a Yourlist ranking · the crowd decides the order
Vote on which trade turned out to be the biggest disaster for the team that made it — the deals that haunted front offices and fan bases for decades afterward.
What counts: Ranked by how lopsided and consequential the trade proved to be for the losing side — Hall of Fame production given away, championships enabled for the other team, careers derailed. All years, prices, and ratings are approximate and reflect historical consensus, not verified exact figures.
Babe Ruth Sold to the Yankees
In 1919, cash-strapped Red Sox owner Harry Frazee sold Babe Ruth to the Yankees for $125,000, reportedly to help finance a Broadway show, launching the 'Curse of the Bambino' as Boston went 86 years without a title while New York built the sport's greatest dynasty around Ruth's b
Year: 1919Sport: BaseballTeam Fleeced: Boston Red SoxInfamy Rating: 10/10
added by IJRin 2 rankings
Ricky Williams Draft-Day Trade
Saints coach Mike Ditka was so smitten with Ricky Williams that in 1999 he traded nearly the Saints' entire draft, eight picks including two future first-rounders, just to move up and grab him. Williams never came close to justifying the cost, and the deal became shorthand for dr
Year: 1999Sport: FootballTeam Fleeced: New Orleans SaintsInfamy Rating: 9/10
added by IJR
Herschel Walker Mega-Trade
The Vikings sent a mountain of players and draft picks to Dallas for Herschel Walker in 1989, and the Cowboys used that haul to build the roster that won three Super Bowls in the 1990s. Walker was a solid running back, but he wasn't three-championships solid, making this the blue
Year: 1989Sport: FootballTeam Fleeced: Minnesota VikingsInfamy Rating: 9/10
added by IJR
McHale/Parish Draft-Night Trade
On draft night 1980, Golden State sent the rights to the No. 1 pick, used on Joe Barry Carroll, plus more, to Boston for the rights to Robert Parish and the pick that became Kevin McHale. Both became Hall of Famers and pillars of three Celtics titles while Carroll fizzled out, ma
Year: 1980Sport: BasketballTeam Fleeced: Golden State WarriorsInfamy Rating: 9/10
added by IJR
Wayne Gretzky to the Kings
The Great One's stunning 1988 trade from Edmonton to Los Angeles shocked Canada and helped globalize hockey, but Edmonton gave up the greatest player the sport has ever seen for cash and prospects. Oilers fans still treat it as a national wound, even though the team won one more
Year: 1988Sport: HockeyTeam Fleeced: Edmonton OilersInfamy Rating: 8/10
added by IJR
Nolan Ryan for Jim Fregosi
Tired of Nolan Ryan's control issues, the Mets dealt him to the Angels in 1971 for aging shortstop Jim Fregosi, who flopped in New York. Ryan went on to throw seven no-hitters and strike out over 5,000 batters, turning this into the gold standard of baseball's worst-trade convers
Year: 1971Sport: BaseballTeam Fleeced: New York MetsInfamy Rating: 8/10
added by IJRin 2 rankings
John Smoltz for Doyle Alexander
In 1987, Detroit rented 34-year-old Doyle Alexander from Atlanta for a playoff push, giving up a 20-year-old minor leaguer named John Smoltz. Alexander helped the Tigers win their division that year; Smoltz became a Hall of Fame ace and the backbone of Atlanta's 1990s dynasty for
Year: 1987Sport: BaseballTeam Fleeced: Detroit TigersInfamy Rating: 8/10
added by IJR
Jeff Bagwell for Larry Andersen
Chasing a playoff spot in 1990, Boston traded prospect Jeff Bagwell to Houston for 37-year-old reliever Larry Andersen, who pitched about 15 innings for the Sox down the stretch. Bagwell went on to hit 449 home runs and win an MVP award for the Astros, a swap Red Sox fans still w
Year: 1990Sport: BaseballTeam Fleeced: Boston Red SoxInfamy Rating: 7/10
added by IJRin 2 rankings
Sammy Sosa for George Bell
The White Sox shipped a young, raw Sammy Sosa across town to the Cubs in 1992 for aging slugger George Bell, who lasted one mediocre season on the South Side. Sosa erupted into a 600-plus-home-run superstar for Chicago's North Siders, making this an intra-city embarrassment that
Year: 1992Sport: BaseballTeam Fleeced: Chicago White SoxInfamy Rating: 7/10
added by IJR
McGriff/Fernandez for Alomar/Carter
San Diego dealt Fred McGriff and Tony Fernandez to Toronto in 1990 for Roberto Alomar and Joe Carter in a swap that looked even at the time. Alomar became a Hall of Famer and Carter hit a World Series-winning walk-off homer for the Blue Jays, tipping this decisively in Toronto's
Year: 1990Sport: BaseballTeam Fleeced: San Diego PadresInfamy Rating: 7/10
added by IJR
James Harden Trade
Worried about the luxury tax, Oklahoma City traded reigning Sixth Man of the Year James Harden to Houston in 2012 rather than pay him a max extension. Harden became a scoring machine and MVP for the Rockets while the Thunder's championship window with Durant and Westbrook quietly
Year: 2012Sport: BasketballTeam Fleeced: Oklahoma City ThunderInfamy Rating: 6/10
added by IJR
Chris Webber for Tom Gugliotta
After a coaching feud, Golden State shipped rookie sensation Chris Webber to Washington in 1994 for Tom Gugliotta and three first-round picks. Webber blossomed into a five-time All-Star and franchise icon for the Sacramento Kings, while the Warriors spent the next decade largely
Year: 1994Sport: BasketballTeam Fleeced: Golden State WarriorsInfamy Rating: 6/10
added by IJR
Kareem Abdul-Jabbar to the Lakers
Unable to keep its unhappy superstar center in the Midwest, Milwaukee traded Kareem Abdul-Jabbar to the Lakers in 1975. Kareem went on to win five more championships and become the NBA's all-time leading scorer, while the Bucks entered a long rebuilding era that never fully recov
Year: 1975Sport: BasketballTeam Fleeced: Milwaukee BucksInfamy Rating: 6/10
added by IJRin 2 rankings
Brett Favre to Green Bay
Atlanta gave up on a wild, unproven backup named Brett Favre after one rocky season, trading him to Green Bay in 1992 for a first-round pick. Favre became a three-time MVP and Super Bowl champion for the Packers, cementing this as one of the NFL's great what-might-have-beens for
Year: 1992Sport: FootballTeam Fleeced: Atlanta FalconsInfamy Rating: 5/10
added by IJR
Jay Cutler to the Bears
Denver traded franchise quarterback Jay Cutler to Chicago in 2009 amid a personality clash with new coach Josh McDaniels, netting Kyle Orton and draft picks in return. Cutler gave Chicago a decade of erratic but talented quarterback play while Denver's post-Cutler carousel spun f
Year: 2009Sport: FootballTeam Fleeced: Denver BroncosInfamy Rating: 5/10
added by IJR
Khalil Mack to the Bears
Oakland traded All-Pro pass rusher Khalil Mack to Chicago right before the 2018 season after a contract standoff, netting two first-round picks. Mack anchored a dominant Bears defense for years while the Raiders' rebuild dragged on, another star holdout that ended up favoring the
Year: 2018Sport: FootballTeam Fleeced: Oakland RaidersInfamy Rating: 5/10
added by IJR
Quebec flipped the draft rights to holdout phenom Eric Lindros to Philadelphia in 1992 for a package of players, picks, and cash, then used that return to help build the core, Sakic, Forsberg, Roy, that won two Stanley Cups after relocating to Colorado. Lindros became a superstar
Year: 1992Sport: HockeyTeam Fleeced: Quebec NordiquesInfamy Rating: 4/10
added by IJREric Lindros trade
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