10 Worst NFL Trades in History, Ranked

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The history of the NFL cannot be told without the notion of the trade; the exchange of one non-monetary good for another among franchises.

While trades were relatively rare prior to the 1990s, they now dominate much key offseason and early regular season chatter prior to the trade deadline.

With that deadline coming up on November 5, let’s remember the worst trades in NFL history.

Here’s Heavy’s ranking of the Top 10:

10. Ricky Williams: New Orleans Saints

GettyRicky Williams.

One of the most famous trades in NFL history, known more for the headline grab than the actual contents contained within it. New Orleans shocked the league when they traded up to the fifth overall pick in exchange for the entirety of their picks in the 1999 draft — minus their second-rounder that had already been traded for receiver Eddie Kennison — and their first and third picks in the 2000 draft. While Williams was hardly a total failure, he never hit the heights that were expected of him as a Top 5, trade-everything-for-him draft pick. The Saints did manage to eventually shift him to the Dolphins for multiple good draft picks, but this is still a historically poor pick, especially when you consider the Williams’ selection was sandwiched between Hall of Famers Edgerrin James, Champ Bailey and likely future Hall of Famer Torry Holt.

9. Mohamed Sanu: New England Patriots

GettyMohamed Sanu Sr.

A lesser known trade, given both the relative anonymity of former Atlanta Falcons receiver Mohamed Sanu and the not-exorbitant compensation given up in exchange for him — just a second-round pick in that upcoming draft (2020). Yet it still undoubtedly goes down as one of the poorest trades made over the past three decades of major pro football trading, and arguably the worst exchange of head coach Bill Belichick’s career. Sanu managed just 207 yards in just over half a season with the Patriots, recording just a single touchdown, and was unsurprisingly released the following September.

8. Mitchell Trubisky: Chicago Bears

GettyMitchell Trubisky.

Although they only gave up two third-round picks to the San Francisco 49ers in this trade, the Bears get heavily penalized for missing out on what could have been. Those two picks allowed Chicago to move up a singular spot in the 2017 NFL Draft and select Mitchell Trubisky, who, despite reaching a Pro Bowl in 2018, was never close to being the Windy City’s franchise quarterback. Not only does it seem unlikely in retrospect that any other team were trying to leapfrog the Bears, but a certain three-time Super Bowl champion and two-time NFL MVP, Patrick Mahomes, was lurking on the board. Big “what if” moment for the Chicago Bears.

7. Trent Richardson: Indianapolis Colts

GettyTrent Richardson.

One of the rare cunning moves from the pre-2019, post millennium Cleveland Browns. After being drafted with the No. 2 overall pick in 2012, Richardson had a strong, if unspectacular, debut season, rushing for 950 yards — although he did record an impressive 11 touchdowns on the ground. Wanting to maximize Alabama back’s value, the Browns traded him to the Colts midway through the 2013 campaign. With clear-cut Super Bowl ambitions under sophomore franchise quarterback Andrew Luck, and down their starting RB Vick Ballard, this seemed like a win-win scenario. Indianapolis eventually gave up a first-round pick for Richardson, who, with poor play, off-the-field issues and bad injury luck, was waived after just a year and a half with the team in March 2015 — and would never play in the NFL again.

6. Russell Wilson: Denver Broncos

GettyRussell Wilson.

The trade that had many believing the Broncos “fleeced” the Seahawks ended up becoming the total opposite after everything panned out. The Seahawks were considered foolish for letting Wilson, a quarterback still considered to be in his prime years — then just 33 years old — be traded for only two first-round picks, two second-round picks, defensive lineman Shelby Harris, impressive tight end Noah Fant, and quarterback Drew Lock. In exchange, the Broncos received a quarterback unable to perform at a level that resembled his peak, although he did improve in his second year under Sean Payton — but not enough for them to not cut him during the 2024 offseason. Not a good move by GM George Paton.

5. Hershel Walker: Minnesota Vikings

GettyHershel Walker circa 1985.

Labeled “The Great Train Robbery” by Cowboys head coach Jimmy Johnson, this ultimately very one-sided trade ended up ushering in a new era of “trading mania” that we have to this day. Star tailback Hershel Walker was traded from the rebuilding Dallas Cowboys to the high-flying Vikings during the 1989 season, for a multitude of players and picks, including numerous first- and second-rounders, most of them used to draft and develop players that ultimately led them to three Super Bowls championships from 1993-6. Walker, on the other hand, failed to recapture the form that lead him to consecutive Pro Bowls in 1997-88, and failed to attain more than 850 rushing yards in his subsequent 2.5 years in Minnesota, eventually signing with the Philadelphia Eagles in 1992.

4. Bryce Young: Carolina Panthers

GettyBryce Young.

Simply the fact that Young’s story is not finished is perhaps the greatest saving grace to this trade. But as it stands now, things do not look good. The Panthers gave up two first-round picks two second-round picks and ultra valuable Pro Bowl wide receiver DJ Moore in order to move up to first in the 2023 NFL Draft. Had Carolina decided to draft fellow 2023 classmate, Ohio State QB CJ Stroud, who has had a fantastic start to his time in the league, things could have looked significantly different. Yet, Young has been quite possibly the worst quarterback in the NFL since entering, failing to perform under successive “quarterback whisperer” head coaches in Frank Reich and Dave Canales. As was seen during his time in college, Young is evidently talented, but unless something drastically changes, it will be unlikely that this trade ends up working positively for the Panthers long term.

3. Trey Lance: San Francisco 49ers

GettyTrey Lance.

Three first-round picks for a quarterback with just 17 starts — the equivalent of just one NFL season — in college: the warning signs were there all along. Dazzled by Lance’s dual threat capabilities and impressive arm talent, 49ers head coach Kyle Shanahan and general manager John Lynch decided to move from No. 12 to No. 3 in the 2021 NFL Draft, giving up three first-round picks and a third-rounder over the next three drafts. Lance sat his first year behind incumbent Jimmy Garoppolo and had his second season cut short by a season-ending ankle injury. However, a lack of vision and slow processing ability proved he was not yet ready to start at the pro level, leading to seventh-round sensation Brock Purdy taking the reins, while Lance was traded to the Cowboys for a fourth-round pick — where he has not started since.

2. Ryan Leaf: Los Angeles Chargers

GettyRyan Leaf.

One of the biggest draft busts ever, the Indianapolis Colts very much had a sliding doors moment when they chose first ballot Hall of Famer Peyton Manning over the also highly touted quarterback prospect Ryan Leaf. Sadly for the Chargers, they did not get a choice in the matter and were set on selecting a quarterback, and gave up two first-round picks and a second-rounder in exchange for the second-overall pick — moving just one spot up — in the 1998 NFL Draft, selecting Leaf. Leaf’s major off-the-field issues including criminal charges, alongside some untimely injuries, ultimately led to his failure as a professional footballer. The Washington State alum ended up going 4-14 as a starter for the Chargers before being released after the 2000 season.

1. Deshaun Watson: Cleveland Browns

GettyDeshaun Watson.

This one should be somewhat self-explanatory. Not only did the Browns give up three first-round picks, a third- and two fourth-rounders (while giving up a sixth-rounder) for a man accused of sexual misconduct by over four dozen women, but they proceeded to subsequently give him a 5 year, $230 million dollar deal that was, for the first time in NFL history, fully guaranteed. Despite all of his legal issues and him sitting out the entirety of the 2021 season, the Browns felt comfortable giving up everything to give their team a shot at a Super Bowl. And while Watson was regarded by many as a Top 5 NFL QB during his time in Houston, this was not the case in Cleveland, and the trade backfired remarkably. Poor showings in the back end of the 2022 season followed by a mediocre 2023 that was cut short by injury were then succeeded by an atrocious 2024 year in which the Browns started 1-6, only for Watson to tear his ACL in Week 7, ruling him out for the remainder of the season. A startlingly bad trade for a number of reasons, and one that will go down as the worst in the history of pro football.

The list isn’t over yet! See our pick for Number 11 HERE. Sound off to let us know who we missed!