Christian McCaffrey (Photo By Nathan Ray Seebeck/Imagn Images) and Khalil Mack (Photo By Kirby Lee/Imagn Images)
The gap between the best and worst trades in NFL history often depends on perspective. However, some deals have been so surprising that they have shocked both fans and analysts.
In recent years, NFL general managers have become bolder, showing a greater willingness to trade up in the draft to secure top prospects or take big risks on veteran players they believe can elevate their teams. As a result, more unexpected and game-changing trades have taken place.
NFL’s Most Shocking Trades In History
5. Herschel Walker – Dallas Cowboys To Minnesota Vikings
Herschel Walker (Photo by Alex Wong/Getty Images)
By 1989, the Dallas Cowboys were among the worst teams in NFL history. New head coach Jimmy Johnson needed a rebuild, so he traded star running back Herschel Walker.
Walker, a former USFL standout, had multiple 1,000-yard seasons, making him a major asset. On October 12, Dallas sent him to the Vikings in an 18-player, three-team deal. Minnesota, chasing a Super Bowl, gave Dallas five players and multiple draft picks. Though Walker resisted leaving, the Cowboys paid him $1.25 million to agree.
Dallas used the picks to build a dynasty, while Minnesota collapsed. This trade reshaped how teams valued draft picks and rebuilt rosters.
4. Khalil Mack – Oakland Raiders To Chicago Bears
Khalil Mack (Photo by Will Newton/Getty Images)
The Raiders and Khalil Mack had a rough summer in 2018. Mack, the team’s star defender and 2016 Defensive Player of the Year, was unhappy with his contract and considered sitting out. Jon Gruden, the new head coach, had praised Mack when he took the job, but their relationship, along with his ties to owner Mark Davis, fell apart.
The Bears saw an opportunity and traded four draft picks for Mack, while the Raiders included two picks in return.
Mack dominated in his first season with Chicago, leading the Bears to an NFC North title, the league’s best defense, and an All-Pro selection. Meanwhile, the Raiders struggled and failed to capitalize on their extra draft picks.
3. Jimmy Garoppolo – New England Patriots To San Francisco 49ers
Jimmy Garoppolo (Photo by Ezra Shaw/Getty Images)
Bill Belichick saw Jimmy Garoppolo as the future of the Patriots. Drafted from Eastern Illinois, he wasn’t just Tom Brady’s backup—he proved his worth when filling in during Brady’s Deflategate suspension.
Garoppolo’s strong play caught Belichick’s attention and unsettled Brady. By 2016 and early 2017, tensions in New England were rising. Brady, feeling threatened, asked owner Robert Kraft to step in. Kraft sided with Brady, forcing Belichick to trade Garoppolo to the 49ers for a second-round pick.
Garoppolo thrived in San Francisco, winning his first five starts and later leading the team to Super Bowl 54. Meanwhile, the Patriots stuck with Brady, winning another title, but his 2020 departure left Belichick without a clear successor.
The trade revitalized the 49ers but left the Patriots struggling to replace Brady—a problem they still face today.
2. Von Miller – Denver Broncos To LA Rams
Von Miller (Photo by Timothy T Ludwig/Getty Images)
Miller was a Denver Broncos icon known for his unforgettable playoff performances, which led the team to victory in Super Bowl 50. He had planned to finish his career in Denver, but that changed in November 2021.
The Broncos traded Miller to the Rams in exchange for two 2022 draft picks. Though he didn’t want to leave, he had no choice but to say an emotional goodbye to Denver before heading to LA.
With the Rams, Miller became a game-changer, boosting their season and helping them secure a Super Bowl win. He was one of the final pieces in LA’s star-studded roster.
1. Christian McCaffrey – Carolina Panthers To San Francisco 49ers
Christian McCaffrey (Photo By Nathan Ray Seebeck/Imagn Images)
McCaffrey seemed destined to spend his entire career with the Carolina Panthers. Drafted in 2017 and given a huge contract in 2020, he appeared set to become a franchise legend. But injuries and the team’s struggles changed everything.
When Carolina fired head coach Matt Rhule in 2022, the 49ers seized the opportunity, trading four draft picks and taking on McCaffrey’s $64 million contract. Given his injury history, it looked like a risky move.
Now, it appears to be one of the best trades in recent history. McCaffrey has played at an MVP level, scoring in 15 straight regular-season games. The 49ers are the NFL’s top team, thanks to one of the league’s best offensive players.
