Free agency is a critical component of NFL team-building, but not all signings yield the expected returns on investment.
Some high-profile acquisitions have turned into costly missteps that got players paid big checks for low-end performance.
Here’s a look at five of the most expensive free agency busts in NFL history.
1. Deshaun Watson: Browns (2022)
- Contract: 5 years, $230 million (fully guaranteed)
- Status: Injured and underperforming
The Browns’ acquisition of Deshaun Watson was a bold move, but it has yet to pay off.
Watson has played only 19 games out of a possible 52 with the Browns organization and is currently recovering from an Achilles tendon injury that threatens the entirety of his 2025 season.
Despite a $230 million investment, the Browns have not seen the expected return on their commitment.
Especially, since the franchise took a major risk in bringing Watson back into the league after his public legal issues that sidelined him and got him suspended from the league.
Not only did the Browns take a chance on the former star QB being able to return to his previous form, despite his time away from the sport, they gave him a fully guaranteed contract.
For the NFL, this was the first contract of its kind, and after the rest of the leagues ownership has seen what happened with his failure to appear in even 50% of his possible games, it is likely that these type of deals will not be seen again for a long time, if ever.
2. Albert Haynesworth: Redskins (2009)
- Contract: 7 years, $100 million
- Outcome: Underperformed and became a locker room distraction.
Haynesworth was a dominant force with the Tennessee Titans back in the day, but failed to replicate the success he once had when he joined the Redskins.
He played only 20 games over two seasons, registering just 2.5 sacks in 2010 before being waived by the Redskins.
The deal is widely regarded as one of the worst in NFL history.
Washington still had to pay a majority of Haynesworth contract due to the options and guarantees involved, while also having to witness one of the worst declines in defensive line history.
While most may not have heard of or ever watched Haynesworth, he was a force in the league on the defensive side of the ball for years.
However, with age and injuries he declined rapidly, but was still owed the large sum.
3. Brock Osweiler: Texans (2016)
- Contract: 4 years, $72 million
- Outcome: Ineffective play led to a trade.
Osweiler’s brief stint with the Texans was marked by inconsistency.
After one season, the Texans traded him, along with a second-round pick, to the Browns to offload his contract. The move is often cited as one of the most disastrous free-agent signings.
The QB had 15 TD’s to 16 interception with Houston in his one season, showing the rest of the NFL that one solid season is not enough to pay nearly $80 million for a bench QB.
In 2015, the Denver Broncos had benched Osweiler due to again throwing more interceptions than TD passes. So, why the Houston Texans front office decided to take a benched player and pay him ~$18 million is anyone’s guess. Especially, because roughly $37 million of the contract was guaranteed.
After the trade in 2017, the Texans were on the hook to pay the same amount to Osweiler for one season of poor production that Patrick Mahomes cap hit was just last season in 2024.
Take your pick. Patrick Mahomes or Brock Oswieler. Either choice you make, if your the Houston Texans in 2017, you will end paying them both the same amount.
This should be at the top of the list but because he was a QB, the yearly salary owed to Osweiler was actually not too high. It was the guaranteed money that ruined the transaction.
4. Le’Veon Bell: Jets (2019)
- Contract: 4 years, $52.5 million
- Outcome: Limited impact and early release.
Bell’s tenure with the Jets was underwhelming. He played just 17 games over two seasons, failing to rush for 100 yards in a single game and scoring only four touchdowns.
The Jets released him midway through the 2020 season, making the contract a significant financial misstep.
At the time the deal was made, the former Steeler became the highest paid RB in the league, despite having declined in production prior to his departure from Pittsburgh. His average salary of $13.25 million, for reference, is around the same number that Nick Chubb made in 2024.
While the argument that Bell is the better back all-time compared to Chubb, his performance and age at the time made this deal essentially, ridiculous.
While we have started to see the growth in RB contracts, it is still a well known fact that a majority of Super Bowl winning teams usually have a starting RB or duo that makes less than $5 million yearly.
So, Bell being overpaid by the New York Jets is actually an understatement.
5. Nnamdi Asomugha: Eagles (2011)
- Contract: 5 years, $60 million
- Outcome: Decline in performance
The signing is often listed among the NFL’s worst free-agent acquisitions.
Asomugha was a top cornerback when the Eagles signed him, but he struggled to adapt to their defensive scheme.
His performance declined, leading to his release after two seasons.
So, paying $12 million yearly for a single defensive player, in 2011 was unheard of.
Other than the top talent at the position at the time, the average salary at the CB position was below $5 million per year.
So, paying double for a player that would have nearly no positive effect, proved at the time why the position was seemingly “underpaid”.
Risks
These signings serve as cautionary tales for NFL teams navigating the complexities of free agency.
While high-profile acquisitions can elevate a franchise, they also carry significant risks.
The sport of Football at the end of the day still ends with the bottom line, and everyone from players to ownership are in the field of play.
Next Reads
- How NFL Signing Bonuses are Structured
- T.J. Watt’s 3-Year, $123 Million Contract Extension
- Cam Ward’s Rookie Contract with the Tennessee Titans
- Garrett Wilson’s $130 Million Contract with the New York Jets
- Travis Hunter’s Rookie Contract with the Jacksonville Jaguars
Credits
Written by: Aidan Anderson
Research and Analysis: Apostle Sports Media LLC
Sources: Spotrac, OverTheCap, NFLPA reports, ESPN, CBS Sports, The Athletic, NFL team cap sheets, APSM Proprietary Analysis.
Featured Image: Public Domain / Wiki Commons
Disclaimer: This article contains general financial information for educational purposes and does not constitute as professional advice.
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