The 13 Biggest NFL Free Agency Flops Ever

The NFL is littered with storybook free agency trades that almost single-handedly transformed a team's fortunes, resulting in Super Bowl glory. Yet, navigating the NFL free agency market is like playing a high-stakes poker game, where franchises have gambled millions on a player, leading to some truly devastating flameouts. 

Whether it's chasing marquee names, overpaying based on previous form, or banking on players believed to be past their best, be it to shore up gaps in the roster or compensate for a lack of top draft picks, while some signings fail silently, others become humiliating, not to mention expensive, busts.

As a result, we've ranked the all-time 13 worst free agent deals in NFL history where high expectations were met with abject locker-room failures.

What makes a free agency signing “bad”?

Let's face it, the incentives are huge in mastering the NFL free agency. Recent history has demonstrated this when the likes of Payton Manning and Drew Brees seemingly reenergized the Broncos and Saints organizations - but when it goes wrong, it can go horribly wrong. 

At its core, a bad signing is more than just a player not meeting expectations; it’s also about the longer-term consequences of crippling salary cap commitments that can impact a team for years to come. Beyond players being unable to recreate the form of old, issues such as injuries, sizeable off-field distractions, or simply the inability to adjust to a new system also come into play, as seen here.

The 13 worst free agent signings in NFL history

#13: Allen Robinson (WR)– Los Angeles Rams, 2022

For Allen Robinson, his initial move to the Rams in 2022 generated a huge degree of excitement on the back of him registering back-to-back 1,000-yard seasons with the Bears before becoming a free agent. Having signed the dependable receiver in a $46.5 million deal, the Super Bowl champions believed Robinson would ultimately add a new dimension to their potent passing game. Unfortunately for HC McVay, he lacked cohesion with his own offensive playcalling. Then he required season-ending surgery just 10 games into his Rams career, after which Robinson was traded to the Steelers after just one season.

#12: DeMarco Murray (RB) – Philadelphia Eagles, 2015

After being named NFL Offensive Player of the Year in 2014, DeMarco Murray opted to join the Eagles in 2015, with HC Chip Kelly being heralded for securing the services of the league's leading rusher. As a result, Philadelphia handed the ex-Cowboy RB a five-year, $42 million contract, anticipating his rich form would bolster their already dominant offense. Nonetheless, unable to replicate his previous form, Murray also struggled to gel in Chip Kelly's offense and was traded to the Titans at the end of the 2015 season, where, ironically, he returned to form, securing his third Pro Bowl call-up the following season.

#11: Randy Gregory (LB) – Denver Broncos, 2022

Choosing to turn down a generous contract extension with the Cowboys, star linebacker Randy Gregory instead went for a lucrative five-year, $70 million contract offered by the Broncos during the 2022 free agency. After suffering a knee injury in Week 4, Gregory then missed the majority of the season, only returning in Week 15 for the last two games. The following season, he didn't fare much better and was benched in Week 3 by new head coach Sean Payton, who traded him to the 49ers in October after he had played only 10 games for the Broncos.

#10: Nnamdi Asomugha (CB) – Philadelphia Eagles, 2011

Widely regarded as the best free agent on the market in 2011, the Eagles snapped up cornerback Nnamdi Asomugha in the hope of fortifying a flailing defense. Signing a five-year, $60 million deal, Asomugha suffered the ill fate of working under offensive line coach turned defensive coordinator Juan Castillo's system, which was wholly unsuited to Asomugha's skill set. Despite playing in every game in his first two seasons, Asomugha was released by the Eagles at the end of the 2012 season after refusing to agree to the renegotiated terms of his contract. Asomugha was subsequently voted the second-most-hated player in the franchise’s history.

#9: Nick Foles (QB) – Jacksonville Jaguars, 2019

Nick Foles’ 2019 signing with Jacksonville was on the back of his Super Bowl MVP performance in Philadelphia, which made the deal look like a steal when they offered him a four-year contract worth $88 million. Expected to be a long-term solution to Jacksonville’s QB woes, Foles managed to break his left clavicle in the first quarter of the opening game of the season, returning for three more games in Week 11 before being benched in favor of rookie Gardner Minshew. Foles was hastily traded to the Bears in the postseason, having played only four games for the Jags.

#8: Brock Osweiler (QB) – Houston Texans, 2016

After showing flashes of genuine talent having backed up Payton Manning in Denver, Houston jumped at the chance to sign Brock Osweiler as a free agent in 2016. Signing a four-year $72 million contract, the front office and fans alike firmly believed they had landed their future franchise quarterback. Everything looked positive after he led the Texans to a 3-1 start, but it didn't last long as Osweiler went on to set a single-season franchise record by throwing 16 interceptions in his debut season. Despite reaching the NFL playoffs, the decision was made to trade him to the Cleveland Browns after just one season, along with two additional draft picks to help offset the expense of Osweiler's cap hit.

#7: J.C. Jackson (CB) – Los Angeles Chargers, 2022

Another franchise to suffer a catastrophic Pro Bowl free agent signing was the Los Angeles Chargers, who poached J.C. Jackson with a five-year, $82.5 million deal. As one of the league's top corners, LA had hoped Jackson was the missing piece in their otherwise solid secondary. Still, things didn't start well, having to undergo ankle surgery in the offseason, he missed the entire preseason and the season opener as a result. After a Week 2 debut loss to the Chiefs, Jackson made four more starts before suffering a season-ending injury, which led to his eventual trade in October 2023 back to his first team, the Patriots, with just seven games to his name.

#6: Ja'Wuan James (OT) – Denver Broncos, 2019

Another Broncos bust on the list of the worst free-agent signings was the acquisition of veteran offensive tackle Ja'Wuan James to stabilize Denver's sack-prone offensive line. Having given James a four-year, $51 million contract, he suffered a knee injury in Week 1 and missed the majority of the season while recovering. After opting out of playing in 2020 during the COVID pandemic, James then tore his Achilles tendon in the following postseason and was promptly released, having only played three times for the franchise.

#5: Byron Maxwell (CB) – Philadelphia Eagles, 2015

As an instrumental figure in Seattle's legendary Legion of Boom and with a Super Bowl victory under his belt, Byron Maxwell was poised to be the superstar cornerstone of the Eagles' secondary in 2015. Having announced he was the first choice cornerback after signing his six-year, $63 million contract, Maxwell suffered a torrid time throughout the season. Seemingly unable to replicate his form while adapting to DC Billy Davis' defensive setup, Maxwell’s short-lived career in Philly ended when he was unceremoniously traded to the Miami Dolphins the following offseason.

#4: Christian Wilkins (DT) – Las Vegas Raiders, 2024

Christian Wilkins was on an upward trajectory after five prolific seasons with the Miami Dolphins, and on the back of a career-high nine sacks in 2023, he was picked up as a free agent in March 2024 by the Las Vegas Raiders. Signing a $110 million, four-year contract, Wilkins started quickly before being sidelined for the season with a foot injury in Week 5. Following a postseason dogged by the perception that Wilkins was not taking his rehabilitation seriously, the Raiders eventually released the former Dolphin and sought to claw back $35.2 million of his guaranteed salary, meaning he secured a $49.7 million paycheck for playing just five games as a Raider.

#3: Deion Sanders (CB) – Washington Commanders, 2000

An elite player on both sides of the ball, Deion Sanders was surprisingly released by the Dallas Cowboys in a salary-cap restructuring in June 2000, which subsequently saw Washington beat several teams to the eight-time Pro Bowler's signature. The two-time Super Bowl winner agreed to a seven-year, $56 million contract and hit the ground running, posting impressive defensive stats throughout the season. Unfortunately, Washington missed the playoffs with an 8-8 record. However, leading up to training camp the following season, Sanders abruptly retired in 2001, and while forfeiting part of his deal payment, the sizable free agent deal took a huge chunk out of Washington's cap in 2001 and 2002.

#2: Kirk Cousins (QB) – Atlanta Falcons, 2024

A more recent addition to the shortlist, Kirk Cousins' free agency deal with the Atlanta Falcons certainly registered high on the biggest NFL free agency flops of all time. After originally signing Cousins up on a four-year, $180 million deal, they then immediately drafted QB Michael Penix Jr. as the eighth overall pick in the draft. A mediocre season ensued with Cousins as the starter and ended up leading the NFL in interceptions before being benched in Week 16 in favor of the rookie. Cousins' second season in Atlanta didn't fare much better - starting as back-up quarterback until Penix Jr. was injured in Week 11 – before being released under a restructured deal by the Falcons in March 2026.

#1: Albert Haynesworth (DT) – Washington, 2009

Undoubtedly, the worst NFL free agency bust of all time again traces back to Washington, which signed the highly sought-after first-team All-Pro defensive tackle at the time, Albert Haynesworth. Nonetheless, it didn't take long for the cracks to appear as Haynesworth could not replicate his form from his time in Tennessee, appearing unable, or as some claim, unwilling to adapt his game to DC Greg Blache's schemes. Haynesworth's turbulent stint in Washington continued to unravel, refusing to take part in offseason workouts in 2010 before failing a basic fitness test on returning to training camp. Traded midway through the 2010 season - not long after Haynesworth appeared to give up mid-play in a game against the Giants - Washington was left to swallow the huge dead cap hit as a result, cementing its status as the worst NFL free agency deal ever made.

The consistent themes behind free agency busts

Certainly, there’s not much room for error when teams look to recruit players during free agency. Nail it, and they can reverse the fortunes of a failing franchise, get it horribly wrong, and a bad deal can single-handedly tie up their NFL salary cap for seasons to come.

That said, with so many inherent risks, teams are forced to bid competitively based on a player’s potential, offsetting the pitfalls of possible injury, poor performances, a lack of coaching chemistry, and, in extreme cases, an unwillingness to play. Ultimately, elite talent, top-ranked stats, and frequent Pro Bowl appearances are the currency that drives free agency trades, yet, as this shortlist of free agency busts shows, they offer absolutely no guarantee of future performance.

Conclusion

For teams and fans alike, every NFL free agency period beckons a renewed sense of optimism, of either strengthening a poor roster or simply plugging gaps in an already dominant offensive or defensive unit. Regardless, as this list of the 13 biggest NFL free agency busts of all time shows, the reality is that even securing the services of a Super Bowl-winning talent can turn into a financial disaster.

Of course, this year’s NFL free agent frenzy may very well produce a key player acquisition capable of becoming an inspirational catalyst in leading a team to Super Bowl victory. But let’s be real – in today's game, the odds of a brand-new entry being added to this notorious list of free agency NFL flops seem a far more likely prospect.