter.com / stock.adobe/commons.wikimedia.org

Sports contracts are often complex and can be difficult to understand. It can be even more confusing when they involve elements of deferred payments, such as salaries being paid out over multiple years or performance-based bonuses being delayed.

As much as everyone loves a big paycheck, sometimes it pays to wait. From Bobby Bonilla’s now infamous contract with the Mets to the endorsement deals companies like Reebok and McDonald’s have signed with athletes over the years, these are some of the strangest, longest, and most expensive deferred contracts in sports history.

1. Manny Ramirez

Team On The Hook For The Contract: Boston Red Sox
Deferred Money Per Year: $2 million*
Years Of Deferred Contract: 2010-2026

Manny Ramirez’s seven-year $160 million contract with the Boston Red Sox, signed in 2001, included $20 million options for the two years following the conclusion of the initial contract, which would have been for the 2009 and 2010 seasons.

Manny Ramirez ©Billie Weiss/Getty Images

Prior to the deal being fulfilled in its entirety, Ramirez was traded to the Dodgers. However, that didn’t stop him from collecting on the remainder of the deal. Despite not playing in the big leagues since 2011, Manny has received a $2 million paycheck every July 1st from his former team. He will continue earning paychecks from Boston until 2026.

2. Kevin Garnett

Team On The Hook For The Contract: Boston Celtics
Deferred Money Per Year: $5 million*
Years Of Deferred Contract: 2017-2024

One of the most notable deferred contracts in NBA history belongs to Kevin Garnett, who signed a three-year, $51 million extension with the Boston Celtics in 2007. As part of the agreement, Garnett’s contract was structured uniquely, which would see him paid well after retirement.

Kevin Garnett /commons.wikimedia.org

Rather than receiving the total amount upfront, he would receive $35 million of his salary after his playing days were over. This allowed the Celtics to maintain salary cap flexibility during Garnett’s tenure and build a championship-winning team around him.

3. Josh Smith

Team On The Hook For The Contract: Detroit Pistons
Deferred Money Per Year: $5.3 million*
Years Of Deferred Contract: 2016-2020

In 2013, the Detroit Pistons signed Josh Smith to a four-year, $54 million contract. However, after a season and a half with the team, Smith’s performance was less than impressive, and the Pistons released him.

Josh Smith /commons.wikimedia.org

Instead of paying him the rest of Smith’s salary under the terms stipulated in his contract, the team went another route. The Detroit Pistons opted to pay Josh Smith $5.3 million over 5 years to sit at home watching NBA highlights on ESPN instead of letting him play out his contract.

4. Shane Doan

Team On The Hook For The Contract: Phoenix Coyotes
Deferred Money Per Year: $1 million*
Years Of Deferred Contract: 2016-2017

Shane Doan signed a one-year contract extension with the Phoenix Coyotes in 2016 to return as the team’s captain for one more run at the Cup. But the unique part of the deal was the deferred signing bonus of $2.5 million.

Shane Doan ©Christian Petersen/Getty Images

Coming off of a 4-year contract that earned him a little more than $22 million — and now in the twilight of his career —the lifetime Coyote’s latest deal gave him one last hefty paycheck after retirement. As far as the team was concerned, the agreement gave them salary cap flexibility to provide Doan with the best shot possible at hoisting the Cup before hanging up his skates.

5. Alex Rodriguez

Team On The Hook For The Contract: Texas Rangers/New York Yankees
Deferred Money Per Year: $5 million*
Years Of Deferred Contract: 2016-2025

In 2001, Alex Rodriguez signed a historic 10-year contract worth $252 million with the Texas Rangers. But what made the deal unique was the deferred payment structure that pushed some of the salaries to future years, earning him an interest in the process.

Alex Rodriguez /Wikipedia.org

The Deal A-Rod signed with Texas saw $45 million deferred until after the 10-year deal’s completion. However, Rodriguez was traded to the Yankees in 2004, the Rangers were still on the hook for deferred payments of more than $30 million. By 2010, the two parties agreed to pay Alex the rest of the money between 2016 and 2025 at an additional 2% interest.

6. Rick DiPietro

Team On The Hook For The Contract: New York Islanders
Deferred Money Per Year: $1.5 million*
Years Of Deferred Contract: 2013-2029

Rick DiPietro, a former NHL goaltender, signed one of the most infamous deferred contracts in sports history with the New York Islanders. In 2006, the team inked him to a 15-year deal worth $67.5 million, making him the highest-paid goalie.

Rick DiPietro ©Jana Chytilova/Freestyle Photography/Getty Images

However, injuries plagued DiPietro’s career, and he could not live up to expectations. The Islanders bought out his contract in 2013. However, they still have to pay him $1.5 million annually until 2029, despite him not playing for the team. DiPietro’s contract is a cautionary tale of the risks of signing lengthy and expensive deferred contracts.

7. Bruce Sutter

Team On The Hook For The Contract: Atlanta Braves
Deferred Money Per Year: $1.2 million*
Years Of Deferred Contract: 1990-2020

One of the most unusual deferred contracts in sports history belongs to Hall of Fame pitcher Bruce Sutter. Prior to the ’85 season, Sutter signed one of the smartest contracts a professional athlete has signed. The aging legend agreed to a measly $750,000 annual salary for six years. The catch was the contract’s unique clause.

Bruce Sutter ©Scott Cunningham/Getty Images

For the 30 years from 1990-2020, the Atlanta Braves had to pay Bruce $1.2 million annually. That means that if he wanted to, Bruce Sutter could have bought himself a Ferrari a year for 30 years and have enough left over to purchase season tickets to the Braves.

8. Steve Young

Team On The Hook For The Contract: Los Angeles Express
Deferred Money Per Year: $865,000*
Years Of Deferred Contract: 1990-2027

Steve Young, former quarterback of the San Francisco 49ers, had a unique deferred contract during his time with the Los Angeles Express in the USFL. Young’s contract called for a deferred payment of $40 million, to be paid over 43 years.

Steve Young ©/stock.adobe.com

Unfortunately, the USFL folded before Young’s contract was fully realized, and he had to settle for a reduced payment of $4.8 million, losing out on bonuses and incentives that had been worked into the contract. Steve Young ultimately took a loss of approximately $35 million.

9. Bret Saberhagen

Team On The Hook For The Contract: New York Mets
Deferred Money Per Year: $250,000*
Years Of Deferred Contract: 2004-2028

The New York Mets have made some pretty poor decisions over the years regarding deferred contracts. They’ve been paying Bobby Bonilla $1.2 million every July 1st since the start of the millennium, but that’s not where it ends. The Mets signed Bret Saberhagen to a $15.3 million contract in 1992, with some fairly favorable stipulations. Favorable for Bret.

Bret Saberhagen @newsday/Instagram

Aside from the $15+ million he’d received over the duration of the contract, Saberhagen insisted upon a $250,000 annual salary for 25 years beginning in 2004. Unlike most athletes, Bret was looking towards his future after baseball. That adds up to $6.25 million in deferred payments, for those keeping count.

10. Gilbert Arenas

Team On The Hook For The Contract: Orlando Magic
Deferred Money Per Year: $15.5 million*
Years Of Deferred Contract: 2013-2016

Gilbert Arenas, also known as “Agent Zero,” had a unique deferred contract with the Orlando Magic. In 2008, the Washington Wizards signed Arenas to a 6-year $111 million deal. However, during the 2010/11 season, the Wizards shipped him off to Orlando, leaving the Magic on the hook for the grotesque contract.

Less than a season later, after seeing Arenas had lost his mojo, the Magic waived him using the amnesty provision, meaning they were still on the hook for the remaining $62 million of his contract. The payment was deferred to be paid between 2013-2016 and split into four equal payments of $15.5 million.

11. Darryl Strawberry

Team On The Hook For The Contract: New York Mets
Deferred Money Per Year: $54,666*
Years Of Deferred Contract: 2004-2033

In 1990, Darryl Strawberry signed a contract with the Mets that included deferred payments until 2033. The deal was for 40% of Strawberry’s $700,000 salary from 1990 set aside for a retirement annuity with 5.1% interest. Instead of $700,000, Strawberry was set to bring in a little more than $1.6 million, thanks to the deal.

Sadly, Darryl won’t have the opportunity to cash in on the retirement plan he set up. The former Met ran into problems with the tax man. The IRS seized and auctioned off his annuity.

12. Max Scherzer

Team On The Hook For The Contract: Washington Nationals
Deferred Money Per Year: $15 million*
Years Of Deferred Contract: 2022-2028

Max Scherzer signed a 7-year, $210 million contract with the Washington Nationals in 2015, with 3 years of the salary deferred and instead split over 7 years from 2022-2028. This meant that Scherzer would receive $15 million a year for 7 years after the contract expired.

The unique structure of the contract allowed the Nationals to front-load the deal and provide some flexibility for the team’s future. Scherzer lived up to the contract, winning two Cy Young Awards with the Nationals and helping them win their first World Series in 2019.

13. Spencer Haywood

Team On The Hook For The Contract: Denver Rockets
Deferred Money Per Year: $75,000*
Years Of Deferred Contract: 1989-2009

Spencer Haywood was a star for the ABA’s Denver Rockets. As a result, the team wanted to lock him up, and The Rockets signed him to a $1.5 million contract — which was a HUGE deal at the time — but it was severely deferred. So much so that it was to be paid out in $75,000 increments over 20 years starting on his 40th birthday.

Spencer Haywood @sportingnews/twitter.com

Due to uncertainty surrounding the league’s future, Spencer Haywood skipped out on the deal and signed with the NBA’s Supersonics for a 15-year deferred deal worth a total of $1.5 million. The move to the NBA also landed Haywood a $100,000 endorsement deal with Nike.

14. Albert Pujols

Team On The Hook For The Contract: Los Angeles Angles
Deferred Money Per Year: $1 million*
Years Of Deferred Contract: 2023-2033

Albert Pujols signed a massive 10-year, $240 million deal with the Los Angeles Angels in 2011. As part of the contract, Pujols ensured financial stability when his playing days were over. As part of the agreement with the team, Pujols will return to the Angels in a “personal services role” after retiring.

Albert won’t be earning nearly as much annually in his new role, but $1 million per year to provide a new generation of ball players with his accrued knowledge of the game isn’t a bad way to spend the decade after hanging up his cleats.