There’s nothing quite like the thrill of a blockbuster trade—until it goes completely off the rails. Some deals look questionable from the start, while others take years to fully reveal their awfulness.
But the worst ones? Those are the trades that haunt franchises, spark endless “what if” debates, and leave fans screaming into the void. Let’s take a look at the absolute worst trades in sports history—the ones that aged like expired milk.
10. The Boston Red Sox Sell Babe Ruth to the Yankees (1919)
What did Boston get? $100,000 and a loan to finance a Broadway play. What did New York get? Oh, just the most legendary player in baseball history. Babe Ruth went on to smash 714 home runs and lead the Yankees to four World Series titles, while the Red Sox endured an 86-year championship drought. Tough look.
9. The Charlotte Hornets Trade Kobe Bryant for Vlade Divac (1996)
Drafted 13th overall by Charlotte, an 18-year-old Kobe Bryant never played a single second for the Hornets. Instead, they shipped him to the Lakers for Vlade Divac, a solid but unspectacular center. Meanwhile, Kobe became a five-time NBA champion, a league MVP, and a basketball icon. Hornets fans, don’t look this one up. It hurts.
8. The Dallas Cowboys Trade Herschel Walker (1989)
The Cowboys sent Walker to the Minnesota Vikings for a boatload of draft picks. The Vikings thought they were getting a franchise-altering running back; instead, they just helped Dallas build a Super Bowl-winning roster. The Cowboys turned those picks into Emmitt Smith, Darren Woodson, and others who led them to three championships. The Vikings? They got two years of decent production from Walker and no rings to show for it. Ouch.
7. The Brooklyn Nets Trade Their Future for Aging Celtics Stars (2013)
The Nets wanted to fast-track their way to a championship, so they sent three first-round picks (and a pick swap) to Boston for Kevin Garnett, Paul Pierce, and Jason Terry—all in their late 30s. Boston used those picks to draft Jaylen Brown and Jayson Tatum, who became the foundation of a championship-caliber team. Brooklyn, meanwhile, crashed and burned within two seasons.
6. The Edmonton Oilers Trade Wayne Gretzky to the Kings (1988)
The Oilers, fresh off a Stanley Cup win, decided to trade Wayne Freaking Gretzky for a mix of players, draft picks, and—get this—cash considerations. Gretzky immediately made the Kings relevant, while Edmonton faded from dominance. Trading the greatest hockey player of all time? Questionable decision, to say the least.
5. The Mariners Give Up David Ortiz for Absolutely Nothing (1996)
Seattle signed Ortiz as a teenager but then gave him away for free to the Twins. The kicker? Minnesota also cut him a few years later. Ortiz, of course, landed in Boston, won three World Series titles, and became one of the most clutch hitters in MLB history. Mariners fans can only wonder what might have been.
4. The Cleveland Browns Trade the No. 12 Pick (Deshaun Watson) to Houston (2017)
The Browns owned the No. 12 pick in the 2017 draft but decided to trade it to Houston. The Texans used it to draft Deshaun Watson, while Cleveland continued its endless search for a quarterback. And just to make things worse? A few years later, the Browns traded the farm to Houston to get Watson back, this time giving up three first-round picks and handing him a fully guaranteed contract. A double L.
3. The Red Wings Trade Marcel Dionne for Basically Nothing (1975)
The Red Wings decided that a 23-year-old Marcel Dionne wasn’t worth keeping, so they dealt him to the Kings in a package that included… Terry Harper and Dan Maloney (yes, really). Dionne went on to rack up 1,771 career points and became one of the greatest scorers in NHL history. Meanwhile, Detroit spent years in irrelevance before Steve Yzerman arrived in the ’80s.
Read More: The 15 Most Shocking NFL Trades That Completely Backfired
2. The Boston Bruins Trade Joe Thornton for a Bag of Pucks (2005)
Boston sent Thornton, their franchise center, to San Jose for Marco Sturm, Wayne Primeau, and Brad Stuart—none of whom moved the needle. Thornton? He won the MVP that season and became one of the best playmakers in hockey history. Bruins fans deserved better.
Read More: 20 Blockbuster NBA Trades That Left Fans Stunned
1. The Atlanta Hawks Trade Luka Dončić for Trae Young (2018)
On draft night 2018, the Hawks selected Luka Dončić but immediately sent him to Dallas in exchange for Trae Young and a future first-round pick. While Young is an All-Star talent, Luka has quickly become a generational superstar, drawing comparisons to LeBron and Magic with his all-around game. And now that the Mavs have traded Luka to LA, there’s a solid chance he could be involved in two of the most baffling NBA trades of all time.
Read More: The 18 Most Questionable Trades in Sports History
