Major League Baseball has witnessed countless trades over the years, but some have become infamous due to their disastrous outcomes. Whether it’s the trade of a future Hall of Famer or a missed opportunity that set a franchise back for years, these deals serve as cautionary tales.
Let’s break down the 10 worst MLB trades in history—moves that forever altered the fate of teams and players alike.
10. Pedro Martinez – Expos to Red Sox (1994)
In one of the most head-scratching moves in baseball, the Boston Red Sox traded a young Pedro Martinez from the Montreal Expos in 1994. While Martinez had shown flashes of brilliance with the Expos, Boston traded him in for Tony Armas Jr. and Carl Pavano.
Martinez would go on to become a three-time Cy Young winner and one of the best pitchers of of all time. Montreal’s failure to keep him remains one of the most painful missteps in MLB history with the Expos relocating to Washington in 2004, the same year the Red Sox and Martinez won the World Series.
9. Frank Robinson – Reds to Orioles (1965)
In one of the most bizarre trades in baseball history, the Cincinnati Reds traded Frank Robinson, a future Hall of Famer, to the Baltimore Orioles for Milt Pappas, Jack Baldschun, and Dick Simpson in 1965.
Robinson, one of the most feared hitters of his time, would go on to win the MVP award in his first season with the Orioles and lead the team to a World Series title. Meanwhile, the Reds got little value in return, and Robinson’s dominance for years to come served as a painful reminder of the trade’s disastrous consequences.
8. Randy Johnson – Mariners to Astros (1989)
The Seattle Mariners’ decision to trade Randy Johnson to the Houston Astros in 1989 for three minor league players is still remembered as one of the worst MLB trades in the history of the franchise. He would eventually join the Arizona Diamondbacks after 11 regular season starts in Houston.
Johnson went on to become one of the most dominant pitchers in MLB history, earning five Cy Young awards and leading the Diamondbacks to a World Series title in 2001. The Mariners, on the other hand, never came close to that level of success, while Johnson’s brilliance continued to haunt them for years.
7. Roger Maris – Athletics to Yankees (1959)
In 1959, the Kansas City Athletics traded Roger Maris to the New York Yankees for a package that included seven players r. Maris, who would go on to break Babe Ruth’s single-season home run record in 1961, became a cornerstone of the Yankees’ lineup.
His power and clutch performances helped the Yankees win three World Series championships. The Athletics, however, did not benefit from this trade and were left regretting their decision as Maris solidified his place in baseball lore.
6. Nolan Ryan – Mets to Angels (1971)
The New York Mets’ decision to trade Nolan Ryan to the California Angels in 1971 is a classic example of underestimating a young talent. Ryan, who was shipped off in a package that brought back Jim Fregosi, would go on to become one of the most iconic pitchers in baseball history.
Ryan earned a record seven no-hitters and a spot in Cooperstown with Hall of Fame induction in 1999. Fregosi’s time with the Mets was disappointing, while Ryan’s career took off in a way few could have predicted, making this deal a stunning blunder in New York’s history.
5. John Smoltz – Tigers to Braves (1987)
In one of the most lopsided trades of the 1980s, the Atlanta Braves acquired a 20-year old John Smoltz from the Detroit Tigers in exchange for 36-year old veteran pitcher Doyle Alexander in 1987. While Alexander had a strong half-season with the Braves, it was Smoltz who went on to become a Hall of Fame pitcher.
Smoltz was part of the Braves’ dominant pitching rotation during the 1990s, helping the team win multiple division titles and a World Series in 1995. This trade proved to be a disaster for the Tigers, who watched Smoltz blossom into one of the greatest pitchers of his generation.
4. Lou Brock – Cubs to Cardinals (1964)
The Chicago Cubs’ decision to trade Lou Brock to the St. Louis Cardinals in a deal which included pitcher Ernie Broglio in 1964 has since become one of the most infamous trades in MLB history. Brock, a Hall of Famer, went on to become an all-time great base stealer and helped the Cardinals win a World Series title in 1964.
Although the deal initially looked like it favored the Cubs, Broglio’s time in Chicago was short and underwhelming, making this trade a painful reminder of how a miscalculation in player evaluation can drastically impact a franchise.
3. Jay Buhner – Yankees to Mariners (1988)
In a deal that remains a staple in the worst MLB trades of all time discussions, the New York Yankees traded Jay Buhner to the Seattle Mariners for pitcher Kevin Brown in 1988. Buhner would go on to hit 310 career home runs and become a fan favorite in Seattle, while Brown’s career never matched the expectations set for him in New York.
This trade was a major misstep for the Yankees, as Buhner’s power and consistency with the Mariners provided a lasting legacy for Seattle entering the franchise’ Hall of Fame, while Brown contributed little in comparison.
2. Mark McGwire – Athletics to Cardinals (1997)
In 1997, the Oakland Athletics traded Mark McGwire to the St. Louis Cardinals for T. J. Mathews, Eric Ludwick and Blake Stein – mostly young prospects. While McGwire’s power had already been established, the Cardinals got more than they bargained for when McGwire went on to break the single-season home run record in 1998, hitting 70 homers.
McGwire’s performance revitalized the Cardinals and helped push them into the postseason. The Athletics, meanwhile, saw little return on the trade, making this one of the most lopsided moves in recent memory.
1. Babe Ruth – Red Sox to Yankees (1919)
Arguably the most infamous trade in MLB history, the Boston Red Sox’s decision to sell Babe Ruth to the New York Yankees in 1919 is widely considered the worst trade in baseball history. Ruth, the most iconic player of his era, would go on to lead the Yankees to an unprecedented run of success, winning multiple World Series and forever changing the landscape of baseball.
The Ruth deal altered the history of the MLB. Meanwhile, the Red Sox entered a drought that lasted 86 years before winning another World Series title. Ruth’s departure is often cited as the beginning of the “Curse of the Bambino,” a stark reminder of how one trade can shape the future of a franchise for generations.
Conclusion: The Worst Trades in MLB History
These trades represent some of the most egregious blunders in baseball history. From Babe Ruth’s legendary departure to Lou Brock’s untimely exit from Chicago, each of these moves altered the course of MLB history in a dramatic way.
While some teams recovered, many never fully bounced back from the fallout of these decisions. Whether driven by poor player evaluation, financial reasons, or simple bad luck, these trades are cautionary tales for future general managers, reminding us all that the stakes in baseball deals are higher than most ever imagine.
