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The Most Disappointing Free Agents in MLB History

By (Featured Columnist) on September 26, 2011

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BOSTON, MA - SEPTEMBER 17:  Carl Crawford #13 of the Boston Red Sox is safe at home as Jose Lobaton #31 of the Tampa Bay Rays applies a late tag in the third inning at Fenway Park September 17, 2011 in Boston, Massachusetts. (Photo by Jim Rogash/Getty Ima
Jim Rogash/Getty Images

Carl Crawford has had a difficult year to say the least. He just came out to TBO and said that he would be "devastated" if the Tampa Bay Rays pass the Boston Red Sox for the Wild Card. He also went on to say that even if this season has been disappointing, he will be back and will do better.

After signing such a big contract in the offseason, Crawford has been very disappointing this season. However, this isn't the first time something like that happen. There have been bad free-agent contracts throughout the history of baseball.

Let's take a look at five of the most disappointing free agents in MLB history.

Carl Crawford Signing with the Boston Red Sox

BOSTON, MA - SEPTEMBER 14: Carl Crawford #13 of the Boston Red Sox swings at a pitch in the ninth inning against the Toronto Blue Jays at Fenway Park on September 14, 2011 in Boston, Massachusetts. The Blue Jays won the game 5-4. (Photo by Darren McColles
Darren McCollester/Getty Images

I am a huge Carl Crawford fan in general. However, this has been a very difficult season for him so far. He is only batting .258 with 11 home runs, 56 RBI and a .293 on-base percentage.

While this might not be that bad of a year for quite a few players, a free agent who signed a seven-year, $142 million contract this past winter is expected to do quite a bit more.

Crawford is a great player, and he still has a lot of time left on his contract. Maybe he will be able to work his way off of the list if he starts performing at the level that I know he can perform at.

Greg Vaughn Signing with the Tampa Bay Devil Rays

ST. PETERSBURG, FL- FEBRUARY 22:  Greg Vaughn #23 poses for a portrait during the Tampa Bay Devil Rays Media Day at Florida Power Park on February 22, 2003 in St. Petersburg, Florida. (Photo by: Ezra Shaw/Getty Images)
Ezra Shaw/Getty Images

I remember thinking about the home run race in 1998 and thinking that Greg Vaughn got ripped off. He hit 50 home runs that season which would normally be celebrated, but he got much less attention because that season 50 home runs only got him fourth place on the Major League Baseball home run tally. He followed that up with 45 home runs the next season.

This outburst of power earned him a four-year, $34 million contract with the Tampa Bay Devil Rays. His power production dropped off, and his batting average was much less than desirable. He did not develop into the power-hitting centerpiece that I am sure the Devil Rays were looking for.

Chan Ho Park Signing with the Texas Rangers

ANAHEIM, CA - JUNE 22:  Pitcher Chan Ho Park #61 of the Texas Rangers looks on from the dugout during the game against the Los Angeles Angels of Anaheim on June 22, 2005 at Angel Stadium in Anaheim, California.  (Photo by Lisa Blumenfeld/Getty Images)
Lisa Blumenfeld/Getty Images

In 2001, Chan Ho Park signed a five-year, $65 million contract with the Texas Rangers. He had been solid with the Los Angeles Dodgers before the time. However, the move to Texas was not quite as successful as his previous tenure had been.

He had particular problems pitching at home with a 6.75 ERA over the term of his contract. This is obviously a problem when approximately half of the pitcher's starts will be at home. This is a big price to pay for a performance that was not well received in Texas.

Andruw Jones Signing with the Los Angeles Dodgers

LOS ANGELES, CA - JULY 12:  Andruw Jones #25 of the Los Angeles Dodgers bats against the Florida Marlins on July 12, 2008 at Dodger Stadiium in Los Angeles, California. The Marlins won 5-3 in 11 innings.  (Photo by Stephen Dunn/Getty Images)
Stephen Dunn/Getty Images

I grew up watching a lot of Atlanta Braves baseball, so I knew that Andruw Jones could crush the ball (51 home runs in 2005). However, once he signed that two-year, $36.2 million contract with the Los Angeles Dodgers, life was not quite the same for him.

In his first season in Los Angeles, he only hit .158 with three home runs in 75 games. He restructured his contract at the end of the season, and his career has gotten better since that season. However, at the time of the contract, Los Angeles was pretty disappointed in his performance.

Jason Schmidt Signing with the Los Angeles Dodgers

LOS ANGELES, CA - JUNE 16:  Jason Schmidt #29 of the Los Angeles Dodgers throws a pitch in the first inning against the Los Angeles Angels of Anaheim during an interleague game at Dodger Stadium on June 16, 2007 in Los Angeles, California. The Angels defe
Jeff Gross/Getty Images

He had a great run going in San Francisco where he won 17 games in 2003 and 18 games in 2004. The next two seasons were not quite that high on the wins column, but he had done enough to be signed by the Dodgers to a three-year, $47 million contract in 2006.

The problem with that contract is that it quite simply didn't work out. In 2007, he only started six games and went 1-4 with a 6.31 ERA. He did not pitch in the major leagues in 2008, but he returned in 2009 to start four games with a record of 2-2 and a 5.60 ERA.

Not quite an ideal return on that investment.

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