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Private Investor Group

Standard Investment Plays

Top 5 Worst MLB Trade Deadline Moves

As the 2012 Major League baseball trade deadline approaches, we thought it might be time to take a look at, and compile a list of the top five worst deadline deals made over the past 25 years.

While great trades are ones that you notice right away--like when the Philadelphia Phillies managed to package several top prospects and land pitching ace Roy Halladay from theToronto Blue Jays, or when the St. Louis Cardinals picked up Mark McGwire from the Oakland A's in 1997. We all seem to forget the worst deals ever made. Unless of course our team was on the wrong end of it.

But what makes a trade bad?

Well for starters, when a team gives up a future Hall of Famer or a player that went on to greatness with their new team, while it got basically nothing in return.

And while it can sometimes can take months, even years to see just how bad these deals really were--especially if there were young underachieving players involved--eventually they surface as some of baseball's biggest gaffes.

While, there have been plenty of trade deadline disasters since the league began in 1869, the following five, in no specific order, find a special place on our list.

5. Randy Johnson for Mark Langston(1989)--Sure, the Montreal Expos were in the hunt for the division title when they made this move, but it would eventually prove to be a huge blunder when they gave up one of the most dominant pitchers in baseball history, along with Gene Harris and Brian Holman, to the Seattle Mariners for Mark Langston. Although Langston finished the 1989 season, 12-9 with a 2.39 ERA, he would leave Montreal at in December of that year as a free agent. Johnson? Well you know that part.

4. David Cone for Marty Janzen(1995)--Maybe Canadians should stick to hockey, because the Toronto Blue Jays committed what is probably the worst trade in franchise history when they dealt David Cone to the New York Yankees for Jason Jarvis, Mike Gordon and Marty Janzen. Cone went 9-2 down the stretch, helping the Yankees reach the postseason for the first time since 1981, before eventually winning four World Series championships with New York, and even threw a perfect game. Yup, and you guessed it--only Janzen made it to the major league level. And to boot, he stepped onto the field just a total of 27 games spread over two major league seasons.

3. Jason Schmidt for Armando Rios (2001)--This just one of the many reasons the Pirates are ona 19-year losing season streak, but no doubt one of the bigger bungles. So what exactly did Pittsburgh get from trading Jason Schmidt and John Vander Wal to the San Francisco Giants for Armando Rios and Ryan Vogelsong? Well, nothing. Rios would play for just two seasons for the Pirates before being released, and Vogelsong would play for unproductive five. On the other hand, Schmidt would go on to finish second and fourth in CY Young voting in 2003 and 2004, respectively, and make the All-Star team three times. He would also end up 78-37 with an ERA of 3.36 in 1,069 innings pitched for the Giants.

2. Curt Schilling for Mike Boddicker(1988)-Who knows exactly what the Boston Red Sox where thinking when they traded then minor leaguer Curt Schilling, and a rookie named Brady Anderson to the Baltimore Orioles for starting pitcher Mike Boddicker. Boddicker played 2-1/2 seasons with the Sox, going 39-22 with an ERA of 3.49, while Anderson would prove to be a more than capable outfielder for the Orioles for 14 seasons. And Schilling? Well, he would go on to lead the Arizona Diamondbacks to the World Series title in 2001, before Boston regained consciousness and brought him back to bean town to do the same in 2004.


1. A.J. Pierzynski for Francisco Liriano (2003) --While it may look like the Twins came up big with this one, dealing veteran catcher A.J. Pierzynski, who hit .272/.319/.410 in his one season in San Francisco, for three future major leaguers. The Twins were the eventual losers in this one. Sure, Liriano was an All-Star in his rookie season, and Joe Nathan became the Twins closer and saved 247 games over six seasons. But Boof Bonser was a bust. Meanwhile, Pierzynski went on to become a two-time all star and a World Series Champion with the Chicago White Sox in 2005.  And today, after eight seasons in Chi town, is still batting nearly .300 with 16 home runs midway through the 2012 season.

Plus 1 Coopers Pick