In Hindsight, Are These The 20 Worst Trades In MLB History?

In Hindsight, Are These The 40 Worst Trades In MLB History? They Were All So Horrible - Brake For It
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In Hindsight, Are These The 40 Worst Trades In MLB History? They Were All So Horrible
Todd Neikirk | Sports | 14 Apr 2026
Sometimes, a trade is successful and fair for both teams. But more often than not, one team will do better than the other as the result of a trade. Lopsided trades can happen for a number of reasons, and there have been many throughout the history of the MLB.
Keep reading for a list of the most one-sided trades of all time.
1910 - Joe Jackson To The Indians
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Back in 1910, the Philadelphia Athletics gave up one of their most promising players. They traded their players Morrie Rath and Joe Jackson in exchange for the Cleveland Naps's (now renamed the Cleveland Indians) Bris Lord.
While Lord made a decent 6.6 WAR in three seasons, Jackson achieved .375, .441, and .542 in his six seasons with the Indians. In 1915, he joined the Chicago White Sox, where he helped them win the American League pennant and the World Series. Jackson is now nicknamed "Shoeless" Joe Jackson.
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1919 - Babe Ruth To The Yankees
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The most famous lopsided trade in baseball history is also one of its oldest. Babe Ruth was a 2-way star as an Outfielder and a Pitcher, but Red Sox Owner Harry Frazee needed money to finance a theater production.
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He sold Ruth to the hated Yankees, which ended up paying off big for the team. Ruth led the Yanks to 4 World Series, and the Red Sox took 86 years to win their next one.
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1960 - Rocky Colavito To The Tigers
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In 1959, outfielder Rocky Colavito hit four consecutive home runs in one game playing for the Cleveland Indians. The team decided to trade him for Harvey Kuenn the following year, and "The Colavito Curse" began. As a Tiger, Colavito smashed 159 home runs in four seasons.
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He was an All-Star for six seasons hit over 40 home runs for three seasons. On the other hand, the Indians sunk to the bottom half of the A.L. East and stayed there for a painful 30 seasons.
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1964 - Lou Brock To The Cardinals
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In the early 1960s, Lou Brock was a promising right fielder who played for the Chicago Cubs. But after he only hit a .260 average over two seasons, they gave up on him. They traded Brock to the St. Louis Cardinals in exchange for the National League player Ernie Broglio. Afterward, Broglio only managed 3.5 WAR and .689 OPS in four seasons.
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Four months after Brock joined the Cardinals, the team won the 1964 World Series. In 1974, he broke the record for the most stolen bases--118 in a single season. Throughout his 16 seasons with the Cardinals, Brock stole 888 bases with a .761 OPS and 41.6 WAR.
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1966 - Frank Robinson To The Orioles
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Despite many years of superstar production, the Reds thought Frank Robinson was getting long in the tooth. They traded the star to the Baltimore Orioles in 1966 for a package led by Milt Pappas. It turned out Robinson was far from done.
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Robinson continued to be a major star for the Orioles and Pappas never quite reached his supposed potential. The Outfielder became the leader for a Baltimore team that would capture the 1970 World Series.
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1971 - George Foster To The Reds
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Left fielder George Foster was one of the best right-handed sluggers of his time, playing for the San Francisco Giants the same time as Willie Mays. Just as his third season with the Giants was starting, the team traded him to the Cincinnati Reds for shortstop Frank Duffy and pitcher Vern Geishert.
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As soon as he got to Cincinnati, their center fielder tore his Achilles and Foster joined the starting line-up. It took him some time for Foster to find his rhythm, but in 1976 he was hitting .343 and ended the season with 29 home runs and led the major league in RBIs at 121.
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1972 - Steve Carlton To The Phillies
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Steve Carlton played for the St. Louis Cardinals in the late 1960s, including their 1967 World Series win. In 1971, Carlton was struggling with a salary dispute. The Cardinals traded Carlton for the Phillies' pitcher, Rick Wise. At the time, it made sense, but it's now considered one of the most lopsided trades in history.
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In his Phillies uniform, Carlton won four Cy Young Awards and ended up in the Baseball Hall of Fame. His pitching was so vicious that slugger Willie Stargell compared it to "trying to drink coffee with a fork." Wise, however, didn't stay with the Cardinals.
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1972 - Sparky Lyle To The Yankees
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The Boston Red Sox selected pitcher Sparky Lyle as a first-year draft pick in 1964, playing in the farm system. Once they called him up and made him a relief pitcher, Lyle saved 64 games over four years. In 1972, the Red Sox made the mistake of trading him to the Yankees.
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Pitching for the Yankees, Lyle established himself as one of the greatest relief pitchers of the '70s. He broke Hoyt Wilhelm's American League record of 154 career saves and claimed the Cy Young Award in 1977. The player they traded him for, Danny Carter, ended his career in 1976.
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1972 - Nolan Ryan To The Angels
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The Mets of the late 60's and early 70's had a pitching staff that boasted tremendous talent including Nolan Ryan. The team figured they had enough pitching talent with Tom Seaver and Jon Matlack. Beside, Ryan could barely hit the broadside of a barn.
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Once he reached Los Angeles, though, Ryan began to harness his amazing stuff and became a superstar. He pitched for the Angels for eight seasons, made 5 All-Star games and recorded a boatload of strikeouts.
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1982 - Ryne Sandberg To The Cubs
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During the 1981 season, Philadelphia realized they had a raw prospect in Ryne Sandberg who didn't necessarily have a position. Wanting to acquire a more veteran player, the Phillies traded Sandberg to the Cubs for Ivan De Jesus.
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De Jesus was a decent fielding Shortstop with a light bat. Sandberg went over to Chicago, became a Second Baseman and an immediate superstar. Sandberg became a legendary player for the Cubs and was elected into the Baseball Hall of Fame in 2005.
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1983 - Keith Hernandez To The Mets
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Keith Hernandez was a star-level player who won an MVP Award and a World Series title in 1982 while in St. Louis. The First Baseman was traded to the Mets.
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In 1986, Hernandez captained the Mets to the World Series title. The best player St. Louis received in return, pitcher Neil Allen, had an unspectacular career and was gone from the Cardinals by 1985.
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1984 - Willie Hernandez To The Tigers
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In 1984, Willie Hernandez was an unremarkable relief pitcher for the Philadelphia Phillies. The team traded him to the Detroit Tigers in exchange for Glenn Wilson and John Wockenfuss. In the Tigers uniform, Hernandez flourished.
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Hernandez helped the Tigers ascend to the 1984 world series. He won both Most Valuable Player and the American League Cy Young award that same year. Overall, he pitched 140.3 innings with 32 saves and 1.92 ERA. Meanwhile, the Phillies only managed 81-81 with 3.63 ERA from their players.
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1987 - John Smoltz To The B…

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