The 25 Worst Baseball Trades of the Last 25 Years

Zak SchmollAnalyst IMay 11, 2012

The 25 Worst Baseball Trades of the Last 25 Years

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    Every season, many general managers make trades hoping to make their respective franchises better. That is a noble goal, but trades don't always work out. In fact, some trades seem so lopsided in retrospect that you wonder what on earth that general manager must have been thinking.

    To be fair, hindsight is 20-20. It is a lot easier for me to look back and criticize than it is for that general manager to predict how talented a prospect will actually become or how quickly a veteran will fade.

    Therefore, since we have the ability of hindsight, we are going to be looking at the long-term impact of the trade. In other words, trading a future superstar for a borderline veteran who was only useful for one season is a bad thing in my book.

    Twenty-five trades in the past 25 years stand out above the rest as particularly questionable by my terms. If I have forgotten some major trade, feel free to leave a comment.

25. The Infamous Alex Rodriguez-Alfonso Soriano Trade (2004)

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    New York Yankees receive Alex Rodriguez and cash

    Texas Rangers receive Alfonso Soriano and Joaquin Arias

    I had to put this trade on this list for a few reasons. First of all, the Texas Rangers should not have traded away the best player in baseball even though he was saddled with probably the worst contract in baseball.

    From the New York Yankees' perspective, why would they take on the worst contract in baseball? I realize that they have a lot of money, but at some point, even the Yankees need to exercise some restraint.

    This trade worked out pretty well for both teams in retrospect, but the simple fact that the Rangers were willing to trade the best player in baseball below market value and the fact that the Yankees were willing to take on such a ridiculous contract make this one of the worst trades in recent memory.

24. Jose Contreras Moves to Chicago (2004)

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    Chicago White Sox receive Jose Contreras and cash

    New York Yankees receive Esteban Loaiza

    Jose Contreras made an excellent debut with the New York Yankees, and he went on to have three very successful years with the White Sox. On the other hand, Loaiza only pitched half a season for the Yankees and posted an 8.50 ERA.

    Contreras is by no means a Hall of Famer, but in this trade he was an incredible bargain, and he is still having some success out of the bullpen for the Philadelphia Phillies today.

23. Scott Kazmir Arrives in Tampa Bay (2004)

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    Tampa Bay Devil Rays receive Scott Kazmir and Jose Diaz

    New York Mets receive Victor Zambrano and Bartolome Fortunato

    Although Scott Kazmir didn't quite pan out in the long run, the short-term results speak for themselves. Kazmir helped Tampa Bay become a serious contender again and appear in the 2008 World Series. On the other hand, Zambrano ended up with a losing record as a member of the New York Mets.

    I know that I mentioned in the beginning that we are looking at the long-term implications of these swaps, but Kazmir helped build a winning atmosphere in Tampa Bay that still exists even though he is no longer pitching in Major League Baseball.

22. Jermaine Dye Becomes a Royal (1997)

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    Kansas City Royals receive Jermaine Dye and Jamie Walker

    Atlanta Braves receive Keith Lockhart and Michael Tucker

    Jermaine Dye developed into an All-Star outfielder with the Kansas City Royals as he started driving in runs and hitting the ball out of the park. Jamie Walker was also a serviceable relief pitcher for quite a long time.

    In return, the Kansas City Royals sacrificed a utility infielder in Lockhart and a decent all-around outfielder in Tucker. That does not quite equal the All-Star talent they traded away that year.

21. Shin-Soo Choo Is Swapped for Ben Broussard (2006)

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    Cleveland Indians receive Shin-Soo Choo and Shawn Nottingham

    Seattle Mariners receive Ben Broussard and cash

    Ben Broussard had a decent career with the Cleveland Indians, but he was not the same after he was traded away. On the other hand, Shin-Soo Choo has developed into a solid outfielder who is always capable of going 20-20.

    At the time, this trade seemed relatively balanced, but when you look back, this was not a wise move on the part of the Seattle Mariners.

20. Adrian Gonzalez Becomes a Force in San Diego (2006)

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    San Diego Padres receive Adrian Gonzalez, Chris Young and Terrmel Sledge

    Texas Rangers receive Adam Eaton, Billy Killian and Akinori Otsuka

    Billy Killian never made it out of the minor leagues, but the other five players in this trade had respectable major league careers. However, the key word there is respectable.

    Adrian Gonzalez became a superstar while playing for the San Diego Padres. Even though he had to play in a very pitcher-friendly ballpark, he still put up around 30 home runs and 100 RBI consistently.

    Gonzalez has since moved on to Boston, but the San Diego Padres pulled off an excellent trade to get him when he was still a young prospect.

19. Aramis Ramirez Comes to Wrigleyville (2003)

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    Chicago Cubs receive Aramis Ramirez, Kenny Lofton and cash

    Pittsburgh Pirates receive Bobby Hill, Jose Hernandez and Matt Bruback

    The only real prize in this trade turned out to be Aramis Ramirez. He developed into a very consistent force in the middle of the Chicago lineup and has averaged 30 home runs and 108 RBI per 162 games in his career.

    The Pittsburgh Pirates are definitely better than they were when Ramirez was shipped away, but if they still had him at the hot corner, they could be that much better.

18. Randy Johnson Is Sent to Seattle (1989)

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    Seattle Mariners receive Randy Johnson, Gene Harris and Brian Holman

    Montreal Expos receive Mark Langston and Mike Campbell

    Randy Johnson was just beginning his career and was actually 0-4 at the beginning in 1989. The Montreal Expos sent him to Seattle, and the rest speaks for itself. Johnson became one of the best strikeout pitchers in baseball history and won 303 games.

    Mark Langston, on the other hand, pitched very well for the Montreal Expos, but after that very good 12-9 performance, he was off to the California Angels while the Mariners were still holding on to Johnson, who was only getting better.

17. Jamie Moyer Revitalizes His Career as a 33-Year-Old in Seattle (1996)

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    Seattle Mariners receive Jamie Moyer

    Boston Red Sox receive Darren Bragg

    Darren Bragg was an average player for the Boston Red Sox but never really reached base enough to become a huge threat.

    Jamie Moyer was finally able to find success in Seattle and ended up winning 145 games in 11 seasons. For a pitcher who wasn't able to stick with a franchise throughout his prime, that is pretty impressive.

    At the time, this trade probably didn't seem that bad because Moyer was probably on his way over the hill. In hindsight, it is rather obvious that his impact is still being felt today.

16. David Cone Becomes Part of the Yankee Dynasty (1995)

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    New York Yankees receive David Cone

    Toronto Blue Jays receive Jason Jarvis, Mike Gordon and Marty Janzen

    David Cone won four World Series rings while playing for the New York Yankees and won 20 games in 1998. Of the three players he was traded for, only Janzen appeared in the major leagues during parts of two different seasons for the Toronto Blue Jays.

    Trading for prospects is always dangerous, but here is one time where it really did not pay off.

15. Tim Hudson Is Part of the Oakland Pitcher Sale (2004)

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    Atlanta Braves receive Tim Hudson

    Oakland Athletics receive Juan Cruz, Dan Meyer and Charles Thomas

    Tim Hudson came to Atlanta as a 29-year-old and has won at least 10 games every season except 2009, when he missed substantial time.

    Juan Cruz is still a very good pitcher with the Pittsburgh Pirates, but Dan Meyer never lived up to the potential that made him an important part of this trade. Oakland was selling its top pitchers, so that wasn't the problem. The problem was that it could have gotten much more in return.

14. Bartolo Colon Is Swapped for a Bevy of Prospects (2002)

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    Montreal Expos receive Bartolo Colon and Tim Drew

    Cleveland Indians receive Cliff Lee, Brandon Phillips, Grady Sizemore and Lee Stevens

    Granted, Bartolo Colon was one of the better pitchers in baseball at the time of this trade. In that sense, he should have had a high price tag.

    However, who would have thought that one of the better pitchers and one of the better second basemen in baseball today would be going the other way?

    At the time, this deal probably made sense, but in hindsight these four players have done a lot more than win 10 games like Colon did for the Montreal Expos before he found a new home in 2003.

13. Jose Bautista for a Player to Be Named Later (2008)

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    Toronto Blue Jays receive Jose Bautista

    Pittsburgh Pirates receive Robinzon Diaz as a player to be named later

    In 2008, Jose Bautista had not hit more than 16 home runs in any one regular season. Little did the Pittsburgh Pirates know that he would hit 54 home runs in 2010 and 43 more in 2011.

    Robinzon Diaz only appeared in 43 games as a member of the Pittsburgh Pirates and was out of Major League Baseball after the 2009 season.

    Bautista made a very quick ascension to stardom, and the Pittsburgh Pirates must regret letting him slip away at such a low price.

12. Bobby Abreu Is Traded to Philadelphia (1997)

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    Philadelphia Phillies receive Bobby Abreu

    Tampa Bay Devil Rays receive Kevin Stocker

    Many of you might realize that I am a Philadelphia Phillies fan. When Bobby Abreu still played for the Philadelphia Phillies and I would watch the games with announcers from another team, this trade was mentioned almost every game.

    Stocker was a serviceable shortstop, but Abreu became one of the better all-around outfielders in baseball. Right out of the blocks, the Tampa Bay Devil Rays stumbled on the trade market.

11. The Yankees Ship Jay Buhner to the Pacific Northwest (1988)

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    Seattle Mariners receive Jay Buhner, Rich Balabon and Troy Evers

    New York Yankees receive Ken Phelps

    At the time, this trade probably seemed like a good deal. Ken Phelps had hit 27 home runs in the 1987 season and eventually hit 24 in 1988. All the Yankees needed to sacrifice was a young Jay Buhner and two other players who we now know never made it out of the minor leagues.

    It wouldn't have been a bad trade except for the fact that Buhner ended up hitting 307 home runs in a Seattle Mariners uniform and Phelps was out of baseball within a few years. This was not exactly a shining moment in Yankees history.

10. There Is No Room for Brandon Phillips in Cleveland (2006)

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    Cincinnati Reds receive Brandon Phillips

    Cleveland Indians receive Jeff Stevens

    Jeff Stevens never played a game in a Cleveland Indians uniform. Brandon Phillips became one of the best second basemen in the game who provides both power and speed in the middle of the lineup.

    Phillips seems to have a penchant for being traded in lopsided deals. However, if he ever leaves Cincinnati, he definitely deserves to finally get traded for fair market value.

9. Pedro Martinez Moves North of the Border (1993)

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    Montreal Expos receive Pedro Martinez

    Los Angeles Dodgers receive Delino DeShields

    The Dodgers have fostered some of the best pitchers in baseball history. Sandy Koufax, Don Drysdale and of course Pedro Martinez all began within the organization. The problem with Martinez was that they traded him away before he really began to dominate.

    Delino DeShields was not a bad player, but I had no choice but to rate this as one of the worst trades in the past 25 years. The Dodgers traded away a player who would win three Cy Young awards. That's kind of tough to take.

8. Curt Schilling Moves to the Desert (2000)

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    Arizona Diamondbacks receive Curt Schilling

    Philadelphia Phillies receive Travis Lee, Omar Daal, Nelson Figueroa and Vicente Padilla

    Curt Schilling joined the Arizona Diamondbacks and paired with Randy Johnson to capture a World Series ring. He went on to have even more success as a member of the Boston Red Sox.

    The Philadelphia Phillies received very little production out of any of these players except Vicente Padilla. See the imbalance here?

7. John Smoltz Becomes a Brave (1987)

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    Atlanta Braves receive John Smoltz

    Detroit Tigers receive Doyle Alexander

    This is pushing 25 years, but we are still within the time limits. John Smoltz developed into one of the best starting pitchers in baseball before he hurt himself and came back as one of the best closers in baseball before joining the starting rotation once again.

    Alexander pitched very well for Detroit in 1987 and 1988, but he led the league in losses with 18 in 1989 before he retired. This pairing ended up a little bit lopsided.

6. Nelson Cruz Was Less Valuable Than Keith Ginter? (2004)

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    Milwaukee Brewers receive Nelson Cruz and Justin Lehr

    Oakland Athletics receive Keith Ginter

    Keith Ginter played one season with the Oakland Athletics and hit .161. He hasn't been in the major leagues since.

    In his defense, though, he did have two good seasons with the Milwaukee Brewers before they traded him, so I can kind of understand why Oakland made this trade.

    However, looking back at this trade, Nelson Cruz has since moved to Texas and developed a huge power bat. Had it known this was coming, Oakland surely would have wanted to keep him around.

5. Jeff Bagwell Heads to Houston (1990)

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    Houston Astros receive Jeff Bagwell

    Boston Red Sox receive Larry Andersen

    This one has gone down as one of the worst trades in all of baseball history.

    Larry Andersen did a fine job (1.23 ERA) for the portion of 1990 that he was with the Boston Red Sox, but the 15 games he appeared in were probably not worth the Hall of Fame-worthy career that Bagwell ended up putting together.

4. Fred McGriff Anchors the Atlanta Lineup (1993)

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    Atlanta Braves receive Fred McGriff

    San Diego Padres receive Vince Moore, Donnie Elliott and Melvin Nieves

    Fred McGriff made three consecutive All-Star appearances as a member of the Atlanta Braves and drove in over 90 runs in each of his four full seasons with the team.

    On the other hand, Vince Moore never made it to the major leagues, Donnie Elliott played in just over one season and Melvin Nieves hit over 20 home runs two separate times during his career but was plagued by a propensity for striking out.

    McGriff was not with the Atlanta Braves very long, but he had a large impact and was a steal on the trade market.

3. Jason Varitek and Derek Lowe Become Boston Institutions (1997)

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    Boston Red Sox receive Jason Varitek and Derek Lowe

    Seattle Mariners receive Heathcliff Slocumb

    Jason Varitek and Derek Lowe both enjoyed great careers in Boston. Varitek helped break the Curse of the Bambino from behind the plate while Lowe was having a good season on the mound.

    Heathcliff Slocumb, on the other hand, didn't enjoy quite so much success with Seattle and was never able to regain the success he had in Boston or with the Philadelphia Phillies before that.

2. Sammy Sosa Moves Across the Windy City (1992)

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    Chicago Cubs receive Sammy Sosa and Ken Patterson

    Chicago White Sox receive George Bell

    If the Chicago White Sox would have known that Sammy Sosa was going to become one of the best home run hitters of the late '90s, there is no way they would have made this trade.

    However, Sosa was still a prospect at this point, and Bell was an established outfield presence. At the time, this trade might have made sense, but in hindsight it was a major blunder for the White Sox.

1. Mark McGwire Starts Crushing in St. Louis (1997)

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    St. Louis Cardinals receive Mark McGwire

    Oakland Athletics receive Blake Stein, T.J. Mathews and Eric Ludwick

    McGwire had hit 52 home runs in 1996, and he ended up hitting 58 home runs in 1997. In the midst of that campaign, he was traded for three prospects who never panned out.

    McGwire hit 70 home runs in 1998 to shatter Roger Maris' single-season home run record, and those three prospects turned out to be busts. This has to be one of the most lopsided trades in Major League Baseball history.

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