The NFL has seen its fair share of blockbuster trades, but not all of them pan out as expected. While some teams have walked away as clear winners, others have been left picking up the pieces after a deal went horribly wrong.
Whether due to injuries, poor performance, or simply giving up on a player too soon, these 15 trades stand out as some of the biggest disasters in league history.
1. Herschel Walker to the Vikings (1989)
The Dallas Cowboys sent Herschel Walker to the Minnesota Vikings in a trade that is now considered one of the most lopsided in NFL history. In return, Dallas received a haul of draft picks that helped build their 1990s dynasty, including Emmitt Smith. Meanwhile, Walker failed to make the impact the Vikings had hoped for, leading to one of the biggest backfires ever.
2. Ricky Williams to the Saints (1999)
The New Orleans Saints, led by head coach Mike Ditka, traded away their entire draft class (and future picks) to acquire running back Ricky Williams from Washington. Williams had an up-and-down career in New Orleans before moving on to Miami, while the Saints struggled to recover from mortgaging their future.
3. Jay Cutler to the Bears (2009)
The Chicago Bears traded a package of draft picks and quarterback Kyle Orton to the Denver Broncos for Jay Cutler. Though Cutler had his moments, he never lived up to his elite potential, struggling with inconsistency and never delivering the franchise-changing success the Bears had hoped for.
4. Trent Richardson to the Colts (2013)
In desperate need of a running back, the Indianapolis Colts traded a first-round pick to the Cleveland Browns for Trent Richardson. Unfortunately, Richardson never lived up to the hype, averaging just 3.1 yards per carry with the Colts before quickly fading out of the league.
5. Antonio Brown to the Raiders (2019)
The Oakland Raiders traded for Antonio Brown, expecting him to be their No. 1 wide receiver. However, a series of off-the-field issues—including a helmet dispute, frostbitten feet, and public feuds—led to his release before he even played a single game for the team.
6. Sam Bradford to the Eagles (2015)
The Philadelphia Eagles acquired Sam Bradford from the Rams in exchange for Nick Foles and draft picks. While Foles would go on to win a Super Bowl with the Eagles later, Bradford’s time in Philly was short-lived, leading to another trade just a year later.
7. Carson Palmer to the Raiders (2011)
After a standoff with the Cincinnati Bengals, Carson Palmer was traded to the Oakland Raiders for a first-round pick. Palmer was far from elite in Oakland, and the trade cost the Raiders valuable draft capital without yielding much success.
8. DeAndre Hopkins to the Cardinals (2020)
The Houston Texans inexplicably traded All-Pro wide receiver DeAndre Hopkins to the Arizona Cardinals for running back David Johnson and a second-round pick. Hopkins continued to be dominant, while Johnson struggled, leading to the eventual firing of head coach Bill O’Brien.
9. Percy Harvin to the Seahawks (2013)
The Seattle Seahawks traded multiple picks for Percy Harvin, expecting him to be a game-changer. While he did contribute in the Super Bowl, injuries and off-the-field issues limited his impact, and Seattle quickly moved on.
10. Brandon Marshall to the Dolphins (2010)
The Miami Dolphins sent two second-round picks to the Denver Broncos for Brandon Marshall, expecting him to be a top-tier wide receiver. However, he lasted just two seasons before being traded again, never reaching his peak in Miami.
11. Deshaun Watson to the Browns (2022)
The Cleveland Browns made a massive gamble by trading multiple first-round picks to the Houston Texans for quarterback Deshaun Watson, despite his off-field legal issues. Cleveland then signed him to a record-breaking fully guaranteed $230 million contract. Watson’s tenure with the Browns has been marred by injuries, suspensions, and inconsistent play, making this one of the most questionable trades in NFL history.
12. Roy Williams to the Cowboys (2008)
The Dallas Cowboys sent multiple draft picks, including a first-rounder, to the Detroit Lions for wide receiver Roy Williams. Williams never lived up to expectations, and the Cowboys later regretted giving up so much for a player who failed to produce.
13. Joey Galloway to the Cowboys (2000)
The Cowboys traded two first-round picks to the Seahawks for wide receiver Joey Galloway, hoping he would replace Michael Irvin. Unfortunately, Galloway tore his ACL in his first game with the Cowboys and never became the impact player they had hoped for.
Read More: 20 NBA Trades That Left Fans Stunned and Speechless
14. Khalil Mack to the Bears (2018)
The Chicago Bears traded multiple first-round picks for star pass rusher Khalil Mack, but despite his individual success, the move didn’t translate into long-term team success. The Bears struggled offensively, and Mack was eventually traded to the Chargers. Meanwhile, the Raiders used the picks to rebuild.
Read More: The 10 Worst Number 1 Draft Picks in NFL History
15. Brock Osweiler to the Browns (2017)
The Houston Texans essentially paid the Cleveland Browns to take Brock Osweiler off their hands, including a second-round pick just to dump his contract. Osweiler never played a snap for Cleveland, making the whole ordeal a bizarre and costly mistake.
Read More: The 18 Most Questionable Trades in Sports History
