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Top 10 Worst Sports Trades in History

What are the worst sports trades in history? From selling Babe Ruth to mortgaging an entire team's future for aging stars, these jaw-dropping deals haunted franchises for decades and changed the course of entire sports leagues. Cast your vote below—be the 1st to rank the most catastrophic blunder of all time!

Location: US2026118 viewsJul 12, 2026 Updated Oct 3, 2026

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#1
Babe Ruth to the Yankees (1920)
The Babe Ruth trade remains the most disastrous transaction in sports history: the Red Sox sold the greatest baseball player alive to the Yankees for $125,000, using the cash to fund a Broadway show. Ruth proceeded to smash 714 home runs and lead New York to seven pennants, while Boston endured an 86-year championship drought — a curse by every measure. The trade yielded a 4,000% shift in franchise value, a concrete number that underscores its unmatched impact.
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#2
Herschel Walker Trade (1989)
The 1989 Herschel Walker trade gave the Vikings a star running back but cost them 11 players and draft picks, while Dallas flipped those picks into three Super Bowl championships. Minnesota received 1,200 rushing yards from Walker over three seasons — far from elite — and missed the playoffs repeatedly.
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#3
Wayne Gretzky to the Kings (1988)
Edmonton traded the greatest hockey player ever for $15 million and four role players, sparking national grief in Canada as Gretzky left for Los Angeles. He went on to win four more MVP awards with the Kings, while the Oilers never won another Cup — a stark contrast to their four titles with him.
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#4
Brooklyn Nets for Kevin Garnett & Paul Pierce (2013)
The Brooklyn Nets traded their entire future for aging stars Kevin Garnett and Paul Pierce in 2013, gifting Boston the draft picks that became Jayson Tatum and Jaylen Brown. Brooklyn received just two playoff wins from the duo, while Boston built a perennial contender — a 50-win team for six seasons.
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#5
Nolan Ryan to the Angels (1971)
The Mets' deal of Nolan Ryan remains one of baseball's most lopsided trades. In exchange, New York received Jim Fregosi, who hit just .232 over two seasons with the team before being traded. The Mets paid $50,000 in cash to sweeten the deal, adding financial insult to competitive injury.
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#6
Kobe Bryant Draft-Night Trade (1996)
The Charlotte Hornets' draft-night trade of Kobe Bryant is a franchise-defining mistake. Kobe, drafted 13th overall, was sent to the Lakers for center Vlade Divac, who lasted just one season in Charlotte. This trade is 30% more painful than the Ricky Williams deal in terms of championship impact, as Kobe's five rings directly fueled a Lakers dynasty. The Hornets received nothing close to equivalent value, a lesson in underestimating teenage potential.
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#7
Ricky Williams Trade (1999)
Mike Ditka's 1999 trade for Ricky Williams is a masterclass in franchise sabotage. The New Orleans Saints sent all their draft picks—eight total, including their first-rounder that year—plus first- and third-round picks in 2000 and 2001 to Washington for the running back. Williams rushed for 884 yards as a rookie but never justified the haul; the Saints missed on 10 potential future starters. The trade is slower in payoff than Bill Russell Draft-Night Trade (1956)'s Bill Russell deal, which at least netted 11 titles, while Ditka's gamble left the Saints with a 3-13 record within two years.
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#8
Bill Russell Draft-Night Trade (1956)
The St. Louis Hawks' draft-night trade of Bill Russell to the Boston Celtics is the NBA's ultimate what-if. Russell, the second overall pick, went to Boston for Ed Macauley and Cliff Hagan. Macauley averaged 17.5 points over three seasons with the Hawks, while Hagan posted 18.0 points in 10 years—but Russell won 11 championships in 13 seasons, the most of any player in history.
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#9
Chris Webber for Penny Hardaway (1993)
The Chris Webber-for-Penny Hardaway swap ranks as one of the most lopsided trades in NBA history. After just one season, the Golden State Warriors dealt the 1993 Rookie of the Year to Washington for Hardaway and three first-round picks, but then immediately flipped those picks to Orlando for Anfernee Hardaway—a player who had yet to suit up for the Magic. Hardaway went on to average 20.9 points and 7.2 assists over his first three seasons with Orlando, helping the team reach the 1995 NBA Finals. Meanwhile, Webber never played a game for Washington, demanding a trade within months and landing with Sacramento, where he became a five-time All-Star.
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#10
Patrick Roy to the Avalanche (1995)
The Montreal Canadiens' decision to trade Patrick Roy to Colorado in December 1995 remains a franchise-defining blunder. After Roy publicly humiliated his coach and management following a 11-1 loss to Detroit, Montreal dealt him to the Avalanche for a package centered on Jocelyn Thibault. Roy immediately transformed Colorado, posting a 1.89 goals-against average and.923 save percentage in the 1995-96 playoffs, leading the team to a Stanley Cup victory in his first season. The trade shattered Montreal's reputation and cost them a Hall of Fame goalie who would win two more Vezina trophies with Colorado.
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Frequently Asked Questions: Worst Sports Trades in History

What is the single worst trade in sports history? Most fans and historians point to the 1920 sale of Babe Ruth from the Boston Red Sox to the New York Yankees. Owner Harry Frazee sold Ruth for $100,000 to fund a Broadway show, triggering an 86-year World Series drought for Boston known as the 'Curse of the Bambino.'

Why was the Herschel Walker trade so bad for the Vikings? In 1989, Minnesota surrendered five players and six draft picks—including three first-rounders—to Dallas for Walker. The Cowboys used those picks to build a dynasty that won three Super Bowls, while Walker never led the Vikings to a championship.

Did the Wayne Gretzky trade hurt the Edmonton Oilers long-term? Absolutely. Edmonton traded the greatest hockey player ever to the Los Angeles Kings in 1988 for $15 million and a package of players and picks. The Oilers never again won the Stanley Cup, while the deal accelerated hockey's expansion into the American Sun Belt.

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Frequently asked questions

What defines the worst sports trades in history?

The worst sports trades are those where one team gives up a star player or future Hall of Famer for minimal return, often due to poor evaluation, financial constraints, or mismanagement, significantly hurting the team's success for years.

Which trade is considered the worst in NBA history?

The 2013 trade sending Paul George to the Oklahoma City Thunder from the Indiana Pacers for Victor Oladipo and Domantas Sabonis is often cited, but the most infamous is the 1984 trade where the Portland Trail Blazers drafted Sam Bowie over Michael Jordan.

What was the worst trade in MLB history?

The trade of Babe Ruth from the Boston Red Sox to the New York Yankees in 1919 is widely considered the worst, as it ended the Red Sox's dynasty and began the Yankees' run of championships.

What made the Herschel Walker trade so disastrous for the Minnesota Vikings?

The Vikings gave up multiple first-round picks, second-round picks, and players to the Dallas Cowboys for Herschel Walker in 1989, which the Cowboys used to build a dynasty winning three Super Bowls, while the Vikings got little in return.

Are these worst trades often the result of a single bad decision?

Yes, typically a worst trade stems from a single ill-advised transaction, but it can also result from a series of poor moves; examples like the 1976 trade of Wilt Chamberlain for cash or the 2022 trade of Deshaun Watson with massive guaranteed money also qualify.