5 Worst trades in NFL history

NFL teams often use the trade market in an attempt to improve their rosters. While it's important to be aggressive in the pursuit of superstar players, it can, sometimes, backfire in a big way. There have been many times in NFL history where a team has overpaid in a trade that ended up being a disaster for them in the end. Here are the five worst ones of all time.

5 Worst NFL trades of all time

#5 - San Diego Chargers trade up one spot to draft Ryan Leaf

San Diego Chargers quarterback Ryan Leaf

The San Diego Chargers decided they needed a quarterback in the 1998 NFL Draft. They were the third pick in a draft that featured Peyton Manning and Ryan Leaf, two highly-rated quarterback prospects. To make sure they can get one of them, the Chargers traded away three draft picks and two players to the Arizona Cardinals to move up one spot in the draft.

The move ended up being a disaster as Ryan Leaf turned out to be one of the biggest draft busts of all time. He posted just a 4-17 career record with 14 touchdowns and 36 interceptions.

#4 - Houston Texans trade DeAndre Hopkins for David Johnson

Houston Texans wide receiver DeAndre Hopkins

General manager and head coach Bill O'Brien made many questionable decisions during his time in charge of the Houston Texans. None of them were as bad as the trade he made during the 2020 NFL season that made no sense from the very moment it happened.

O'Brien sent superstar wide receiver DeAndre Hopkins, one of the best players in the entire league at the time, to the Arizona Cardinals for aging running back David Johnson, who had been on the decline for several years. The trade was one of the final moves O'Brien made before being fired.

Ranking the 5 worst trades in NFL history

#3 - New Orleans Saints trade away 8 draft picks to select Ricky Williams

New Orleans Saints running back Ricky Williams

The New Orleans Saints entered the 1999 NFL Draft in search of a new running back. They fell in love with Ricky Williams, one of the highest-rated running back prospects of all time. The Saints decided they would do whatever was necessary to land their coveted running back Williams.

While being aggressive to acquire a target is important, it's equally necessary to make sure to avoid overpaying. The Saints didn't balance these two concepts as they gave up an insane package to move up in the draft to select Williams. They sent eight total draft picks to Washington, including two first-rounders, a second and two third-round picks.

#3 - Chicago Bears trade up one spot to draft Mitchell Trubisky

Chicago Bears draft Mitchell Trubisky

The Chicago Bears made a head-scratching move during the 2018 NFL Draft when they traded up just one spot to select Mitchell Trubisky. The move was considered a reach at the time, and it didn't appear necessary at all to trade up, if Trubisky was their desired target. The Bears surrendered four draft picks to execute the trade.

What made the trade even worse, in hindsight, was who they passed on at quarterback in favor of Trubisky. Superstar quarterbacks Patrick Mahomes and Deshaun Watson were each selected shortly after him, making the trade an absolutely disastrous decision for the Bears.

#1 - Minnesota Vikings trade a fortune for Herschel Walker

Minnesota Vikings running back Herschel Walker

Jerry Jones purchased the Dallas Cowboys in 1989. In 1990, he traded away NFL superstar Herschel Walker. While trading away one of the most talented players in the NFL is shocking, it's not as wild as what the Minnesota Vikings gave them in return. The Cowboys received an insane package of five players and eight draft picks, including three first-round picks and three second-rounders.

While Walker lasted just two seasons with the Vikings and failed to eclipse 1,000 yards in either of them, the Cowboys were able to build a dynasty with their haul. They used the picks to select legends like Emmitt Smith and Darren Woodson while building one of the best rosters in NFL history. The Cowboys would go on to win three Super Bowl rings in the 1990s.