The 9 Most Regrettable Free Agency Signings In NFL History

There are plenty of NFL teams who’ve gotten a major boost by signing a player whose talents were up for grabs as a free agent, but there’s no guarantee they’re going to be able to live up to expectations after the contract is inked.

NFL teams obviously devote a ton of time and effort to making sure they’re not going to end up regretting the decision to sign a free agent, but there’s only so much you can do to predict what’s going to unfold once you add them to the roster.

There are plenty of franchises that made a splash with a big signing in free agency that ultimately failed to pan out like they’d hoped, but it’s hard to top these ones that backfired in a big way.

Albert Haynesworth—Washington

Albert Haynesworth was a force to be reckoned with during the bulk of the seven seasons he spent with the Titans, and the team that’s now known as the Washingon Commanders was hoping the defensive tackle would have the same impact when they signed the man who was coming off of back-to-back Pro Bowl seasons to a seven-year contract worth $100 million in 2009.

Unfortunately, that did not end up being the case. Haynesworth publicly butted heads with the team’s coaching staff over their defensive schemes. failed to pass a fitness test after arriving at training camp in 2010, and was benched for the last four games of the season after internal drama continued to unfold.

He only spent two years in Washington before being traded to the Patriots ahead of the 2011 campaign for a similarly ill-fated stint that ended when he got into it with a coach during a game. He got one last chance with the Buccaneers after being released midway through the year, and his NFL career came to an end after he was released at the end of the season.

David Boston—Chargers

David Boston lived up to the hype that led to the Cardinals selecting him with the eighth overall pick in the 1999 NFL Draft to kick off a four-year stint in Arizona, and the Chargers made a splash when they signed him to a seven-year contract worth up to $42 million in 2003 (although only $12 million was guaranteed).

He did haul in 70 catches while recording 880 yards and seven TDs during his first (and only) year in San Diego, but as was the case with Haynesworth, it was marred by disagreements with coaches that eventually led to him being suspended for a game.

The Chargers ultimately decided Boston wasn’t worth the headache, and he was traded to the Dolphins before his career came to a quiet end due to a knee injury he was never able to fully recover from.

 

Jeff Garcia—Browns

The quarterback position has been a notorious revolving door for the Browns since the franchise returned from its three-year hiatus at the turn of the millennium, and Jeff Garcia is just one of the dozens of players who’ve gone through it.

Garcia was named to the Pro Bowl three seasons in a row during his time with the 49ers. However, he had an off year in 2003 that led to San Francisco opting to release him, and the Browns subsequently gave him a four-year, $25 million deal.

That ill-fated experiment lasted a grand total of one year, as Cleveland decided to go in a new direction after a disappointing season where he only appeared in 11 games while throwing for 1,731 yards while recording just 10 touchdowns and nine interceptions.

Nnamdi Asomugha—Eagles

Nnamdi Asomugha kicked off his NFL career with the Eagles and cemented himself as one of the best CBs in the league during the eight years he spent in Oakland.

The Eagles had high hopes when they secured one of the most sought-after names in the class of free agents that hit the market in 2011 with a five-year, $60 million contract.

He may not have experienced a precipitous decline as far as his individual stats were concerned, but he was the most notable member of an infamously porous Eagles secondary that was routinely torched during the two seasons he spent in Philadelphia before being released.

DeMarco Murray—Eagles

The Asomugha signing wasn’t the only big swing-and-a-miss the Eagles front office fell victim to in the 2010s, as Philly also had some regrets after signing DeMarco Murray to a five-year, $42 million deal to fill the void that formed after trading LeSean McCoy to the Bills in 2015.

Murray was coming off of a season where he earned Offensive Player of the Year honors after leading the NFL in rushing with the 1,845 yards he racked up with the Cowboys while averaging 4.7 per carry.

Unfortunately, he didn’t even come close to sniffing that number during his first and only year with the Eagles, who traded him to the Titans after he ran for just 702 yards and only averaged 3.7 per attempt.

Antonio Brown—Patriots

Based on the drama that unfolded during his time with the Steelers and Raiders, the Patriots had to know what they were signing up for when they offered Antonio Brown a one-year, incentive-filled deal worth up to $15 million (which was also accompanied by a $9 million signing bonus).

It’s very safe to say that gamble did not pay off, as Brown appeared in a single game while recording four catches for 56 yards before he was released in the wake of the abuse and assault allegations levied against him by a former trainer.

New England attempted to withhold the bulk of the money it had promised to pay him, but it was ultimately forced to fork over $5 million after agreeing to a settlement—which means it paid him more than $1 million for each pass he snagged.

Le'Veon Bell—Jets

Speaking of guys who were surrounded by drama during their time with the Steelers before seeing things take a turn for the worse after finding a new home…

Le’Veon Bell refused to suit up for the Steelers in 2018 after sitting out what would end up being his final season in Pittsburgh, and the Jets pounced on the chance to sign him before he inked a four-year, $52.5 million contract (Todd Gurley was the only RB in the NFL being paid more at the time).

Bell ran for 1,291 yards (averaging 4 per carry) and had a total of 11 touchdowns (nine rushing and two receiving) during his last year in action for the Steelers, but he only posted 789 yards (3.2 carry) and 3 TDs after returning from his hiatus.

He only appeared in two games the following year before liking a tweet about being traded in October, which sparked some drama that led to him being released just a couple of days later.

Neil O'Donnell—Jets

Neil O’Donnell spent five seasons in Pittsburgh, but his time with the Steelers came to a disastrous end after he threw three interceptions during the team’s loss to the Cowboys in Super Bowl XXX.

Those red flags didn’t stop the Jets from giving him a five-year, $25 million contract ahead of the 1996 season, but the team got off to a 0-6 start during a stretch where he threw just four TDs compared to seven interceptions prior to suffering a season-ending shoulder injury.

He got another shot the following year and bounced back by throwing 17 TDs and seven picks while starting almost every game. However, Glenn Foley earned the starting role ahead of the 1999 campaign, and the Jets released O’Donnell after he declined to restructure his contract.

Desmond Howard—Raiders

This one requires a little bit of context, as Desmond Howard was a former Heisman winner who made a name for himself as a return specialist and put his talents on full display during a monster performance in Super Bowl XXXI that led to him being named the game’s MVP after his Packers topped the Patriots.

The Raiders decided to give him a four-year, $6.1 million deal in 1997—a ton of money for a roleplayer like Howard—under the assumption he’d continue to have a similar impact on the special teams front.

During his first season, his punt return production declined by more than half based on average yards and he failed to return a single one for a touchdown after taking three to the house with Green Bay the previous year (it’s worth noting he was still similarly reliable on kick returns despite his inability to convert any into a TD).

He did return a couple of punts for a TD during his second campaign, but he was cut by the team after the season before returning to Green Bay.