Trades and transfers are the heartbeat of Major League Baseball, where a single deal can transform a team’s fortunes—or leave fans shaking their heads for decades. While some trades go down in history as genius moves, others become cautionary tales of what might have been.
In this article, we dive into the most infamous trades in MLB history—moments where bold decisions backfired spectacularly, reshaping the game and the teams involved in ways no one saw coming.
14. Oakland Athletics Trade Jose Canseco to the Texas Rangers
The Oakland Athletics traded Jose Canseco to the Texas Rangers on August 31, 1992, in exchange for Ruben Sierra, Jeff Russell, Bobby Witt, and cash. This trade is often regretted as Canseco was a dominant force, leading all Major League players with 230 home runs from 1986-92 and earning the 1988 MVP award. Despite his later injuries, Canseco’s departure marked a significant loss for the Athletics.
13. Baltimore Orioles Trade Curt Schilling to the Houston Astros
On January 10, 1991, the Baltimore Orioles traded Curt Schilling, Pete Harnisch, and Steve Finley to the Houston Astros for Glenn Davis. This trade is often cited as one of the most unbalanced in MLB history. Schilling went on to become a dominant pitcher, while Davis struggled with injuries.
12. Atlanta Braves Trade Mark Teixeira to the Los Angeles Angels
The Atlanta Braves traded Mark Teixeira to the Los Angeles Angels in 2008 for Casey Kotchman and minor league pitcher Stephen Marek. Teixeira, a Gold Glove first baseman, was a significant loss for the Braves, who failed to secure a long-term deal with him. The Angels, meanwhile, bolstered their lineup with Teixeira’s power and defensive skills.
11. Arizona Diamondbacks Trade Max Scherzer to the Detroit Tigers
The Arizona Diamondbacks trading Max Scherzer to the Detroit Tigers in 2009 is one of the most regrettable trades in MLB history. Scherzer, drafted 11th overall by the Diamondbacks in 2006, was traded along with Daniel Schlereth for Edwin Jackson and Ian Kennedy. Scherzer went on to win three Cy Young Awards and two World Series titles, cementing his status as one of the greatest pitchers of his generation.
10. Cleveland Indians Trade Roger Maris to the Kansas City Athletics
The Cleveland Indians traded Roger Maris to the Kansas City Athletics in 1958, a move that would haunt them for decades. Maris, who would go on to hit 61 home runs in 1961, was traded along with Dick Tomanek and Preston Ward for Vic Power and Woodie Held. This trade is often cited as one of the worst in MLB history, given Maris’s subsequent success with the Yankees.
9. Houston Astros Trade Ben Zobrist and Mitch Talbot to the Tampa Bay Devil Rays
The Houston Astros traded Ben Zobrist and Mitch Talbot to the Tampa Bay Devil Rays for Aubrey Huff in 2006. This trade is often regretted as Zobrist went on to have a versatile and successful career, playing multiple positions and winning a World Series with the Chicago Cubs. Meanwhile, Huff’s time with the Astros was short-lived and less impactful.
8. New York Mets Trade Scott Kazmir and Jose Diaz for Victor Zambrano and Bartolome Fortunato
The Mets traded away top pitching prospect Scott Kazmir and Jose Diaz for Victor Zambrano and Bartolome Fortunato in 2004. Kazmir gave the Rays four solid seasons, including a 2008 division title and World Series run. Meanwhile, Zambrano was a complete bust, plagued by injuries and control issues, and Fortunato had a brief, unimpressive career.
7. St. Louis Cardinals Trade Adolis GarcÃa for Cash Considerations
The St. Louis Cardinals traded Adolis GarcÃa to the Texas Rangers for cash considerations in 2019. GarcÃa, now known as “El Bombi,” went on to become the American League Championship Series MVP in 2023, showcasing his power and improvement over time. The Cardinals’ decision to let him go for minimal return is now seen as a significant mistake.
6. Chicago Cubs Trade Eloy Jiménez and Dylan Cease to the Chicago White Sox
The Chicago Cubs traded Eloy Jiménez and Dylan Cease to the Chicago White Sox for José Quintana in 2017. This trade has been widely criticized as one of the worst in recent MLB history. Jiménez has shown significant power despite injury issues, while Cease has become a dominant force, finishing 2nd in the 2022 American League Cy Young voting with a 2.20 ERA and 227 strikeouts.
5. Colorado Rockies Trade Nolan Arenado to the St. Louis Cardinals
The Colorado Rockies traded Nolan Arenado to the St. Louis Cardinals in 2021, a move that has been heavily criticized. The Rockies received several prospects and sent $50 million to St. Louis to offset Arenado’s contract. Arenado has since expressed relief over the trade, stating he has “moved on” and appreciates his new team.
4. Red Sox Trade Jeff Bagwell to the Houston Astros
The Boston Red Sox traded Jeff Bagwell to the Houston Astros for Larry Andersen in 1990, a move considered one of the most lopsided trades in baseball history. Bagwell went on to have a Hall of Fame career with the Astros, hitting .297 with 449 home runs and 1,529 RBIs.
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3. Cubs Trade Lou Brock to the St. Louis Cardinals
The Chicago Cubs made one of the most infamous trades in MLB history by sending Lou Brock to the St. Louis Cardinals in 1964. In exchange, they received Ernie Broglio, who was hampered by injuries and won only seven more games before retiring. Brock, meanwhile, became a Hall of Fame outfielder, winning three National League pennants and two World Series with the Cardinals, and setting a then-record 938 stolen bases.
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2. Red Sox Trade Mookie Betts to the Dodgers
The Boston Red Sox traded Mookie Betts and David Price to the Los Angeles Dodgers in 2020, a move that has been widely criticized. Betts, a former MVP, signed a 12-year, $365 million contract with the Dodgers shortly after the trade. The Red Sox received Alex Verdugo, Jeter Downs, and Connor Wong in return, but the loss of Betts’ talent and the financial burden of Price’s contract have made this trade a regrettable one for Boston.
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1. Red Sox Trade Babe Ruth to the Yankees
The 1920 trade of Babe Ruth from the Boston Red Sox to the New York Yankees is often cited as the worst trade in MLB history. Red Sox owner Harry Frazee sold Ruth for $100,000, a deal that included a $350,000 loan from Yankees co-owner Jacob Ruppert, secured by a mortgage on Fenway Park. This transaction marked the beginning of an 86-year championship drought for the Red Sox, popularizing the “Curse of the Bambino” superstition. The Yankees, meanwhile, won seven AL pennants and four World Series with Ruth.
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