Worst Trades in Sports History

April 29, 2019 by Grant Suneson

Professional sports teams use trades to improve their roster and prepare for the future — whether by trading a few key players to push an above-average squad to become a championship contender, or by loading up on draft picks to set the franchise up for future success.

Ideally, both teams involved in the trade have done enough research and planning that each side is improved by the swap. But this is not always the case. Throughout sports history, there have been dozens of notable cases in which teams traded away a future star and received almost no value in return.

Perhaps the most famous trade in sports history occurred a century ago, when the Boston Red Sox sold Babe Ruth to their rivals, the New York Yankees, for $100,000. Ruth proved to be worth much more than that, becoming one of the greatest players of all time with the Yankees. After the trade, the Red Sox failed to win a World Series for 86 years in what was known as The Curse of the Bambino.

Since that time, player scouting has improved and athletes have more control over their careers with the advent of free agency, so lopsided trades have become more rare. Still, from time to time, franchises completely miss the mark, dealing away a future star or giving up draft picks to acquire an unproductive player.

24/7 Wall St. reviewed famous trades in American sports history, using the Sports Reference family of sites, to determine the most lopsided trades in sports history.

It takes a long time to determine how a trade worked out. Only once all the players involved have completed their careers is it possible to fully determine the impact of the trade on each franchise. The most recent trade on this list occurred in 2013 between the Brooklyn Nets and Boston Celtics, when the Nets sent five players and four first-round picks to Boston in exchange for aging stars Paul Pierce, Kevin Garnett, and Jason Terry, as well as another player and two picks. Though the impact of these picks on the Celtics is still being borne out, we can safely say the Nets made a mess of the trade because all of the players they received were well past their prime. The Celtics, in turn, used some of those first-round picks in a trade to get Kyrie Irving.

Trades were selected based on how much a team incorrectly evaluated the potential production of a player they traded away or traded for. The overall value a player added was determined based on the number of productive years he had with his franchise, as well as statistics and honors such as All-star and Pro Bowl appearances.

Click here to see the worst trades in sports history.

1. Boston Red Sox & New York Yankees, 1919
> Boston traded: Babe Ruth
> New York traded: $100,000

It’s been nearly a century since the Boston Red Sox completed their sale of Babe Ruth to rivals New York Yankees — and to this day it’s considered one of the most famous and lopsided trades in sports history. Legend has it that Red Sox owner and theater producer Harry Frazee needed cash after one of his shows flopped, so he had to sell the slugger. Ruth was terrific in Boston, but after joining the Yankees, he blossomed into the greatest hitter in baseball history, shattering the all-time home run record and helping the Yanks win four championships — making his impact much greater than the $100,000 Boston sold him for.

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2. Chicago Cubs & St. Louis Cardinals, 1964
> Chicago traded: Lou Brock, Jack Spring, Paul Toth
> St. Louis traded: Ernie Broglio, Doug Clemens, Bobby Shantz

Intraleague rivals rarely trade players, and the Lou Brock trade is the perfect example of why. In 1964, the Cubs and Cardinals swapped three players apiece. The Cardinals traded pitcher Bobby Shantz, who was once the MVP, but his best years were behind him. Actually, all players involved in the deal had fairly short and unremarkable careers following the trade — except one. Lou Brock was a middling outfielder in Chicago, but he developed into the perfect leadoff hitter in St. Louis, raising his batting average significantly and leading the NL in stolen bases eight times in his Hall of Fame career.

3. Cincinnati Reds & Baltimore Orioles, 1965
> Cincinnati traded: Frank Robinson
> Baltimore traded: Jack Baldschun, Milt Pappas, Dick Simpson

Frank Robinson had been a star for a decade, but Cincinnati Reds management thought he was over the hill and traded him to the Baltimore Orioles, calling him “an old 30.” The next season, Robinson earned the AL Triple Crown — leading the league in batting average, home runs, and RBIs. He also won the AL MVP and helped the Orioles win the 1966 World Series. Robinson played in Baltimore for six seasons, making five All-Star teams and winning a second world title in 1970. None of the players he was traded for ever made an All-Star team in Cincinnati.

4. Philadelphia Phillies & Chicago Cubs, 1982
> Philadelphia traded: Ryne Sandberg, Larry Bowa
> Chicago traded: Ivan de Jesus

In 1982, the Philadelphia Phillies made the massive mistake of failing to recognize the potential of Ryne Sandberg. The year before, he played in a handful of games at age 21, hitting for only a .167 average. The Phillies shipped him and former All-Star shortstop Larry Bowa to the Chicago Cubs for Ivan de Jesus. De Jesus hit .249 in three years in Philadelphia. Sandberg played in Chicago for 15 years, racking up over 2,300 hits, 10 All-Star appearances, an MVP, and a spot in the Hall of Fame.

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5. San Francisco Warriors & Philadelphia 76ers, 1965
> San Francisco traded: Wilt Chamberlain
> Philadelphia traded: Connie Dierking, Paul Neumann, Lee Shaffer and cash

When a player is as great as Wilt Chamberlain, it’s difficult to get enough value when trading him. Chamberlain played for the San Francisco Warriors early in his career. The Warriors were low on money and had to deal their star player to the Philadelphia 76ers for three role players and cash. Chamberlain continued to dominate in Philly, winning his first NBA title there. He was part of another lopsided trade when the 76ers dealt him to the L.A. Lakers for three players. Yet the Warriors-76ers trade was more uneven, as Chamberlain was still in his prime in Philadelphia and the players the Lakers sent over were more successful than those in the trade from San Francisco.

6. New York Nets & Philadelphia 76ers, 1976
> New York traded: Julius Erving
> Philadelphia traded: $3 million

In 1976, the New York Nets wanted to join the NBA because the league the Nets played in, the ABA, folded. The NBA required ABA teams pay $3.2 million to join, and required an additional $4.8 million from the Nets because they were moving into the Knicks’ territory. To get the franchise into the NBA, the Nets had to sell their star player, Julius Erving, for $3 million to the Philadelphia 76ers. Dr. J became a superstar, while the Nets became an NBA laughing stock.

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7. Portland Trail Blazers & Buffalo Braves, 1976
> Portland traded: Moses Malone
> Buffalo traded: 1978 1st round pick

The Portland Trail Blazers’ trade of Moses Malone was a flop for two reasons: Malone was a three-time MVP and became a Hall of Famer; and just six days after the trade, Buffalo traded Malone for two first-round picks to the Houston Rockets. Portland seriously undervalued Malone both as a member of the team and a trade asset.

8. Los Angeles Lakers & Utah Jazz, 1979
> Los Angeles traded: Adrian Dantley
> Utah traded: Spencer Haywood

Adrian Dantley and Spencer Haywood have both been inducted into the Basketball Hall of Fame. In 1979, when they were traded for each other, Haywood’s career was winding down, while Dantley’s was just getting started. Haywood, who was battling a drug problem at the time, posted then-career lows in points and rebounds in Los Angeles. Dantley played seven seasons in Utah, making six All-Star teams.

9. Golden State Warriors & Boston Celtics, 1980
> Golden State traded: Robert Parish, 1st round pick
> Boston traded: Two 1st round picks

Trades, like the one in 1980 between the Warriors and Celtics, can often look worse in hindsight than they did at the time. Golden State sent Robert Parish and a first-round pick to Boston for two first-round picks. His first season in Boston, Parish earned his first of nine All-Star nods and first of four NBA championships. Golden State’s picks were Rickey Brown and Joe Barry Carroll, who have a combined one All-Star appearance. Carroll was picked first overall in 1980, two spots ahead of Boston’s pick, Kevin McHale — a seven-time All-Star and Hall of Famer.

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10. Vancouver Canucks & Boston Bruins, 1986
> Vancouver traded: Cam Neely, 1st round pick
> Boston traded: Barry Pederson

The Boston Bruins’ trade of Barry Pederson to Vancouver had long-lasting effects on the franchise. Pederson’s production in Vancouver never matched that of his early years in Boston. But his counterpart, Cam Neely, blossomed with the Bruins, making four All-Star teams and earning a spot in the Hockey Hall of Fame. The first-round pick in the deal was used on Glen Wesley, who was traded for more picks, which were then traded again over the years, eventually netting Boston Milan Lucic, who helped the Bruins win the 2011 Stanley Cup.

11. Tampa Bay Buccaneers & San Francisco 49ers, 1987
> Tampa Bay traded: Steve Young
> San Francisco traded: 2nd round pick, 4th round pick

After the Tampa Bay Buccaneers selected Steve Young first overall in the 1984 NFL Supplemental Draft, they expected a star. But Young, likely because of his supporting cast, struggled and posted a 3-16 record in the games he played his first two seasons. The Bucs bailed on Young, dealing him to San Francisco for the low price of a second- and a fourth-round pick. After quarterback Joe Montana left San Francisco, Young was the perfect successor, winning two MVPs and a Super Bowl.

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12. Minnesota Vikings & Dallas Cowboys, 1989
> Minnesota traded: Jesse Solomon, David Howard, Isaac Holt, 8 draft picks
> Dallas traded: Herschel Walker, 4 picks

One of the most infamous trades in sports history is the deal that sent running back Herschel Walker to Minnesota and kickstarted the Dallas Cowboys’ 1990s dynasty. Walker showed promise as a Cowboy, and the Vikings wanted to get better in a hurry, so they dealt a bevy of picks and players to get the running back. Walker never quite fit into the Vikings scheme and struggled in Minnesota. The Cowboys used the picks on players like Russell Maryland, Darren Woodson, and the NFL’s all-time rushing leader Emmitt Smith — cornerstone players of the three Super Bowls Dallas won in the 1990s.

13. Philadelphia Flyers & Quebec Nordiques, 1992
> Philadelphia traded: Peter Forsberg, Ron Hextall, Chris Simon, Mike Ricci, Kerry Huffman, Steve Duchesne, two first-round picks, $15 million
> Quebec traded: Eric Lindros

Center Eric Lindros lived up to his top overall pick promise, winning a Hart Trophy and earning a Hall of Fame spot. But to get him, the Flyers gave up $15 million, two first-round picks, and six players. Lindros was talented but struggled with concussions and missed many games. Peter Forsberg, just one of the six players Philly dealt to the Nordiques, ended up with similar production to Lindros and also won a Hart Trophy. Quebec, which relocated to Colorado not long after the trade, used the players and picks to win the Stanley Cup in 1996 and 2001.

14. Atlanta Falcons & Green Bay Packers, 1992
> Atlanta traded: Brett Favre
> Green Bay traded: 1st round pick

Before Brett Favre broke nearly every NFL passing record as a Green Bay Packer, he was languishing on the bench at the Atlanta Falcons as third-string QB. Favre was hampered by a hip injury, but new Packers General Manager Ron Wolf thought he would be successful and traded a first-rounder to get Favre — just a year after the Falcons drafted him with a second-rounder. Favre became an NFL legend, while the Falcons have yet to win a Super Bowl.

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15. Montreal Expos & Seattle Mariners, 1989
> Montreal traded: Randy Johnson, Gene Harris, Brian Holman
> Seattle traded: Mark Langston, Mike Campbell

Mark Langston was a promising young lefty pitcher in the 1990s. Montreal unfortunately gave up three players to get him, including Randy Johnson, one of the greatest left-handed pitchers of all time. Langston played in just 24 games as an Expo, while Johnson won a Cy Young and made five All-star teams in his time in Seattle.

16. Indianapolis Colts & St. Louis Rams, 1999
> Indianapolis traded: Marshall Faulk
> St. Louis traded: 2nd round pick, 5th round pick

Running backs tend to have a short shelf life in the NFL. This is likely why the Indianapolis Colts dealt Pro-Bowler Marshall Faulk to the St. Louis Rams for a second- and fifth-round pick. Faulk was reportedly motivated by the slight and responded by earning his first of three straight All-Pro designations and winning a Super Bowl with the “Greatest Show on Turf” Rams in 1999. He then won NFL MVP the year after.

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17. Montreal Canadiens & Colorado Avalanche, 1995
> Montreal traded: Patrick Roy, Mike Keane
> Colorado traded: Andrei Kovalenko, Martin Rucinsky, Jocelyn Thibault

After winning the 1993 Stanley Cup, Montreal seemed poised to continue winning. But goaltender Patrick Roy’s issues with management boiled over soon after, and he and Mike Keane were dealt to Colorado. None of the players the Canadiens received could make up for the loss of a great netminder. This move is widely considered as the one that closed Montreal’s championship window in the 1990s, while Roy and Keane helped Colorado win the 1996 Stanley Cup.

18. St. Louis Rams & Pittsburgh Steelers, 1996
> Los Angeles traded: Jerome Bettis, 3rd round pick
> Pittsburgh traded: 2nd round pick, 4th round pick

Though Jerome Bettis was a promising young running back in 1996, the Rams thought they could upgrade at the position. After taking RB Lawrence Phillips sixth overall in the 1996 NFL draft, St. Louis flipped Bettis and a third-rounder for a second- and fourth-rounder from the Pittsburgh Steelers. Phillips flamed out of the league after three seasons, but Bettis became a Steelers legend, making four Pro Bowls in Pittsburgh and winning a Super Bowl his final season.

19. Milwaukee Bucks & Dallas Mavericks, 1998
> Milwaukee traded: Dirk Nowitzki, Pat Garrity
> Dallas traded: Robert Traylor

Before the success of Dirk Nowitzki, European players had struggled to play well in the NBA. This may be one of the reasons why the Milwaukee Bucks had no issue trading Nowitzki and Pat Garrity for Robert Traylor out of the University of Michigan. Nowitzki played for 21 seasons, all for the Mavs. He made 14 All-Star teams, won an MVP and an NBA championship. Traylor struggled, playing for just seven seasons, averaging less than five points a game. The Mavs also used Garrity as a trade piece to acquire two-time MVP Steve Nash.

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20. New York Islanders & Ottawa Senators, 2001
> New York traded: Bill Muckalt, Zdeno Chara, 1st round pick
> Ottawa traded: Alexei Yashin

Alexei Yashin was a good young hockey player as an Ottawa Senator, though he had issues with management and was traded to the Islanders. In New York, Yashin could never find the form he had in Ottawa. Yet Zdeno Chara, who played sparingly as an Islander, played well in Ottawa, making two All-Star teams. The first-round pick the Islanders gave up for Yashin was used to select Jason Spezza, another great player for the Senators.

21. Boston Bruins & San Jose Sharks, 2005
> Boston traded: Joe Thornton
> San Jose traded: Brad Stuart, Marco Sturm, Wayne Primeau

To this day, Joe Thornton remains the only player in American pro sports history to be traded in the middle of an MVP season. The three players sent to Boston never made much of an impact — Brad Stuart and Wayne Primeau each played less than two full seasons for Boston, while Marco Sturm struggled with injuries. Thornton is still playing for the Sharks at a high level 14 years later.

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22. Florida Marlins & Detroit Tigers, 2007
> Florida traded: Miguel Cabrera, Dontrelle Willis
> Detroit traded: Dallas Trahern, Burke Badenhop, Frankie De La Cruz, Cameron Maybin, Andrew Miller, Mike Rabelo

After winning a World Series with the Florida Marlins in 2003, pitcher Dontrelle Willis and infielder Miguel Cabrera were the only players left from that team in 2007. The notoriously tight-fisted ownership refused to pay young players high salaries, instead trading them for prospects. Andrew Miller developed into a great reliever after leaving Florida in 2010, and few of the players Florida acquired made much of an impact. Willis struggled in Detroit, but Cabrera did not, becoming one of the greatest hitters of his generation, winning two MVPs as a Tiger.

23. Washington Redskins & St. Louis Rams, 2012
> Washington traded: 2012 1st round pick, 2012 2nd round pick, 2013 1st round pick, 2014 first round pick
> St. Louis traded: 2012 1st round pick

Had Robert Griffin III not injured his knee with the Redskins, this may have gone down as a worthwhile player to trade for. But Washington gave up three first-rounders and a second to acquire a player who did not pan out, hindering themselves for years to come. The Rams acquired LB Alec Ogletree, DT Michael Brockers, WR Stedman Bailey, RB Zac Stacy, RB Isaiah Pead, and OG Rokevious Watkins — most of whom became very productive players.

24. Cleveland Browns & Minnesota Vikings, 2012
> Cleveland traded: 1st round pick, 4th round pick, 5th round pick, 7th round pick
> Minnesota traded: 1st round pick

The Cleveland Browns made a lopsided and unnecessary trade to get Trent Richardson in 2012. The Alabama running back was highly touted but likely would have been available as the fourth pick, which Cleveland had. Minnesota, which had the third pick, did not need a running back with Adrian Peterson on its roster. The Browns sacrificed four picks for Richardson, then traded him near the start of his second season. Richardson is now known as an all-time draft bust.

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25. Brooklyn Nets & Boston Celtics, 2013
> Brooklyn traded: 5 players & first-round picks in 2014, 2016, 2017, and 2018
> Boston traded: Kevin Garnett, Paul Pierce, Jason Terry, D.J. White, 2017’s first and second round picks

The Brooklyn Nets mortgaged their future to acquire aging superstars in a misguided win-now approach. The Nets traded five role players and four first-round picks for Kevin Garnett, Paul Pierce, Jason Terry, D.J. White, and 2017’s first- and second-round picks. Garnett, Pierce, and Terry played for Brooklyn for less than two seasons each. The Nets were bounced from the NBA playoffs by the LeBron James-led Miami Heat. The Celtics used those picks on players like Jaylen Brown, as well as trading one to the Cavaliers for superstar Kyrie Irving.

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