The 10 Worst NFL Contracts of All Time, Ranked

Throughout NFL history, there have been countless contracts that teams have grown to regret over time. Some of those deals have taken time to materialize into disaster, while others have instantly come back to haunt the franchise.

When organizations commit to players and tie up that much money to the future, they have to be sure that the players are franchise-altering while elevating those around them.

What have been the 10 worst NFL contracts of all time? We’ll take an in-depth look at each situation and how it affected the team’s future.

10. Jay Cutler — Chicago Bears, 2014

Seven-year, $126 million contract, including $54 million guaranteed

Prior to the 2014 season — following a disappointing 8-8 2013 campaign, while finishing eighth in the NFC and missing the playoffs — the Bears signed Cutler to a seven-year contract extension that made him the third-highest paid quarterback in the NFL.

In the first year following his deal, the 2006 first-round pick led the league in interceptions, and the Bears never surpassed six wins the following three seasons, leading to his release in 2017.

The overall decision to sign Cutler to an extension of that magnitude was perplexing in itself based on the fact that the former Denver Broncos quarterback was not well-liked and his personality did not represent one of a franchise quarterback. In addition, Cutler only led Chicago to the playoffs once, led in interceptions twice, and simply was not a winning player. He underachieved consistently.

It set back the Bears’ cap space for years and left them in quarterback purgatory, which Chicago may have just gotten out of with Caleb Williams.

9. Matt Flynn – Seattle Seahawks, 2012

Three-year, $19.5 million contract, including $10 million guaranteed

The overall money wasn’t too drastic, but at the same time, the quarterback contract landscape was completely different. In 2012, Peyton Manning carried the highest cap hit among all quarterbacks, with an $18 million cap number, while today, Kyler Murray is the highest cap hit at the position, sitting at $49 million.

Nonetheless, Flynn earned the contract by impressing in an incredibly low sample size (two starts). That investment on a player with that little experience turned out to be the wrong move, as Flynn failed to beat out third-round pick Russell Wilson for the starting job.

Flynn never started for Seattle and was traded the following season to the Raiders for a fifth-round pick. Flynn was beat out by Terrelle Pryor for the starting job, leading to his inevitable release during the season.

8. Carson Wentz — Philadelphia Eagles, 2019

Four-year, $128 million contract, including $107 million guaranteed

Two years after a legitimate MVP season before going down with a torn ACL late in the season, handing the reins to Nick Foles — more on him later.

Wentz followed up his MVP-caliber campaign with an impressive 2018 season, completing 69.6% of his passes (a 9.4% increase from 2017), 3,074 yards, 21 touchdowns and 7 interceptions in 11 games.

Those outputs in consecutive years earned him one of the most lucrative contracts in league history, but the former second-overall pick would never meet those high standards he set for himself in years past.

In that same year, Wentz managed a 9-7 record, earning a playoff berth, but his appearance in the postseason was short lived as he exited the Eagles’ eventual loss to Seattle after nine total snaps due to injury.

The 2020 season was an outright disaster for Wentz and the Eagles and the eventual final nail in the coffin for the once promising quarterback, as he went 3-8-1 as a starter through 12 games while leading the league in interceptions (15).

Just two years after the extension, Philadelphia shipped Wentz to the Indianapolis Colts for a 2021 third-round pick and a 2022 first-round pick. It was a solid package for a player who struggled with injuries and really only had a two-year stretch where he looked remotely close to a franchise quarterback.

Wentz went 9-8 in his lone season with the Colts, but turnovers and a disastrous season finale loss to the lowly Jacksonville Jaguars ended his career as a starting quarterback. He is now the backup quarterback for the Kansas City Chiefs.

7. Nick Foles — Jacksonville Jaguars, 2019

Four-year, $88 million contract, including $50 million guaranteed

Following his playoff run to a Super Bowl victory over the New England Patriots, the Jaguars fell for the trap, signing the former Eagles’ quarterback to an expensive deal that came nowhere close to being worthwhile.

Foles suffered a broken collarbone in the season opener, opening the door for rookie quarterback Gardner Minshew. Foles would return to the lineup later in the season, but he was quickly benched after three underwhelming starts. Minshew earned the starting job and never allowed Foles to see the field again as a member of the Jaguars.

In March 2020, Jacksonville traded Foles to Chicago, with whom he signed a cheaper contract. Investing in Foles turned into 736 passing yards, 3 touchdowns, 2 interceptions and an 0-4 record in his starts.

6. Kenny Golladay – New York Giants, 2021

Four-year, $72 million contract, including $40 million guaranteed

Golladay proved to be one of the most consistent receivers during his tenure with the Detroit Lions, making him one of the most sought-after free agents in 2021.

Basically, if you were one of the teams who missed out on Golladay’s services, consider yourself lucky. The New York Giants were not so lucky, making Golladay one of the highest-paid players at the wide receiver position.

In his first season in New York, the former third-round pick caught only 37 of his 76 targets for 521 yards in 14 games. He followed that up in 2022 with 6 catches for 81 yards. That offseason, the Giants took the bullet and cut ties with the once highly productive wideout, who established himself as a star with Matthew Stafford in Detroit prior to signing with New York.

5. Le’Veon Bell — New York Jets, 2019

Four-year, $52 million contract, including $27 million guaranteed

Bell was arguably the best running back in the league during his time with the Pittsburgh Steelers, which made him feel like he deserved to be the highest-paid player at the position.

That led to Bell holding out the entire 2018 season, as the Steelers did not budge on their stance of not paying the superstar running back before the conclusion of his contract at the time.

Once Bell was allowed to hit free agency, he quickly signed the Jets, who seemingly offered him the most money and security by including $35 million guaranteed. The deal would make Bell the second-highest paid player at the position.

His first season’s production with the Jets was more than feasible, totaling 1,250 yards from scrimmage, but his 4 yards per touch and his 3.2 yards per carry were the lowest marks of his career.

The proceeding season was an absolute dumpster fire, as Bell suffered a hamstring in early October 2020, causing him to serve a stint on the injured reserve. After returning from injury, Bell’s relationship with the organization was already tarnished, as Adam Gase’s pedestrian offensive scheme frustrated many players, including Bell, who voiced his distaste on social media.

New York released Bell after failing to find a trade partner, ending his more-than-disappointing tenure with the Jets. He only played 17 games in New York.

4. Daunte Culpepper — Minnesota Vikings, 2003

10-year, $70 million contract, including $10 million signing bonus

The 2004 season was a historic one for Culpepper, as he threw for 4,717 and 39 touchdowns, earning himself a decade-long contract worth $70 million.

That was about the extent of the deal, as Culpepper struggled mightily the following season, constantly dealing with injuries and was a shell of his former self. It was so bad that the Vikings released the escape hatch, trading the veteran quarterback to the Miami Dolphins one year into the contract.

3. Albert Haynesworth — Washington, 2009

Seven-year, $100 million contract, including $41 million guaranteed

This goes down as one of the biggest blunders because of the red flags and well-known concerns surrounding Haynesworth — allegations of bad work ethic, lack of discipline and poor attention to detail.

Despite that, Washington made him an expensive asset that produced lackluster numbers, surviving only two seasons on the deal — especially during the second season, in which Haynesworth recorded 2.5 sacks and 12 tackles in eight games under a new defensive scheme that altered his playing style.

The relationship between Haynesworth and the organization led to a suspension and being traded to the Patriots the following offseason.

Even New England gave up on Haynesworth halfway through the 2011 season. Tampa Bay signed the disgruntled player for the remainder of the season, but that was the final season Haynesworth played in the NFL.

2. Russell Wilson — Denver Broncos, 2022

Five-year, $242 million contract, including $161 million guaranteed

This is a double whammy, as the Denver Broncos not only signed Wilson to this contract with two years remaining on his current deal, they also shipped two first-round picks and multiple players to the Seattle Seahawks who have proven to be solid contributors in Seattle.

This is another example of a deal that never showed any sign of life, as the Broncos went 4-11 in Wilson’s 15 starts during his first season in Denver. It resulted in Nathaniel Hackett being relieved of his head coaching duties the same year he was hired.

Denver hired Sean Payton that offseason, but it didn’t improve the performance enough, and the Broncos decided it was more worthwhile to take on an $85 million dead cap hit than to have Wilson as their quarterback this season.

Wilson signed a one-year, $1 million deal in the 2024 offseason with the Pittsburgh Steelers and is still being paid $39 million by Denver.

It goes down as one of the worst transactions of all time — but the next one is even worse and will most likely go down as the worst of all time.

1. Deshaun Watson — Cleveland Browns, 2022

Five-year, $230 million contract, fully guaranteed

Similar to the Broncos, the Browns decided to trade for and sign their newly acquired quarterback to a historically awful contract. Except this deal is much worse.

Cleveland traded first-round picks in 2022, 2023 and 2024 to the Houston Texans in exchange for Watson, a third-round pick in 2023 and fourth-round picks in 2022 and 2024.

Long story short: the returns on the investment have been non-existent, with no end in sight.

Acquiring a player who was facing more than 20 sexual harassment accusations is unforgiveable, and because of that, there is no sympathy for the Browns ownership who decided to give the highest fully guaranteed contract in league history to a questionable character.

Watson was suspended 11 games after the transaction, and despite going 5-1 in the final six games, the former Texans quarterback posted a 79.1 passer rating and a 58.2 completion percentage in those starts.

In 2023, Watson suffered a shoulder injury in week 11 that ended his season. The team would turn to Joe Flacco, who looked exponentially better than the 29-year-old quarterback at any point during last season.

This season has been even more troubling, as the Browns are 1-5 through six weeks, have yet to score 20 points in a game, have traded Amari Cooper to the Buffalo Bills, and are virtually done. Watson has averaged 170 passing yards per game while throwing only 5 touchdowns so far this season.

To make matters worse, Cleveland restructured Watson’s contract, creating even less cap flexibility in the future, as Watson will be a $73 million cap hit each of the next two seasons following 2024. There is no way out of this contract, whatsoever.

Any other player would be benched by now, but there is too much money tied to this player with no avenues of escape. It feels like a forced decision to keep Watson in the starting lineup at this point.

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