NFL trades can build dynasties and powerhouse franchises. Before we take up worst NFL trades, Can you tell why NFL trades are important?
A great trade sets a team up for years of success and dominance, inspiring the future generation. But a bad one? It sinks franchises and can leave fans shaking their heads for decades.
History has seen many trades where teams gave up future Hall of Famers or placed their trust in the wrong player which sometimes make their franchises look foolish.
From giving up future Hall of Famers to betting the house on the wrong guy, history is full of trades that make teams (and their GMs) look foolish.
Some of these deals were disasters from the start while others horribly grew bad to worst NFL trades over the period of time.
Here we come up with some of the worst trades in the NFL history, why they happened and how they went so wrong.
What Makes a Trade a Total Disaster?
Not every bad trade looks awful right away at beginning. Some seem reasonable at the time but spiral into disaster due to:
- Lopsided talent exchange – One team gets a superstar while the other gets almost nothing.
- Lost draft picks – Giving up too many picks can cripple a franchise’s future.
- Terrible contracts – Paying big money for a player who flops is a nightmare for the team and franchises.
- Franchise setback – Some bad trades leave teams stuck in mediocrity for years.
What are the names popping up in your mind? These are the biggest trade blunders in NFL history.
The Herschel Walker Trade (1989) – The Deal That Built a Dynasty
This one is THE blueprint for how to ruin a franchise with one bad trade.
The Trade
Minnesota Vikings get: RB Herschel Walker, three late-round picks
Dallas Cowboys get: Five players and EIGHT draft picks.
Why It Was a Disaster for the Vikings
The Vikings thought they were getting a game-changing running back to push them to a Super Bowl. Instead, they got two and a half forgettable seasons from Walker, who never lived up to expectations.
Meanwhile, the Cowboys used the draft picks to build a dynasty, landing stars like Emmitt Smith, Darren Woodson, and Russell Maryland.
Dallas went on to win three Super Bowls in the 1990s, while Minnesota never even reached one.
Lesson Learned:
Never sell the future for a short-term fix—especially if the short-term fix isn’t even that great.
The Ricky Williams Trade (1999) – Betting It All on One Player
Mike Ditka must have really loved Ricky Williams because he traded away an entire draft class to get him.
The Trade
New Orleans Saints get: RB Ricky Williams
Washington gets: All of the Saints’ 1999 draft picks AND two more picks in 2000.
Why It Was a Disaster for the Saints
Williams was talented, but no running back is worth eight draft picks. Injuries and off-field issues kept him from ever becoming a true franchise player.
To make matters worse, the Saints’ lack of draft picks crippled their ability to build a team. Ditka was fired after the season, and Williams was gone a few years later.
Lesson Learned:
Never sacrifice depth for one player—football is a team sport for a reason.
The Brock Osweiler Trade (2017) – Paying to Get Worse
Sometimes, a bad trade isn’t about giving up a great player—it’s about taking on a terrible contract.
The Trade
Cleveland Browns get: QB Brock Osweiler AND a second-round pick
Houston Texans get: Cap space (they literally gave Osweiler away).
Why It Was a Disaster for the Browns
Osweiler had signed a four-year, $72 million contract with Houston but played so badly that the Texans just wanted to get rid of him.
The Browns took him only for the draft pick and then cut him before he even played a game.
Cleveland basically paid $16 million for nothing.
Lesson Learned:
Never buy a bad contract unless you actually have a plan for the player.
The Khalil Mack Trade (2018) – Giving Away a Superstar
Sometimes, giving up a star player is just as bad as trading for the wrong one.
The Trade
Chicago Bears get: LB Khalil Mack, a second-round pick
Oakland Raiders get: Two first-round picks and other assets.
Why It Was a Disaster for the Raiders
Mack was one of the best defensive players in the league, and the Bears immediately benefited from his presence.
The Raiders? They failed to turn their draft picks into anything special. Meanwhile, their defense—without Mack—became one of the worst in the NFL.
Lesson Learned:
If you already have a proven superstar, maybe just… keep him?
Honorable Mentions: Other NFL Trade Nightmares
- DeAndre Hopkins to Arizona (2020)
The Texans traded one of the best WRs in the NFL for… RB David Johnson and a second-round pick.
Hopkins thrived in Arizona, while the Texans got worse immediately. - Sam Bradford to the Vikings (2016)
The Vikings gave up a first-round pick for an injury-prone QB.
Bradford was gone after two seasons, and Minnesota didn’t win anything. - Antonio Brown to the Raiders (2019)
The Raiders traded for Brown… but he never played a single game due to off-field drama.
They lost draft capital and got absolutely nothing in return.
Why Do NFL Teams Keep Making Bad Trades?
Even with advanced scouting and analytics, teams still make awful trades. Why?
Desperation for a quick fix – Teams under often make reckless moves.
- Ignoring team fit – A great player in one system might flop in another.
- Overpaying for potential – Some teams bet too much on unproven players.
- PR pressure – Owners and GMs sometimes make splashy moves just to excite fans.
Could We See Another Blockbuster Bust Soon?
Bad trades aren’t going away anytime soon. In fact, some recent ones like the Russell Wilson trade to Denver are already starting to look ugly.
History shows that teams don’t always learn from past mistakes, which means we’ll probably see another massive trade failure soon.
Conclusion
NFL history is full of trades that went horribly wrong, leaving teams stuck in years of mediocrity. Whether it’s giving up too much for a single player or trading away a franchise cornerstone, these deals serve as cautionary tales for every front office.
What do you think was the worst trade in NFL history? Drop your thoughts in the now🏈.
