Top 10 Worst Trades in NFL History

The National Football League (NFL) has seen its fair share of impactful trades over the years, some of which have shaped the fortunes of franchises for years to come.

Here, we take a closer look at the top 10 worst trades in NFL history, examining the impact of each trade and the reasons behind their inclusion on this list.

1. Herschel Walker Trade (1989)

The trade involving Herschel Walker stands as one of the most lopsided deals in NFL history. The Dallas Cowboys sent Walker, along with several draft picks, to the Minnesota Vikings in exchange for a bounty of players and draft picks.

This trade provided the foundation for the Cowboys' dynasty of the 1990s, as they used the acquired assets to build a championship-winning team.

The Vikings, on the other hand, struggled to find success in the aftermath of this trade, making it a clear candidate for the worst trade in NFL history.

2. Ricky Williams Trade (1999)

In 1999, the New Orleans Saints traded their entire 1999 draft and their first- and third-round picks in 2000 to the Washington Redskins to move up to the fifth overall pick and select Ricky Williams.

This trade heavily depleted the Saints' future draft capital and failed to yield the expected returns, as Williams' tenure with the team was marred by inconsistency and off-field issues.

The Redskins, meanwhile, used the acquired picks to bolster their roster, making this trade a significant setback for the Saints.

3. Eric Dickerson Trade (1987)

The trade that sent Eric Dickerson from the Los Angeles Rams to the Indianapolis Colts in 1987 is often cited as one of the worst in NFL history.

The Rams received a package of draft picks and players in return, but none of the acquired assets could match Dickerson's impact on the field.

Dickerson continued to excel with the Colts, while the Rams struggled to fill the void left by his departure, making this trade a regrettable move for the Rams.

4. Jay Cutler Trade (2009)

In 2009, the Denver Broncos traded quarterback Jay Cutler to the Chicago Bears in exchange for a package that included quarterback Kyle Orton and several draft picks.

Cutler's departure left a significant void at the quarterback position for the Broncos, while his tenure with the Bears failed to live up to expectations.

The Broncos' inability to adequately replace Cutler compounded the impact of this trade, earning it a place among the worst in NFL history.

5. Trent Richardson Trade (2013)

The Cleveland Browns' decision to trade running back Trent Richardson to the Indianapolis Colts in 2013 in exchange for a first-round draft pick raised eyebrows across the league.

Richardson failed to make a significant impact with the Colts, while the first-round pick the Browns received did not translate into a franchise-altering talent.

6. Joey Galloway Trade (2000)

The trade that sent wide receiver Joey Galloway from the Seattle Seahawks to the Dallas Cowboys in 2000 is often regarded as one of the most lopsided deals in NFL history. The Cowboys parted with two first-round draft picks to acquire Galloway, who failed to live up to the expectations in Dallas. The Seahawks, on the other hand, used the acquired picks to bolster their roster, making this trade a significant setback for the Cowboys.

7. Jon Gruden Trade (2002)

In 2002, the Oakland Raiders traded head coach Jon Gruden to the Tampa Bay Buccaneers in exchange for a package including multiple draft picks and cash.

This trade was heavily criticized as the Buccaneers, under Gruden's leadership, went on to win the Super Bowl the following season, while the Raiders struggled to find sustained success. 

8. Carson Palmer Trade (2011)

The Cincinnati Bengals' decision to trade quarterback Carson Palmer to the Oakland Raiders in 2011 in exchange for a first-round pick and a conditional second-round pick failed to yield the desired returns for both teams.

Palmer's tenure with the Raiders was marred by inconsistency, while the Bengals struggled to find a suitable replacement at quarterback. 

9. Roy Williams Trade (2008)

The trade that sent wide receiver Roy Williams from the Detroit Lions to the Dallas Cowboys in 2008 stands as one of the most regrettable deals in NFL history.

The Cowboys parted with multiple draft picks to acquire Williams, who failed to make a significant impact in Dallas.

The Lions, on the other hand, used the acquired picks to replenish their roster, making this trade a significant setback for the Cowboys.

10. Steve Largent Trade (1976)

The trade that sent wide receiver Steve Largent from the Houston Oilers to the Seattle Seahawks in 1976 is often cited as one of the worst in NFL history.

The Oilers received an eighth-round draft pick in return, a paltry return for a future Hall of Famer.

Largent went on to have a storied career with the Seahawks, while the Oilers struggled to find a receiver of his caliber, making this trade a significant setback for the franchise.

All in all, the NFL has witnessed several trades that have had far-reaching implications for the franchises involved.

The trades listed above stand out as some of the worst in NFL history due to their lopsided nature or the failure to yield the expected returns. 

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