Top 10 worst trades in NFL history

From Deshaun Watson and Russell Wilson's bloated deals to Herschell Walker's unbelievable trade, here are the worst deals made by teams in NFL history.


Top 10 worst trades in NFL history

There have been a lot of questionable trades in the NFL in recent history (Image Credits: L-via IMAGO, C-via AP, R-via IMAGO)

In the Super Bowl Era, the game of football has been privileged enough to witness greatness in the form of different players. There has been plenty of talent in the National Football League and teams frequently keep trading for more talent in order to get better. Irrespective of how good a player is today, there is no guarantee that they will perform just as well or better tomorrow.

Every trade ends up being a bet placed by a team on a player, especially the trades made by teams, in order to secure a better position in the draft. Despite this knowledge, football teams must continue to take daring risks because if you don’t, then you stagnate and struggle to win.

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This is a list of the worst bets made in NFL history. While one or two of them were not completely on the team, the rest were structured in such a way that made fans perplexed and question their loyalty to their franchise.

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These are the 10 worst deals in NFL history:

10. Randy Moss traded to New England by the Raiders

The Oakland Raiders are responsible for creating one of the most menacing duos in football history. To date, it is hard to believe that this trade happened because the Patriots received a Ferrari for the price of a Prius.

Randy Moss
Randy Moss (Image via Open Source/X)

The Raiders realized that Randy Moss was not going to thrive in the Oakland situation and he was not putting up numbers similar to his days in Minnesota. However, rather than leveraging him to obtain a bunch of draft picks or another star in their prime, the team chose to hand him on a silver platter to the New England Patriots in exchange for a 2007 4th-round pick.

Oakland drafted John Bowie (Yes, exactly, who is that?) He played a total of five games for them in three seasons. Moss, on the other hand, hit it off with Tom Brady and broke the single-season passing and receiving touchdown record held by Jerry Rice in his first season. The only feat this duo fell short of achieving was winning a Super Bowl.

9. Wes Welker traded to New England by the Dolphins

By this point, it is clear that the Patriots are the kings of finesse, or at least they were. The team acquired one of the greatest players of their franchise via a trade with the Miami Dolphins. New England signed Wes Welker, an undrafted wide receiver after sending their 2007 second and seventh-round draft picks to Miami in 2007.

Wes Welker
Wes Welker (Image via Sports Illustrated)

While Welker continues to be chastised for his drop in the Super Bowl against the Giants that wound up costing New England a Lombardi Trophy, his greatness cannot be overlooked as. Despite a 0-4 Super Bowl record, he is revered as the greatest undrafted player of all time.

Wes Welker transitioned into one of the most reliable and consistent receivers that Tom Brady could fall to. He went on to finish his career as a 5x Pro Bowler, 2x First-Team All-Pro, 2x Second-Team All-Pro, a 3x leader in the NFL in terms of receptions and set multiple records in the Patriots franchise during his tenure there.

8. Atlanta Falcons trade Brett Favre for a first-round pick

The Falcons are accustomed to fumbling when they have something good on their hands. The trajectory of this franchise could have been different had they not chosen to trade Brett Favre after drafting him in the second round of the 1991 NFL Draft. This was because HC Jerry Glanville was adamant that he had a better shot to win with his QBs, Chris Miller and Billy Toliver.

Brett Favre
Brett Favre (Image via Open Source/X)

He was traded after his rookie year to the Packers in exchange for a first-round pick and while it looked like Atlanta won this trade as it effectively upgraded its second-round pick into a first-round pick. The quarterback they wound up trading went on to win one Super Bowl, about three NFL MVPs, and a Hall of Fame career.

On the contrary, Tony Smith, the man that Atlanta drafted after trading Favre, ended his career with 329 rushing yards and was out of the NFL by 1999.

7. Raiders acquire Antonio Brown from the Steelers

In 2019, the differences between star wide receiver Antonio Brown and the Pittsburgh Steelers organization reached a breaking point. The man forced his way out of the team and while Pittsburgh initially wound up with $21.12 in dead money and received a third and fifth-round pick from the Raiders; they came out on top of this deal.

Antonio Brown
Antonio Brown (Image via Open Source)

This is because AB went on to play 0 games for Oakland and instead his antics on and off the field worsened. His relationship with Raiders GM Mike Mayock took a turn for the worse and he got kicked off the team before the regular season started. His infamous “I’m free” celebration after finding out he was being released remains the only highlight he had with the team. Pittsburgh, on the other hand, wound up drafting receiver Diontae Johnson and tight end Zach Gentry.

Johnson had five good seasons with the Steelers and wound up becoming a role player in the team’s offense. Pittsburgh managed to get a liability off their roster and got rewarded for it.

6. Colts trade elite RB Marshall Faulk to the Rams

Marshall Faulk was at the top of his career and formed a key part of the Indianapolis Colts offense with 5.000+ rushing yards and 8,000+ total yards through five seasons with the team. However, rather than pay him, Indy felt it was best to trade him in exchange for a second-round and fifth-round pick.

Marshall Faulk
Marshall Faulk (Image via Open Source)

This bet wound up being a bad one as Faulk went on to help the St. Louis Rams build their Greatest Show on Turf offense, which ultimately won them a Super Bowl, and he went on to win an MVP award. Indianapolis’ picks in the draft were not good enough to justify this trade.

5. Bears trade up for Mitchell Trubisky in the 2017 draft

One has to feel bad for Chicago fans. You cannot make this up. The Bears needed a QB heading into the 2017 draft and they had the third overall pick but in order to have a shot at drafting Mitchell Trubisky, they moved up one pick by sending four of their picks, the first-round (3rd overall), the 67th overall, 70th overall, and 111th overall picks to the 49ers.

Mitchell Trubisku
Mitchell Trubisky (Image via Bleacher Report)

San Francisco wound up picking linebacker Fred Warner, a key piece of their defense who has been a starter since his rookie season with one of those picks and the team traded the 67th overall pick to the Saints who used it to draft, star running back Alvin Kamara.

By drafting Trubisky, Chicago gave up its chance to get Patrick Mahomes, who is now a multiple-time Super Bowl winner. In all fairness, Trubisky was not a complete bust as he did lead them to the playoffs twice.

4. Denver Broncos get John Elway from the Baltimore Colts

The Colts had the top pick in the 1983 draft. The team wanted to draft John Elway, but there was just one problem.

The quarterback had made it clear to owner Robert Irsay that he did not want to play for them. Despite his reluctance, Irsay chose Elway and then the quarterback held out, which compelled the team to trade him to Denver in exchange for Chris Hinton, Mark Herrmann, and a first-round pick in the subsequent year’s draft.

John Elway
John Elway (Image via Open Source)

John Irsay’s decision cost the Colts a chance to draft an elite quarterback in a year, which to date is considered as one of the best quarterback classes of all time. Six QBs were taken in the first round alone and two of them, apart from Elway, went on to have Hall of Fame careers. The other two are Dan Marino and Jim Kelly.

Notably, Eric Dickerson, the greatest running back of all time, was taken by the LA Rams with the second pick behind the Colts. All three players that the Colts received in exchange for John Elway fell short as they did not perform, whereas the quarterback went on to become a multiple time Super Bowl champion, MVP, and had a decorated career.

3. Seahawks trade Russell Wilson to Denver

In the last trade, Denver came out on top, but in this one, the Broncos were way off. It was a deal that was supposed to make the Mile-High City legitimate contenders to win the Super Bowl but the result, one disappointing season under a head coach that went on to be fired and another season which turned out to be Russell Wilson‘s final season there.

Russell Wilson
Russell Wilson (Image via AP)

Denver gave up Drew Lock, Noah Fant, Shelby Harris, two second-round picks, two first round picks, and a fifth-round pick for Seattle. Apart from this, the team offered him a $242.5 million deal with $85 million guaranteed. In two years, the team paid him over a $100 million just to go 11-19. Wilson was released by the Broncos after his second year, despite his dealing being for five years.

The trade is considered to be one of the worst in NFL history because of how much Denver gave up just for Wilson and a fourth round pick in 2022. Apart from this, the team continues to suffer due to the dead cap amount that plagues it even after the veteran’s departure. It cost the team an opportunity to draft fresh talent with whom they would have perhaps fared better.

2. Cowboys trade Herschel Walker to Minnesota

It is a wonder that the Dallas Cowboys were not found guilty of committing a robbery in broad daylight after this trade went through. After a phenomenal year wearing the star on his chest, running back Herschel Walker was a hot commodity sought after by many teams, but the Minnesota Vikings were the only team that went all-in on him.

Herschel Walker
Herschel Walker (Image via Open Source)

The team was convinced that he would turn their fate around and make them a Super Bowl contender. They put up an offer that was too good to be true, but even harder for the Cowboys to refuse. Minnesota practically traded away its team and future as they gave up eight draft picks and five active players in exchange for Walker and three draft picks. That is a ridiculous amount to pay, irrespective of how good a player is. At this point, the phrase ‘Holy overpay’ should be replaced by ‘Holy Walker.’

What’s worse is that Dallas drafted Hall of Famer Emmitt Smith, Darren Woodson, Russell Maryland, and Kevin Smith. Minnesota handed Dallas the materials to build a Super Bowl team and due to this trade, the Cowboys won three Lombardi Trophies in the coming years.

As for Herschel Walker’s time in Minnesota? He did alright, but the Vikings never made it past the Wild Card Round, so that should summarize how it went for them.

1. Browns trade for Deshaun Watson

The worst deal in NFL history was one made just three years ago. The Cleveland Browns traded for quarterback Deshaun Watson after his best season in the NFL and offered him an unprecedented amount of money. Cleveland sent six draft picks, three of whom were first-round picks, and offered the quarterback $230 million FULLY-GUARANTEED.

Deshaun Watson
Deshaun Watson (Image via IMAGO)

At the time, it would have seemed to be a great deal because Watson was frankly that good. However, the Browns traded for him at a time when his future was in jeopardy. The quarterback was fighting 24 cases of alleged sexual misconduct. The NFL was looking into him over the same but was yet to announce a penalty, and there comes Cleveland, Watson’s knight in shining armour, and offers him the world.

Deshaun Watson was suspended for 11 games. He then came back but has not played half-as-well as he did while in Houston. The quarterback has struggled with being available as a shoulder injury cut his season short in 2023 and this year; he got off to a horrendous start. He played five games this year and an unfortunate Achilles rupture ended his season short.

Recently, news emerged that the quarterback is likely to miss the 2025 season as well. Watson’s QBR was 23.1 through five weeks. He struggled to throw, he barely ran, and week-over-week, the Browns looked bad for making this deal.

The Texans, on the contrary, are thriving. The draft capital they got from this deal helped them build the elite team they have in place now. The likes of John Metchie III, Dameon Pierce, Will Anderson Jr., Tank Dell, Cade Stover, and others are directly or indirectly by-products of Watson’s trade.

Deshaun Watson has more cases against him than he does touchdowns with the Browns. Cleveland lost a lot and gained nothing from this trade, which is why it is the worst in NFL history.