Ranking the Most Memorable Trades in NFL History
In the NFL, trades aren’t just front-office decisions; they can change the fate of franchises and rewrite history. Some teams strike gold, landing a future Hall of Famer who leads them to championships. Others? Well, let’s just say they end up on the wrong side of highlight reels.
From deals that built dynasties to trades that still have fans shaking their heads, these are the 15 most unforgettable swaps in NFL history. Buckle up—some of these are wild.
The Herschel Walker Trade (1989)
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The trade that built an empire, and just not for the team that made the deal. The Minnesota Vikings gave up a king’s ransom for running back Herschel Walker, hoping he would be the missing piece to a Super Bowl run. Instead, the Dallas Cowboys turned those draft picks into players like Emmitt Smith, Darren Woodson, and Russell Maryland, laying the foundation for three championships in the ‘90s.
The Ricky Williams Trade (1999)
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It’s not every day a team trades an entire draft class for one player, but that’s exactly what New Orleans Saints coach Mike Ditka did for Ricky Williams. The Saints gave up all of their 1999 draft picks, plus two picks in 2000, just to move up seven spots and take Williams at No. 5. The move backfired spectacularly, with Ditka getting fired a year later and Williams finding more success in Miami than New Orleans.
The Marshall Faulk Trade (1999)
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Sometimes, a trade works out for everyone. The Indianapolis Colts shipped star running back Marshall Faulk to the St. Louis Rams, making room for rookie Edgerrin James. Meanwhile, Faulk became the centerpiece of the “Greatest Show on Turf,” leading the Rams to a Super Bowl and guaranteeing his Hall of Fame legacy.
The Eli Manning–Philip Rivers Swap (2004)
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Eli Manning, selected first overall by the Chargers, refused to play for them. This forced a trade that sent him to the New York Giants while Philip Rivers headed to San Diego. Manning went on to win two Super Bowls, famously taking down the undefeated Patriots in 2007. Rivers had a fantastic career but never won a championship.
The Brett Favre Trade (1992)
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The Atlanta Falcons traded Brett Favre to the Green Bay Packers for a second-round pick, believing he wasn’t worth keeping around. That decision aged about as well as milk left in the sun. Favre went on to win three MVPs and a Super Bowl in Green Bay, proving himself as one of the greatest quarterbacks of all time.
The Joe Montana Trade (1993)
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Trading away a four-time Super Bowl champion is never easy, but the San Francisco 49ers were ready to move forward with Steve Young. Joe Montana was sent to the Kansas City Chiefs, where he proved he still had gas left in the tank, leading them to the AFC Championship Game. While the 49ers won another title with Young, Montana’s impact in Kansas City made this a deal worth remembering.
The Steve Young Trade (1987)
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Speaking of Steve Young, he wasn’t always a 49ers legend. He started his career with the struggling Tampa Bay Buccaneers before being dealt to San Francisco for a couple of mid-round picks. Under Bill Walsh’s system, Young developed into a Hall of Famer and led the 49ers to a Super Bowl. Meanwhile, Tampa Bay continued its tradition of bad quarterback decisions for another decade.
The Randy Moss Trade to New England (2007)
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The Oakland Raiders essentially gave away Randy Moss, sending him to the Patriots for a fourth-round pick. All he did in New England was set the NFL record for receiving touchdowns in a single season (23) while helping the Patriots go 16-0 in the regular season. The Raiders, well, they continued being the Raiders.
The Khalil Mack Trade (2018)
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The Raiders struck again, this time trading away All-Pro pass rusher Khalil Mack to the Chicago Bears. While Mack immediately altered the Bears’ defense, the Raiders used the draft picks they received to rebuild their roster. The long-term winner of this trade is still up for debate, but at the time, it shocked the NFL.
The Jay Cutler Trade (2009)
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The Denver Broncos were ready to move on from Jay Cutler and found a taker in the Chicago Bears. The Bears sent multiple picks and Kyle Orton to Denver, hoping Cutler was their long-term answer at quarterback. While Cutler had some good seasons in Chicago, he never quite lived up to the hype. The Broncos, meanwhile, used one of those picks to eventually land Demaryius Thomas, who became a key player in their Super Bowl-winning team.
The DeAndre Hopkins Trade (2020)
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This one still stings for Houston Texans fans. The team traded All-Pro wide receiver DeAndre Hopkins to the Arizona Cardinals for running back David Johnson and a second-round pick. Hopkins continued dominating in Arizona while the Texans quickly spiraled into chaos.
The Eric Dickerson Trade (1987)
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One of the biggest trades in NFL history involved Eric Dickerson’s move from the Los Angeles Rams to the Indianapolis Colts in a massive three-team deal. The Rams received a haul of draft picks, while the Colts received one of the best running backs in the league. Dickerson remained productive in Indianapolis, but this trade ultimately reshaped multiple franchises.
The Carson Palmer Trade (2011)
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After a bitter falling-out with the Cincinnati Bengals, Carson Palmer was sent to the Raiders for multiple draft picks. Unfortunately for Oakland, Palmer never lived up to expectations, and the Bengals used the picks to rebuild their roster. The deal was yet another example of the Raiders’ struggles with major trades.
The Amari Cooper Trade (2018)
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Midway through the 2018 season, the Dallas Cowboys traded a first-round pick for Amari Cooper. Many thought the price was too steep, but Cooper immediately turned things around for Dallas, helping them make the playoffs. The Raiders used that first-round pick on a promising player, but Cooper’s impact in Dallas made this a win-now move that actually paid off.
The Matthew Stafford–Jared Goff Swap (2021)
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One of the rare quarterback-for-quarterback trades, this deal sent Matthew Stafford to the Rams and Jared Goff to the Lions. Stafford delivered immediately, leading the Rams to a Super Bowl win. Goff, however, has found a new home in Detroit, guiding the Lions to unexpected success. This trade worked out for both sides, but the instant championship edge went to the Rams.