MLB teams will be wheeling and dealing this offseason as they look to upgrade their rosters heading into 2025. Last offseason, we saw a blockbuster deal where the New York Yankees acquired Juan Soto from the San Diego Padres, which has paid off for both teams. Soto helped the Yankees reach the World Series while Michael King is turning into an ace for the Padres. San Diego also used a prospect in the trade to acquire pitcher Dylan Cease.
However, many trades have set franchises back years. Here’s a look at the 12 worst trades of all time.
Oakland Athletics trade Mark McGwire to St. Louis Cardinals (July 1997)
The Oakland A’s traded All-Star slugger Mark McGwire to the St. Louis Cardinals for three pitchers — Eric Ludwick, T.J. Mathews, and Blake Stein. In five seasons with the Cardinals, McGwire hit 220 home runs and broke Roger Maris’ all-time single-season home run record in 1998 with 70 home runs. The return for Oakland? Ludwick and Stein won six games combined, while Mathews posted a 4.78 ERA in five seasons.
Related: MLB insider calls this All-Star’s contract a ‘monster mistake’ by St. Louis Cardinals
Montreal Expos trade Randy Johnson to Seattle Mariners (May 1989)
The Montreal Expos traded Randy Johnson, Gene Holman, and Brian Holman to the Seattle Mariners for pitchers Mark Langston and Mike Campbell. During his ten seasons in Seattle, Johnson became one of baseball’s premier pitchers, winning a Cy Young Award and making five All-Star teams. Langston made just 24 starts for the Expos before departing for the California Angels, while Campbell never threw a pitch for Montreal.
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New York Mets trade Nolan Ryan to California Angels (December 1971)
The New York Mets gave up on Nolan Ryan way too early. The Mets shipped Ryan to the California Angels for All-Star infielder Jim Fregosi. While Fregosi lasted less than two seasons in Queens, Ryan became one of baseball’s greatest pitchers, retiring with the most strikeouts (5,714) and no-hitters (7) in MLB history. The Mets missed out on a potential dominant duo of Ryan and Tom Seaver.
San Diego Padres trade Ozzie Smith to St. Louis Cardinals (December 1981)
The San Diego Padres traded Ozzie Smith and two others to the St. Louis Cardinals for Garry Templeton, Sixto Lezcano, and Luis DeLeon. Smith became a Hall of Famer and baseball’s greatest defensive shortstop, winning 13 Gold Gloves. He played in three World Series for the Cardinals, winning one championship.
Related: MLB insider calls this All-Star’s contract a ‘monster mistake’ by St. Louis Cardinals
Chicago White Sox trade Fernando Tatis Jr. to San Diego Padres (June 2016)
Maybe the Chicago White Sox wouldn’t have lost a record 121 games if they didn’t part with Fernando Tatis Jr.? Looking for pitching during the 2016 season, the White Sox shipped Tatis to the San Diego Padres for James Shields. In three seasons with Chicago, Shields went 16-35 with a 5.31 ERA and 79 ERA+. Meanwhile, Tatis became the Padres’ franchise cornerstone, earning two All-Star selections and two top-five MVP finishes, despite missing 2022 due to injury and suspension.
Philadelphia Phillies trade Ryne Sandberg to Chicago Cubs (January 1982)
The Philadelphia Phillies could have had one of the greatest infields ever with Mike Schmidt and Ryan Sandberg. However, that didn’t come to fruition as the Phillies sent Sandberg and Larry Bowa to the Chicago Cubs for shortstop Iván de Jesús. Sandberg crafted a Hall of Fame career in Chicago, while de Jesús spent three unremarkable seasons in Philadelphia, hitting .249/.319/.319 with just seven home runs. Ouch.
Los Angeles Dodgers trade Pedro Martinez to Montreal Expos (October 1993)
It’s hard to imagine the Los Angeles Dodgers making a bad trade with the way the franchise is run today, but it actually happened decades ago. In October 1993, the Dodgers traded Pedro Martinez — who went 10-5 with a 2.61 ERA — to the Montreal Expos for Delino DeShields. It’s safe to say the Dodgers would’ve liked a do-over on that one. Martinez blossomed into a dominant force in Montreal, winning the 1997 Cy Young Award. He later won two more Cy Young Awards with the Boston Red Sox, helped secure the 2004 World Series championship, and entered the Hall of Fame in 2015.
Related: Boston Red Sox trading two young players in offseason, including All-Star?
Chicago Cubs trade Lou Brock to St. Louis Cardinals (June 1964)
The Chicago Cubs dealt Lou Brock to the St. Louis Cardinals as part of a six-player deal. It’s safe to say the Cardinals fleeced the Cubs. Chicago got back in the trade pitcher Ernie Broglio (who won only seven games with the Cubs before retiring in 1966), Bobby Shantz, and Doug Clemens. All Brock would go on to do is accumulate 3,023 hits, steal 938 bases (second all-time), win two World Series, and get inducted into the Hall of Fame in 1985.
Detroit Tigers trade John Smoltz to Atlanta Braves (August 1987)
The Detroit Tigers traded minor league pitcher John Smoltz to the Atlanta Braves for Doyle Alexander. While Alexander helped Detroit reach the 1987 ALCS, Smoltz built a Hall of Fame career in Atlanta, becoming the only pitcher in MLB history with at least 200 wins and 150 saves. He also won a World Series championship with the Braves in 1995.
Related: New Atlanta Braves rumor links team to pursuit of big time power bat in free agency this winter
Boston Red Sox trade Jeff Bagwell to Houston Astros (August 1990)
Despite being one of the more popular franchises in the game, the Boston Red Sox have made some mind-boggling trades over the years. In August 1990, the Red Sox were looking for bullpen help down the stretch, so they sent then-minor leaguer Jeff Bagwell to the Houston Astros for reliever Larry Andersen. He only lasted one month with the Red Sox before signing with the San Diego Padres that offseason. On the other hand, Bagwell went on to play 15 seasons in Houston, hitting 449 home runs, 488 doubles, with a .948 OPS, and 149 OPS+. He was NL Rookie of the Year in 1991, NL MVP in 1994, and a Hall of Famer in 2017.
Related: Will Houston Astros trade multiple All-Stars this offseason to lower payroll?
Florida Marlins trade Miguel Cabrera to Detroit Tigers (December 2007)
The Florida Marlins sure loved blowing up their teams. In December 2007, the Marlins shipped Miguel Cabrera, one of the greatest right-handed hitters of all-time, and southpaw Dontrelle Willis to the Detroit Tigers for six players, headlined by outfielder Cameron Maybin and pitcher Andrew Miller. Maybin played four total seasons with the Marlins, accumulating a 2.7 WAR. Miller would go 10-20 with a 5.89 ERA as a starter, before finding success as a reliever elsewhere. Cabrera, on the other hand, hit 373 home runs, accumulated 2,332 hits, won the AL Triple Crown in 2012, and was a two-time AL MVP.
Related: How the ‘spirit of this team’ led Detroit Tigers to improbable postseason appearance
Boston Red Sox trade Mookie Betts to Los Angeles Dodgers (February 2020)
It will never make sense why the Boston Red Sox traded one of the greatest players of our generation. The Red Sox essentially traded Betts to lower their payroll and they haven’t been the same since. In February 2020, right before the world stopped because of COVID-19, Boston shipped Betts and pitcher David Price to the Los Angeles Dodgers for Alex Verdugo, Jeter Downs, and Connor Wong. Of the players the Red Sox received, Wong is the only one left. Meanwhile, Betts has won two World Series with the Dodgers, while hitting 132 home runs, 142 doubles, scored 458 runs, with a .902 OPS, and 145 OPS+. He’s well on his way to the Hall of Fame.
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Boston Red Sox trade Babe Ruth to New York Yankees (January 1920)
It’s undoubtedly the worst trade of all-time. In January 1920, the Boston Red Sox sent Babe Ruth to the New York Yankees for $100,000. Why did Boston trade “The Great Bambino”? According to the Baseball Hall of Fame, Ruth, who was an excellent pitcher at the time, didn’t want to pitch anymore and just play the outfield exclusively. He also demanded a contract at the beginning of 1919. With that, Ruth was traded to the Yankees and baseball was never the same again. Of his 714 home runs, 659 of them came with the Yankees. He also led the Bronx Bombers to four championships and formed the greatest hitting duo ever with Lou Gehrig.
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