The 10 Worst NFL Contracts of All Time

The 10 Worst NFL Contracts of All Time

The NFL has signed some insane contracts over the years. Some of them were good while others were bad. Ryan Kirksey breaks down the 10 worst NFL contracts of all time.

10. Jon Gruden, HC, 10 Years, $100 million

What can't a head coach be one of the ten worst contracts of all time, especially when the Oakland Raiders (at the time) committed themselves to 10 years and $100 million of Chucky, in hopes that he would bring the silver and black back to former glory? Gruden won a Super Bowl with Tampa Bay for the 2002 season, but he would never sniff anything close to the playoffs or the 10 years after a scandal emerged. After several disgusting emails emerged that came from Gruden in years past, he resigned in 2021 and reached a settlement with the team for some undisclosed amount to get out of the contract.

9. Nnamdi Asomugha, CB, 5 years, $60 million

Speaking of the Raiders, here is one time when they were smart to not overpay for someone who would soon be past their prime. After three straight Pro-Bowl seasons, Asomugha was a hot commodity heading into the 2011 season. The Philadephia Eagles signed him to a long-term deal despite already having an elite secondary. Asomugha would intercept three passes in 2011, but would only play 17 more games after that season before being out of football forever. The lesson here was not to pay for past years' success. Once Asomugha reached 31 years old, the younger wide receivers were burning him with ease.

8. Nick Foles, QB, 4 Years, $88 million

After starting QB Carson Wentz went down with an injury, Nick Foles led to the Philadephia Eagles to an improbably Super Bowl victory over the New England Patriots in early 2019. He then parlayed that success into a four-year deal with the Jacksonville Jaguars. But Foles would get hurt in the season opener and started just four games that year while the world became enamored with Gardner Minshew mania. Foles would be traded the next offseason and has not been a starting quarterback ever since.

7. Jay Cutler, QB, 7 Years, $126.7 million

In hindsight, giving a $126 million contract to Jay Cutler looks about the worst decision in the history of sports. Perhaps the Bears were blinded by the fact that they got to a Super Bowl with Rex Grossman, but this never worked out for Chicago. The team never made the playoffs in the three years Cutler actually played under this contract and Chicago was happy to cut ties after the guaranteed portion of the deal was complete. Cutler would play 14 more games for the Dolphins before hanging it up for good to go become a reality TV star.

6. Percy Harvin, WR, 6 Years, $67 million

There was always something wrong with Harvin when he actually was out on the field playing. The versatile swiss army knife either was battling migraines, soft tissue injuries or his other teammates no matter where he went. But still, the promise of the 2009 offensive rookie of the year was too much for Seattle to pass up. Harvin would play one and a half seasons for Seattle before being sent to the Jets midway through 2014. He would play seven more games with Buffalo before retiring at the end of 2016.

5. Matt Flynn, QB, 3 Years, $26 million

A three-year contract for just $26 million seems like the change you find in the couch compared to some of these other deals. But Seattle (here they are again on this list) took two starts from Matt Flynn and convinced themselves he was their savior at quarterback. It turns out they could have saved every penny of that contract because they drafted Russell Wilson in the third round that year, which relegated Flynn to the bench until he was traded to Oakland. Flynn attempted nine passes for Seattle, so made more than $1 million per throw based on the guaranteed $10 million part of the deal.

4. Daunte Culpepper, QB, 10 Years, $102 million

After two straight Pro Bowl seasons, including a 2004 year that saw him throw for 39 touchdowns and more than 4,700 yards, the Vikings were ready to lock in their quarterback long-term. Unfortunately, Culpepper would only play one more injury-plagued year in Minnesota before he and his bloated contract would be traded to the Miami Dolphins. Culpepper would only play 31 games over the next five years after signing the deal due to a combination of injuries and poor play.

3. JaMarcus Russell, QB, 6 years, $68 million

Perhaps we shouldn't be too hard on the Raiders in this spot because they were just paying market value for a quarterback they drafted first overall out of LSU in 2007. But for their six-year investment, the Raiders only got parts of three seasons, 25 total games. a career 52% completion percentage, and 18 touchdowns to 23 interceptions. Russell's weight and work ethic would come into question almost immediately and he was out of football in less than three years. This six-year commitment helped lead to a reduced number of years in rookie deals for years to come.

2. Albert Haynesworth, DT, 7 Years, $100 million

Perhaps the biggest defensive albatross contract in history was awarded to Haynesworth by the Washington franchise, who - shall we say - have a checkered past with these types of things. Haynesworth was an elite defensive presence in Tennessee before signing the free agent deal with Washington. He started out well enough in 2009, but then showed up in 2010 out of shape, he couldn't find his way in a new 4-3 defensive scheme and was suspended to end the 2010 season. He would then be traded to New England in 2011 but was sent packing before that season was even over. Haynesworth made his money, but he was nowhere near the defensive monster many thought he could be.

1. Michael Vick, QB, 10 Years, $130 million

The talent was unquestionable. The length of time considering Vick's age was defensible. But of course, the Atlanta Falcons could never know that their prized quarterback, who received the largest deal in NFL history, would be out of the NFL for two years serving time in prison for a dogfighting ring. After he would be released the Falcons let him out of his contract. In the end, Atlanta got two years of underwhelming performances from Vick before his jail time. He would reemerge with some excellent years in Philadelphia later in his career, but Vick would come nowhere near to paying off $130 million in the next 10 years after signing that deal. Vick will remain perhaps the NFL's biggest "What if" question for years to come.

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