The NFL’s free-agent market has often been a fertile ground for teams looking to bolster their rosters with top-tier talent. However, not all signings yield the anticipated results. Over the years, several high-profile contracts have turned into financial nightmares for the teams that inked them, failing to meet expectations due to a combination of underperformance, injuries, or off-field issues.
These are some of the most regrettable NFL contracts in recent memory and explore the costly impact they had on their respective franchises.
14. David Boston – San Diego Chargers
In 2003, the Chargers signed wide receiver David Boston to a seven-year, $47 million contract. Despite his previous success, Boston played only one disappointing season for San Diego, catching just 70 passes for 880 yards. Off-field issues and injuries led to his release after just one year, making this contract a costly mistake for the Chargers.
13. Nate Solder – New York Giants
In 2018, the Giants signed Nate Solder to a four-year, $62 million contract with $34.8 million guaranteed, making him the highest-paid offensive lineman at the time. Solder’s performance didn’t match his hefty price tag, and he opted out of the 2020 season due to COVID-19 concerns. The Giants restructured his contract in 2021, significantly reducing his salary.
12. Javon Walker – Oakland Raiders
In 2008, the Raiders signed Walker to a six-year, $55 million contract with $16 million guaranteed. Walker played just 11 games over two seasons, catching 15 passes for 196 yards and one touchdown. The Raiders paid him $21 million before releasing him in 2010, making it one of the most disastrous free-agent signings ever.
11. Matt Flynn – Seattle Seahawks
In 2012, the Seahawks signed Matt Flynn to a three-year, $20.5 million contract with $9 million guaranteed. Flynn, a backup in Green Bay, had impressed in limited playing time. However, he lost the starting job to rookie Russell Wilson and never started a game for Seattle, making this deal a costly misstep
10. Jay Cutler – Chicago Bears
In 2014, the Bears signed Cutler to a 7-year, $126.7 million contract with $54 million guaranteed. Despite the hefty price tag, Cutler’s performance declined, and he was released just three years into the deal. The Bears were left with significant dead money, making it one of the most regrettable contracts in NFL history.
9. Ndamukong Suh – Miami Dolphins
In 2015, Suh signed a 6-year, $114 million contract with the Dolphins, making him the highest-paid defensive player in NFL history at the time. Despite his talent, Suh’s massive cap hits severely limited Miami’s roster flexibility. The Dolphins released him after just three seasons, eating $22.2 million in dead cap space.
8. Jimmy Graham – Chicago Bears
The Bears signed Graham to a two-year, $16 million deal in 2020, despite his declining production. With only 50 receptions for 456 yards in his first season, Graham’s contract was widely criticized as an overpay for an aging tight end past his prime. The Bears ultimately released him after just one season.
7. Kirk Cousins – Minnesota Vikings
Kirk Cousins’ fully guaranteed $84 million contract with the Vikings in 2018 set a new precedent for NFL deals. While Cousins performed well statistically, the team’s lack of playoff success during his tenure raised questions about the contract’s value. His recent $180 million deal with Atlanta further cements his status as a highly paid, yet divisive quarterback.
6. Carson Wentz – Philadelphia Eagles
In 2019, the Eagles signed Wentz to a four-year, $128 million extension with $107.9 million guaranteed. Despite showing promise, injuries and inconsistent play led to his trade in 2021, leaving Philadelphia with $33.8 million in dead cap. This contract serves as a cautionary tale for premature quarterback extensions.
5. Michael Vick – Atlanta Falcons
In 2004, Vick signed a 10-year, $130 million contract with the Falcons, making him the highest-paid player in NFL history at the time. However, his involvement in a dogfighting scandal led to his imprisonment and contract termination, leaving the Falcons with significant financial losses and dead cap space.
4. Russell Wilson – Denver Broncos
The Broncos’ five-year, $242.5 million contract with Russell Wilson in 2022 quickly became a disaster. After just two underwhelming seasons, Denver released Wilson, taking on a staggering $85 million dead money hit over two years. They’re now paying him $37.8 million in 2024 to play for the Steelers.
3. Brock Osweiler – Houston Texans
In 2016, the Texans signed Osweiler to a four-year, $72 million contract with $37 million guaranteed. After just one disastrous season, Houston traded Osweiler and a second-round pick to Cleveland to offload his contract. The Texans essentially paid $16 million for 15 touchdowns and 16 interceptions.
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2. Albert Haynesworth – Washington Redskins
In 2009, the Redskins signed Haynesworth to a seven-year, $100 million deal with $41 million guaranteed. This massive contract quickly became a disaster, as Haynesworth’s performance declined dramatically. He played only 20 games over two seasons before being traded, making it one of the most infamous free-agent busts in NFL history.
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1. Deshaun Watson – Cleveland Browns
The Browns signed Watson to a fully guaranteed 5-year, $230 million contract in 2022, despite pending sexual misconduct allegations. Watson has played only 12 games in two seasons due to suspension and injuries, with mediocre performance. His massive cap hits severely limit Cleveland’s roster flexibility through 2026.