The 2024 NFL trade deadline is set to roll around on November 5th, and plenty of teams have already made some notable moves in the hopes of improving their position as they head into the second half of the season.

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There’s only so much NFL teams can do to ensure they end up on the right side of a trade when everything is said and done, and there are obviously plenty of franchises that have had a transaction come back to bite them in a big way.
However, it’s hard to top the ones that firmly earned their spot on the list of the biggest regrets.
Herschel Walker To The Vikings

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It’s easy to understand why the Vikings decided to trade for Herschel Walker midway through the season in 1989, as the running back was a two-time Pro Bowler with the Cowboys who appeared to have a bright future ahead of him.
However, Walker only spent two-and-a-half seasons in Minnesota and failed to come close to performing like he had in Dallas. The Cowboys, on the other hand, ended up getting a slew of draft picks that were ultimately used to scoop up a bunch of guys—most notably Emmitt Smith—who played key roles in helping the team secure three Super Bowls in the 1990s.
Deshaun Watson To The Browns

There’s a very slim chance Deshaun Watson is able to turn things around with the Browns, but it’s very hard to believe that’s going to be the case thanks to what’s transpired since he arrived in Cleveland.
The Texans received six draft picks after sending Watson to the Browns in 2022, and Cleveland’s decision to immediately give him a fully guaranteed $230 million contract has the potential to be one of the most boneheaded moves in the history of the league.
Houston, on the other hand, used some of those picks to secure the talents of C. J. Stroud and Will Anderson Jr., and they’ve firmly emerged as the winner of the trade.
Brett Favre To The Packers

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The Falcons drafted Brett Favre with the 33rd overall pick in the 1991 NFL Draft much to the chagrin of head coach Jerry Glanville, and he only played four snaps during a rookie season where Chris Miller served as the primary starter.
In 1992, Favre was shipped off to the Packers in exchange for a first-round pick that the Falcons eventually used to draft Tony Smith.
Smith only spent three seasons in the NFL, while Favre ended up playing in Green Bay for 16 years while racking up three MVPs and a Super Bowl.
Jerome Bettis To The Steelers

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Jerome Bettis spent his first three seasons with the Rams, but the team opted to go in a new direction at running back by targeting Lawrence Phillips in the 1996 NFL Draft.
Phillips was a notorious bust whose career was derailed by off-the-field issues that had already raised plenty of flags during his time at Nebraska.
“The Bus,” on the other hand, thrived after getting a change of scenery, as he spent the last 10 seasons of his career in Pittsburgh, recorded at least 1,000 yards in his first six, and capped off his tenure with a Super Bowl en route to being enshrined in the Hall of Fame.
Russell Wilson To The Broncos

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As was the case with Bettis, it appears Russell Wilson is settling in pretty well in Pittsburgh, but the same can’t be said about what unfolded after he ended up in Denver.
In 2022, Russell Wilson was sent to the Broncos in a blockbuster trade where the Seahawks received Drew Lock, Noah Fant, Shelby Harris, and five draft picks.
It’s a bit too early to come to any sweeping conclusions about Seattle’s eventual haul, but Wilson was an unmitigated disaster for the Broncos over the course of two seasons where he posted an 11-19 record as a starter.
Ricky Williams To The Saints

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In 1999, Mike Ditka decided to do everything in his power to acquire Ricky Williams, and he eventually got his wish after New Orleans moved up to the fifth spot in the draft by sending eight picks (including every other one it held that year) to Washington.
The team now known as the Commanders wasn’t necessarily able to capitalize in a big way, but they did end up acquiring notable names including LaVar Arrington and Champ Bailey.
Williams, on the other hand, only spent three seasons with the Saints, and 1999 marked Ditka’s final year as an NFL coach after the team went 3-13.
DeAndre Hopkins To The Cardinals

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It was pretty clear the Cardinals fleeced the Texans when they traded for DeAndre Hopkins and a fourth-round pick in exchange for David Johnson and a couple of selections in 2020—and that ended up being the case.
The running back only averaged 36.8 yards a game during the two seasons he spent in Houston, while Hopkins quickly emerged as the top receiver for the Cardinals while averaging 77 receiving yards and hauling in 17 touchdowns in the 35 games he ended up playing in Arizona.
Jeff George To The Falcons

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The Colts traded up with the Falcons to select Jeff George out of Illinois with the first overall pick in the 1990 NFL Draft, but the QB ended up in Atlanta after going 14-35 in his first four seasons as a starter.
Indianapolis received two first-round picks and committed an idiotic trade of its own by sending one to a 49ers team that used it to select future Hall of Famer Bryant Young. However, the Colts used the second to acquire Marvin Harrison, which ended up working out pretty well for them.
George, on the other hand, went 16-19 during his time in Atlanta. He did help lead them to the playoffs in 1995, but the following year, he was suspended for the rest of the season after getting into an argument with Falcons coach June Jones on the sidelines just three games into the campaign and subsequently signed with the Raiders.
John Hadl To The Packers

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This is fairly ancient history compared to the rest of the trades on this list, but it’s still worth mentioning.
The Packers were in fairly desperate need of a QB midway through the 1974 season, and they thought 34-year-old John Hadl had what it took to help them turn things around and make the playoffs after getting off to a 3-3 start.
The Rams received three draft picks in exchange for Hadl (who Green Bay targeted after a trade for Archie Manning fell through), but the QB imploded after joining the Packers while posting a 7-12 record as a starter during a tenure where he threw nine touchdowns and 29 interceptions.