In the high-stakes world of professional sports, trades can make or break a franchise. While some swaps elevate teams to glory, others become legendary for all the wrong reasons. From short-sighted decisions to gross miscalculations, here are the top 10 worst sports trades of all time, reminding us that hindsight is always 20/20.
1. Babe Ruth to the Yankees (1919)
Trade Details:
Boston Red Sox: Sold Babe Ruth for $100,000.
New York Yankees: Received Babe Ruth.
This trade, often referred to as the "Curse of the Bambino," stands as the quintessential cautionary tale in sports history. The Red Sox offloaded Ruth to finance a Broadway play, while Ruth went on to transform the Yankees into a dynasty. The Sox endured an 86-year championship drought, while Ruth cemented his legacy as one of the greatest athletes ever.
2. Wayne Gretzky to the Kings (1988)
Trade Details:
Edmonton Oilers: Received Jimmy Carson, Martin Gelinas, first-round picks in 1989, 1991, and 1993, plus $15 million.
Los Angeles Kings: Received Wayne Gretzky, Mike Krushelnyski, and Marty McSorley.
Trading "The Great One" shocked the hockey world. While the Oilers initially managed to stay competitive, Gretzky's departure ended their dynasty. Meanwhile, he brought hockey to the forefront in the U.S., turning the Kings into a legitimate franchise. Edmonton fans still lament losing the greatest hockey player ever.
3. Herschel Walker to the Vikings (1989)
Trade Details:
Dallas Cowboys: Received five players (LB Jesse Solomon, CB Issiac Holt, RB Darrin Nelson, LB David Howard, DE Alex Stewart) and six draft picks, including three first-rounders (used to draft RB Emmitt Smith, DT Russell Maryland, and S Darren Woodson).
Minnesota Vikings: Received Herschel Walker and four mid-round draft picks.
This trade backfired spectacularly for the Vikings, who failed to capitalize on Walker's talent. The Cowboys, however, used the draft picks to build a dynasty in the 1990s. Dallas won three Super Bowls, while Minnesota gained nothing of note.
4. Boston Celtics Trade Bill Russell (1956)
Trade Details:
St. Louis Hawks: Received Ed Macauley and Cliff Hagan.
Boston Celtics: Received the draft rights to Bill Russell.
Russell became a cornerstone for Boston, leading them to 11 NBA championships in 13 seasons. St. Louis, on the other hand, watched in agony as Russell dominated the league, setting records that still stand today.
5. Nolan Ryan to the Angels (1971)
Trade Details:
New York Mets: Received Jim Fregosi.
California Angels: Received Nolan Ryan, Don Rose, Leroy Stanton, and Francisco Estrada.
The Mets traded away a young pitcher with blazing speed for an aging shortstop. Ryan went on to have a legendary career, throwing seven no-hitters and racking up 5,714 strikeouts. Fregosi fizzled out, and the Mets were left wondering what could have been.
6. Kawhi Leonard to the Spurs (2011)
Trade Details:
Indiana Pacers: Received George Hill.
San Antonio Spurs: Received Kawhi Leonard, Davis Bertans, and Erazem Lorbek.
At the time, Hill seemed like a solid pickup for Indiana, but Leonard evolved into one of the NBA's top players. He won Finals MVP twice and led the Spurs and later the Raptors to championships. Indiana, meanwhile, gained little traction in the playoffs.
7. Pedro Martínez to the Red Sox (1997)
Trade Details:
Montreal Expos: Received Carl Pavano and Tony Armas Jr.
Boston Red Sox: Received Pedro Martínez.
The Expos let go of Pedro Martínez, one of baseball's most dominant pitchers, for relatively unremarkable returns. Martínez went on to win two Cy Young Awards with Boston and helped break the "Curse of the Bambino" in 2004, leading the Sox to a World Series title.
8. Brett Favre to the Packers (1992)
Trade Details:
Atlanta Falcons: Received a first-round pick.
Green Bay Packers: Received Brett Favre.
The Falcons gave up on a young quarterback after just one season, trading him to Green Bay. Favre went on to become one of the NFL’s greatest quarterbacks, winning three MVP awards and a Super Bowl. The Falcons struggled with quarterback issues for years afterward.
9. James Harden to the Rockets (2012)
Trade Details:
Oklahoma City Thunder: Received Kevin Martin, Jeremy Lamb, two first-round draft picks (Steven Adams and Mitch McGary), and a second-round pick (Álex Abrines).
Houston Rockets: Received James Harden, Cole Aldrich, Daequan Cook, and Lazar Hayward.
This trade haunted the Thunder, who broke up a promising trio of Harden, Kevin Durant, and Russell Westbrook to save money. Harden became a perennial MVP contender in Houston, while Oklahoma City failed to win a title with the remaining pieces.
10. Caleb Williams Trade (2024)
Trade Details:
Chicago Bears: Received WR DJ Moore, a 2023 first-round pick (#9 overall), a 2023 second-round pick, and the Panthers’ 2024 first- and second-round picks.
Carolina Panthers: Received the #1 overall pick (used on QB Bryce Young).
This trade’s full legacy is yet to be determined, but it’s shaping up to be a lopsided deal in favor of the Bears. By trading away their future picks and a star receiver to draft Bryce Young, the Panthers have struggled in his rookie season. Meanwhile, the Bears are positioned to potentially draft Caleb Williams—a generational quarterback talent—with the Panthers’ 2024 first-round pick. If Williams lives up to the hype, this deal could go down as a franchise-altering mistake for Carolina.
Conclusion
Bad trades have ripple effects that last for decades, altering the trajectory of franchises and changing sports history. While fans can only hope their teams learn from these infamous examples, the reality is that the next disastrous trade may be just around the corner. After all, even the most seasoned executives can’t predict the future.