Top 15 Worst Trades in MLB History

Trades are a routine part of professional baseball. Roster construction is a delicate balancing act that requires input from owners, general managers, managers, and the players themselves. Trades can be made for a variety of reasons, but every team seeks to improve with every acquisition that they make. In an ideal world, every trade would be mutually beneficial to both teams involved, however that is certainly not the case in the trades mentioned below.

Lopsided trades have been a part of baseball since the earliest days of the Major Leagues. Teams are constantly attempting to improve in order to compete for the World Series, while others look to stockpile prospects with a goal to succeed in the future. Whatever the reason a front office has for making a trade, it is always with the best interest of the team in mind. However, the effects of some of trades have left a lasting legacy on teams.

Several teams on the winning side of these trades have gone on to achieve greatness . World Series winners were made as a result of some of these deals. If the teams that traded future Hall of Famers away had known the greatness they possessed, it is unlikely they would have made the trades in the first place. Hindsight is always 20/20, but several of these deals appear much worse when viewed from a historical perspective.

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15 Jay Buhner for Ken Phelps

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Few trades are so lopsided that they have spawned their own Seinfeld jokes, but Yankees owner George Steinbrenner accomplished this with the trade of Buhner and Rick Balbon to the Seattle Mariners for Ken Phelps. Two years later, Phelps was moved for a minor leaguer, while Buhner had a solid big league career until 2001. Buhner hit over 300 home runs during his Major League career, which may have been the cause for Frank Costanza’s epic meltdown.

14 Mark McGwire for T.J. Mathews, Blake Stein, Eric Ludwick

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The Oakland Athletics made a huge mistake by trading Mark McGwire just before he would go on to make baseball history with the St. Louis Cardinals. McGwire was traded for several prospects, who never made an important impact. Meanwhile, McGwire would make baseball history with his 70 home run season in 1998 where he broke Roger Maris’ single season home run record. McGwire led the league in home runs the following season with 65 before he leveled off to numbers resembling a mere mortal. We won't begin to discuss the steroid issue here, as that's an issue for another time.

13 Jeff Bagwell for Larry Andersen

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The Houston Astros acquired the future of their franchise in exchange for relief pitcher Larry Andersen. Bagwell won the Rookie of the Year Award in his first season, and for the next fifteen years, he never looked back. He won an MVP Award in 1994 and made four All-Star Game appearances over the course of his career. Bagwell finished his career with a .297 average and 449 home runs and had his #5 retired by the Astros. What did Larry Andersen do for the Red Sox? He gave them a grand total of 22 innings where he gave up 3 runs.

12 Cliff Lee, Grady Sizemore, and Brandon Phillips for Bartolo Colon and Tim Drew

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When the Montreal Expos acquired Bartolo Colon in exchange for three players, they never dreamed that all three would go on to All-Star appearances. The Expos sent future Cy Young Award winner Cliff Lee, three-time All-Star Grady Sizemore, and three-time All-Star Brandon Phillips to the Cleveland Indians. All of the players involved in this trade continue their major league careers to this day, but the Expos were certainly losers in this deal as Colon only played one year with the Expos, going 10-4.

11 Jason Varitek and Derek Lowe for Heathcliff Slocumb

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The Boston Red Sox acquired two cornerstones of their 2004 World Series winning team by trading away clubhouse cancer Heathcliff Slocumb. Slocumb was a solid  closer for a period during the 1990s, but his skills quickly diminished. Varitek would go on to become the captain of the Red Sox and served them for his entire 14-year career. Lowe would go on to start and win Game 4 of the World Series for the Red Sox, forever sealing his place in baseball lore.

10 Miguel Cabrera and Dontrelle Willis for Cameron Maybin, Andrew Miller and Four Others

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Cameron Maybin and Andrew Miller have gone on to have successful Major League careers since being traded from Detroit to the Florida Marlins. However, if they had known they were trading away a future Triple Crown winner in Miguel Cabrera, they likely would have reconsidered. Miggy has won two MVP Awards and appeared in five more All-Star games since the trade in 2007, while the Marlins have continued to struggle since his departure. At the age of 31, Miggy still has several years left in his prime and the Marlins must continue to be kicking themselves for this deal.

9 Kenny Lofton for Ed Taubensee

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In 1991, the Houston Astros traded Kenny Lofton and Dave Rohde to the Indians in exchange for Willie Blair and Ed Taubensee. Blair and Taubensee both forged Major League careers for themselves, but were quickly eclipsed by Kenny Lofton, who developed in to one of the stars of the 1990s. Lofton went on the lead the league in stolen bases for the next five seasons and appear in six All-Star games following a runner-up finish in Rookie of the Year voting. Kenny Lofton now sits on the brink of the Hall of Fame and was a crucial part of several exciting Cleveland Indians teams.

8 Joe Nathan and Francisco Liriano for A.J. Pierzynski

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A.J. Pierzynski was a promising .300 hitting catcher when he was traded from Minnesota along with cash for Boof Bonser, Francisco Liriano, and Joe Nathan to San Francisco. Pierzynski played only one year in San Francisco, while Bonser, Liriano, and Nathan went on to be significant contributors to the Twins. Liriano has been dominant at times over the course of his Major League career, while Nathan has been one of the most consistent closers in the league over the last decade. Pierzynski went on to win the 2005 World Series with the Chicago White Sox, making the Giants big losers in this trade.

7 Frank Robinson for Milt Pappas, Jack Baldschun, and Dick Simpson

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After nearly a decade of productive seasons which saw Frank Robinson win Rookie of the Year and an MVP Award, Reds owner Bill DeWitt traded Robinson in 1965. In exchange for pitchers Milt “Gimpy” Pappas, Jack Baldschun, and outfielder Dick Simpson, Robinson was sent to the Baltimore Orioles. He wasted no time showing DeWitt that it was a mistake and produced perhaps the best offensive year of his career in 1966. Robinson helped the Orioles win the 1966 World Series and earned the Most Valuable Player award the same season.

6 Nolan Ryan and Three Others for Jim Fregosi

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When the New York Mets traded for six-time All-Star Jim Fregosi in exchange for several prospects, they believed that they were getting the better deal. One of those prospects turned out to be strikeout king Nolan Ryan. Ryan would go on to lead the league in strikeouts eleven times, while Fregosi would never make another All-Star Game appearance. Ryan went on to eight All-Star Game appearances and has had his number retired by the three other teams he played for during his career. Strangely enough, Fregosi went on to manage Ryan during his time with the California Angels.

5 John Smoltz for Doyle Alexander

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When John Smoltz was swapped to Atlanta from Detroit for Doyle Alexander in 1987, Alexander was at the tail end of a 19-year Major League career. Smoltz was only 20-years-old and the time, but it initially appeared that Detroit had gotten the better of the deal. Alexander finished 9-0 in his first season and went on to make the All-Star team the next summer. However, Smoltz would become the foundation of one of the most dominant pitching staffs in baseball history. Smoltz led the Braves to a decade of success and is the only pitcher in baseball history with at least 200 wins and 150 saves.

4 Lou Brock for Ernie Broglio

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Lou Brock and Ernie Broglio were the centerpieces of a six-player deal between the Chicago Cubs and the St. Louis Cardinals. Four months later Brock helped the Cardinals win the 1964 World Series with a seven-game victory over the New York Yankees. Two years later, he ended Maury Wills reign as the National League leader in stolen bases, a feat that he would accomplish eight times over the course of his career. Brock won another World Series in 1967 and was named to six  All-Star teams over the course of his Hall of Fame career. Broglio retired after the 1966 season and the deal is now considered one of the most lopsided in history.

3 Christy Mathewson for Amos Rusie

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In 1900, the Cincinnati Reds traded for Amos Rusie, one of the best strikeout pitchers of the 1890s, and sent a relatively unknown prospect from Pennsylvania named Christy Mathewson to the New York Giants in return. Rusie went 0-1 in the next season, his last in the Major Leagues. Mathewson went on to become known as the Christian Gentleman and helped the Giants win a World Series title. Mathewson was one of the “First Five” members of the Baseball Hall of Fame and is the only pitcher in the Top 10 for both career ERA and wins.

2 Pedro Martinez for Delino Deshields

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The Los Angeles Dodgers traded away a 22-year-old Pedro Martinez for infielder Delino DeShields. DeShields never batted above .300 or hit more than 11 home runs in any of his thirteen seasons in the Major Leagues, while Martinez developed into one of the most dominant pitchers of any era. Three years later Martinez won the first of his three career Cy Young Awards. Martinez went on to be a crucial part of the 2004 Boston Red Sox that won the World Series. Martinez is blessed by stat-heads as one of the best pitchers of the live-ball era, and he boasts the second highest winning percentage of any pitcher ever.

An honorable mention goes to the trade that Expos then made with the Red Sox, where they gave up Martinez for Carl Pavano and Tony Armas. Not as bad the first trade involving Pedro, but still pretty terrible.

1 Babe Ruth for $100,000

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Babe Ruth holds an indelible place in baseball lore as a crucial part of the Murderer’s Row lineup of the New York Yankees. Ruth initially played for Baltimore before he was purchased by the Boston Red Sox. Red Sox owner Harry Frazee was a theatrical producer that regularly needed money to finance his productions. This is still not 100% certain, but during one of those moments, he sold the greatest player in baseball history for $100,000 to finance No, No, Nanette. Ruth soon became one of the most prolific home run hitters in history and the Curse of the Bambino lasted until 2004.

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