Last Updated: June 17th, 2026 by Michael Schatz
Baseball history has seen some truly incredible trades that completely changed the fortunes of multiple franchises. From the infamous Babe Ruth deal to modern-era steals, these trades represent some of the most lopsided deals ever made in America’s pastime. Here’s a look at the 10 trades that general managers wish they could take back.
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1. The Curse Begins: Babe Ruth to the Yankees (1920)
In what’s considered the most infamous trade in sports history, the Boston Red Sox sold Babe Ruth to the New York Yankees for $100,000 and a $300,000 loan. This transaction forever changed baseball history, leading to the Yankees’ dynasty and the Red Sox’s 86-year World Series drought. Ruth went on to hit 714 home runs and led the Yankees to 7 World Series titles, while the Red Sox suffered through what became known as “The Curse of the Bambino.”
2. Cubs’ Colossal Mistake: Lou Brock for Ernie Broglio (1964)
The Chicago Cubs traded future Hall of Famer Lou Brock to the St. Louis Cardinals for pitcher Ernie Broglio in what became one of baseball’s most one-sided deals. Brock transformed into a Cardinals legend, stealing 938 bases and collecting 3,023 hits while leading St. Louis to two World Series championships. Meanwhile, Broglio won only seven more games before retiring in 1966, making this trade a perpetual source of Cubs fans’ nightmares.
3. Red Sox Regret: Jeff Bagwell for Larry Andersen (1990)
The Red Sox traded minor league prospect Jeff Bagwell to the Houston Astros for reliever Larry Andersen in a deadline deal they’d soon regret. Bagwell became one of the greatest first basemen in history, hitting 449 home runs with 1,529 RBIs and earning a spot in the Hall of Fame. Andersen pitched just 22 innings for Boston, making this trade one of the most lopsided deals in modern baseball history.
4. Reds’ Blunder: Frank Robinson for Milt Pappas (1965)
The Cincinnati Reds traded Frank Robinson to the Baltimore Orioles in a shocking move that immediately backfired. Robinson won the Triple Crown in his first season with Baltimore, leading them to two World Series titles. The players Cincinnati received – Milt Pappas, Jack Baldschun, and Dick Simpson – never came close to matching Robinson’s impact, making this one of the most regrettable trades in Reds history.
5. Tigers’ Loss: John Smoltz for Doyle Alexander (1987)
The Detroit Tigers traded prospect John Smoltz to the Atlanta Braves for veteran Doyle Alexander in a win-now move that proved costly. While Alexander helped Detroit make the playoffs that year, Smoltz became a Hall of Fame pitcher with 213 wins and 154 saves. His versatility as both a starter and closer made him one of the most valuable players in Braves history, while the Tigers lost a future cornerstone of their franchise.
6. Mets’ Mistake: Nolan Ryan for Jim Fregosi (1971)
The New York Mets traded away future legend Nolan Ryan to the California Angels for Jim Fregosi. Ryan went on to become one of baseball’s most dominant pitchers, throwing seven no-hitters and striking out an MLB-record 5,714 batters. Fregosi struggled in New York and was gone within two years, making this trade one of the most lopsided deals in baseball history.
7. Dodgers’ Disaster: Pedro Martinez for Delino DeShields (1993)
The Los Angeles Dodgers traded Pedro Martinez to the Montreal Expos for Delino DeShields in a move they’d immediately regret. Martinez developed into one of baseball’s most dominant pitchers, winning three Cy Young Awards and establishing himself as a Hall of Famer. DeShields hit just .241 in three disappointing seasons with the Dodgers before departing.
8. Phillies’ Folly: Ryne Sandberg and Larry Bowa for Ivan DeJesus (1982)
The Philadelphia Phillies traded future Hall of Famer Ryne Sandberg and Larry Bowa to the Chicago Cubs for Ivan DeJesus. Sandberg became a Cubs legend, earning 10 All-Star selections and nine Gold Gloves while revolutionizing second base play. DeJesus spent just three unremarkable seasons with the Phillies, making this trade one of the most lopsided in Philadelphia sports history.
9. Twins’ Terrible Decision: Releasing David Ortiz (2002)
While technically not a trade, the Minnesota Twins’ decision to release David Ortiz ranks among baseball’s worst personnel moves. Ortiz signed with the Boston Red Sox and became one of baseball’s most clutch hitters, leading Boston to three World Series titles while hitting 541 career home runs. His transformation into “Big Papi” made this move particularly painful for Twins fans.
10. Reds’ Ancient Blunder: Christy Mathewson for Amos Rusie (1900)
The Cincinnati Reds traded Christy Mathewson to the New York Giants for Amos Rusie in one of baseball’s earliest lopsided deals. Mathewson became one of baseball’s greatest pitchers, winning 373 games and leading the Giants to five National League pennants. Rusie pitched just three games before retiring, making this trade a historic mistake that still resonates over a century later.