Largest Guaranteed Money Deals That Became Financial Burdens
The worst sports contracts often involve massive guaranteed sums that quickly turn into salary cap anchors. One of the most infamous is the deal signed by New York Mets third baseman Bobby Bonilla in 1999, which started paying $1.19 million annually in 2011 and continues through 2035, creating a recurring financial burden long after his career ended source. Another example is the massive extension given to quarterback Deshaun Watson by the Cleveland Browns in 2022, which included $230 million guaranteed and quickly became a symbol of risk when legal issues and performance questions emerged source.
In the NBA, the worst sports contracts are often measured by the combination of annual salary and production, such as the deal signed by forward Andre Iguodala to a two-year, $32 million contract with the Golden State Warriors in 2023, which many analysts questioned given his declining role source. Similarly, the New York Islanders' contract with forward John Tavares, signed in 2014 as a seven-year, $77 million offer sheet, remains a cautionary tale of overpaying for a star player who failed to deliver elite production relative to the cap hit source.
Contracts Defined by Dead Money and Cap Hits
Dead money occurs when a team continues to count a portion of a player's salary against its cap after releasing or trading him, and it is a hallmark of the worst sports contracts. The Detroit Lions' decision to release Ndamukong Suh in 2015 after signing him to a six-year, $114 million deal left the team with significant dead cap space, illustrating how a single bad contract can cripple roster flexibility source. In the NHL, the contract of Ilya Kovalchuk, signed with the New Jersey Devils in 2010, was so front-loaded that it was ultimately voided by the NHL, setting a precedent for how extreme structures can backfire source.
The worst sports contracts also include deals where the player's production never justified the cap hit, such as the long-term agreement given to pitcher Zack Greinke by the Arizona Diamondbacks in 2016, which carried a $34.4 million total commitment but was plagued by injuries and inconsistent results source. In the NFL, the Houston Texans' signing of quarterback Deshaun Watson to a fully guaranteed five-year, $230 million deal in 2022 created one of the largest cap liabilities in league history, with the contract widely cited as a cautionary example of prioritizing name value over fit and durability source.