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SAN FRANCISCO - OCTOBER 27:  Barry Zito of the San Francisco Giants looks on against the Texas Rangers in Game One of the 2010 MLB World Series at AT&T Park on October 27, 2010 in San Francisco, California.  (Photo by Jed Jacobsohn/Getty Images)
SAN FRANCISCO - OCTOBER 27: Barry Zito of the San Francisco Giants looks on against the Texas Rangers in Game One of the 2010 MLB World Series at AT&T Park on October 27, 2010 in San Francisco, California. (Photo by Jed Jacobsohn/Getty Images)Jed Jacobsohn/Getty Images

MLB Free Agency: The 10 Worst Contracts Ever Handed Out To Big League Pitchers

Chris LeydenJun 7, 2018

In a sport where a lot of the contracts seem absolutely ridiculous, this list includes the ten worst contracts handed out to MLB pitchers.

The interesting part of this list is that although sometimes the deal looks idiotic right away, other times it takes a few years to prove just how much of a waste of money a player is.

This list is entirely focused on relatively recent contract signings, because these contracts are so much bigger and look so much worse than any contracts in the past.

If you want to add your own pitcher or don't agree with one of my picks feel free to comment below.

#10 Oliver Perez- New York Mets

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NEW YORK - MAY 10:  Oliver Perez #46 of the New York Mets looks on from the dugout against the Washington Nationals on May 10, 2010 at Citi Field in the Flushing neighborhood of the Queens borough of New York City.  (Photo by Jim McIsaac/Getty Images)
NEW YORK - MAY 10: Oliver Perez #46 of the New York Mets looks on from the dugout against the Washington Nationals on May 10, 2010 at Citi Field in the Flushing neighborhood of the Queens borough of New York City. (Photo by Jim McIsaac/Getty Images)

In February of 2009 the New York Mets gave Oliver Perez a three year $36 million contract.

Since that time Perez has become almost impossible to use for the Mets, and the team basically refused to play him.

This contract was a head-scratcher from the start, Perez's career record was not even above .500 when the Mets inked him for three more years.

Perez had an ERA of 6.80 over the next two years of the contract, and went 3-9 in that span. Last year the Mets asked Perez to go on a rehab assignment but Perez refused.

#9 Carlos Silva- Seattle Mariners

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SEATTLE - JULY 20:  Carlos Silva #52 of the Seattle Mariners walks off the mound against the Cleveland Indians on July 20, 2008 at Safeco Field in Seattle, Washington. The Indians defeated the Mariners 6-2. (Photo by Otto Greule Jr/Getty Images)
SEATTLE - JULY 20: Carlos Silva #52 of the Seattle Mariners walks off the mound against the Cleveland Indians on July 20, 2008 at Safeco Field in Seattle, Washington. The Indians defeated the Mariners 6-2. (Photo by Otto Greule Jr/Getty Images)

In December of 2007 Carlos Silva signed a contract with the Seattle Mariners for $48 million over four years.

Silva then proved what an instant great value he was by finishing his first season with the Mariners with an ERA of 6.46. To put some salt on the wound, he then only was able to pitch 30 innings the next year before being shut down with a shoulder injury.

The Mariners managed to trade Silva to the Cubs in 2009, and since then he has actually done pretty well starting that season 8-0.

#8 Denny Neagle- Colorado Rockies

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DENVER - JUNE 17:  Starting pitcher Denny Neagle #15 of the Colorado Rockies watches the game from the dugout in the bottom half of the first inning of the game against the San Diego Padres at Coors Field on June 17, 2003 in Denver, Colorado.  The Padres
DENVER - JUNE 17: Starting pitcher Denny Neagle #15 of the Colorado Rockies watches the game from the dugout in the bottom half of the first inning of the game against the San Diego Padres at Coors Field on June 17, 2003 in Denver, Colorado. The Padres

In 2000 Denny Neagle signed a five year $51 million contract with the Colorado Rockies.

Neagle was a star prior to this contract, but it seems that once he secured the big bucks he was content sitting on the bench and hanging with prostitutes.

After the contract Neagle only pitched for the first three years and was 19-23 with a 5.56 ERA. Neagle was then hurt for the fourth year.

He saved the Rockies a solid amount of money when he was caught soliciting a prostitute and the Rockies terminated his contract.

Things only got worse for Neagle who was then arrested for DUI and was mentioned in the Mitchell Report involving steroids.

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#7 Chan Ho Park- Texas Rangers

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OAKLAND , CA - JULY 14:  Chan Ho Park #61 of the Texas Rangers looks to second base after a throwing error that scored a run on a ball hit by Mark Kotsay #21 of the Oakland Athletic during an MLB game at McAfee Coliseum on July 14, 2005 in Oakland, Califo
OAKLAND , CA - JULY 14: Chan Ho Park #61 of the Texas Rangers looks to second base after a throwing error that scored a run on a ball hit by Mark Kotsay #21 of the Oakland Athletic during an MLB game at McAfee Coliseum on July 14, 2005 in Oakland, Califo

In December of 2002 the Texas Rangers gave Chan Ho Park a $65 million contract over five years.

Park had an abundance of injuries throughout the years, and when he was pitching things were not going any better.

Park went 33-33 over the span and had an ERA of 5.56. Many claim that he did so poorly because he pitched in the Rangers stadium which favored hitters, but this was not the case.

#6 Carl Pavano- New York Yankees

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MINNEAPOLIS, MN - OCTOBER 7: Carl Pavano #48 of the Minnesota Twins in the dugout in the bottom of the seventh inning during game two of the ALDS game against the New York Yankees on October 7, 2010 at Target Field in Minneapolis, Minnesota. (Photo by Han
MINNEAPOLIS, MN - OCTOBER 7: Carl Pavano #48 of the Minnesota Twins in the dugout in the bottom of the seventh inning during game two of the ALDS game against the New York Yankees on October 7, 2010 at Target Field in Minneapolis, Minnesota. (Photo by Han

Carl Pavano signed a contract with the New York Yankees in 2004 for four years and $39.95 million. He actually fired his agent after the contract for not getting $40 million but falling $50,000 short.

Pavano had a bunch of injuries and even was involved in a car accident that he didn't tell the Yankees about until two weeks later.

Over the four year contract Pavano only pitched 145 2/3 innings and had an ERA of 5.00.

#5 Kevin Brown- Los Angeles Dodgers

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8 Apr 2000: Kevin Brown #27 of the Los Angeles Dodgers shows his injured finger to Glenn Hoffman #35 and Davey Johnson during the game against the New York Mets at Shea Stadium in Flushing, New York. The Dodgers defeated the Mets 6-5. Mandatory Credit: Ez
8 Apr 2000: Kevin Brown #27 of the Los Angeles Dodgers shows his injured finger to Glenn Hoffman #35 and Davey Johnson during the game against the New York Mets at Shea Stadium in Flushing, New York. The Dodgers defeated the Mets 6-5. Mandatory Credit: Ez

In 1999 a 34-year-old Kevin Brown signed a seven year $105 million contract with the Dodgers, becoming the first player in MLB history to sign a contract over $100 million.

This seems like one of those contracts that looked doomed from the start, because Brown was already 34 and the contract would go until he was in his forties. In general pitchers do not still pitch at a very high level, or pitch at all when they are in their forties.

Brown was almost always injured over the years, and averaged only nine wins a season. He ended up having a strong year in 2003, but that may have been due to steroids because he was mentioned in the Mitchell Report.

#4 Mike Hampton- Colorado Rockies

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30 May 1998:  Mike Hampton of the Houston Astros in action during a game against the Colorado Rockies at Coors Field in Denver, Colorado. The Rockies defeated the Astros 6-3. Mandatory Credit: Brian Bahr  /Allsport
30 May 1998: Mike Hampton of the Houston Astros in action during a game against the Colorado Rockies at Coors Field in Denver, Colorado. The Rockies defeated the Astros 6-3. Mandatory Credit: Brian Bahr /Allsport

In December of 2000 Mike Hampton signed an eight year $121 million contract with the Colorado Rockies. At the time the contract was the biggest in sports history.

Hampton only played with Colorado for two years and went 21-28 over that span with a 5.75 ERA.

Hampton was then traded to the Atlanta Braves, who he also made regret taking on his contract.

#3 Barry Zito- San Francisco Giants

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SAN FRANCISCO - OCTOBER 02:  Barry Zito #75 of the San Francisco Giants wipes his head during the third inning against the San Diego Padres at AT&T Park on October 2, 2010 in San Francisco, California.  (Photo by Justin Sullivan/Getty Images)
SAN FRANCISCO - OCTOBER 02: Barry Zito #75 of the San Francisco Giants wipes his head during the third inning against the San Diego Padres at AT&T Park on October 2, 2010 in San Francisco, California. (Photo by Justin Sullivan/Getty Images)

In December of 2006 Barry Zito signed a contract with the San Francisco Giants for seven years and $126 million. This was also at the time the biggest contract ever given to a pitcher.

Zito had gone 40-57 during that contract with a 4.45 ERA.

His team, the Giants, won the World Series last year, but Zito was left off of the postseason roster.

#2 Darren Dreifort- Los Angeles Dodgers

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25 Apr 2001:  Darren Dreifort #37 of theLos Angeles Dodgers squats on the base during practice before the game against the Pittsburgh Pirates at Dodger Stadium in Los Angeles, California. The Dodgers defeated the Pirates 6-5.Mandatory Credit: Jeff Gross
25 Apr 2001: Darren Dreifort #37 of theLos Angeles Dodgers squats on the base during practice before the game against the Pittsburgh Pirates at Dodger Stadium in Los Angeles, California. The Dodgers defeated the Pirates 6-5.Mandatory Credit: Jeff Gross

In 2001 Darren Dreifort signed a five year $55 million contract with the Los Angeles Dodgers.

This move was another that looked plain stupid from the beginning because Dreifort had a career record of 39-45 before he signed the contract and also a history of arm trouble.

Dreifort ended up pitching about the amount a normal starting pitcher throws in a single year over the three years he lasted, and only had 26 starts. He managed nine wins in that span as well.

#1 Jason Schmidt- Los Angeles Dodgers

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LOS ANGELES, CA - JUNE 16:  Starting pitcher Jason Schmidt #29 of the Los Angeles Dodgers is pulled from the game in the fifth inning by manager Grady Little (R) as catcher Russell Martin (L) looks on against the Los Angeles Angels of Anaheim during an in
LOS ANGELES, CA - JUNE 16: Starting pitcher Jason Schmidt #29 of the Los Angeles Dodgers is pulled from the game in the fifth inning by manager Grady Little (R) as catcher Russell Martin (L) looks on against the Los Angeles Angels of Anaheim during an in

Unfortunately for the Dodgers they also signed Jason Schmidt to a three year $47 million contract prior to the 2007 season.

Schmidt ended up not pitching a lot, and when he did pitch it normally went very poorly. Over the length of the contract he earned $15.7 million per win, and a bit over sixty thousand per pitch thrown.

Those numbers above are just shocking, and are why Schmidt deserves to be number one on this list.

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