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ANAHEIM, CA - JULY 13:  National League All-Star Albert Pujols #5 of the St. Louis Cardinals looks on during the 81st MLB All-Star Game at Angel Stadium of Anaheim on July 13, 2010 in Anaheim, California.  (Photo by Lisa Blumenfeld/Getty Images)
ANAHEIM, CA - JULY 13: National League All-Star Albert Pujols #5 of the St. Louis Cardinals looks on during the 81st MLB All-Star Game at Angel Stadium of Anaheim on July 13, 2010 in Anaheim, California. (Photo by Lisa Blumenfeld/Getty Images)Lisa Blumenfeld/Getty Images

Troy Tulowitzki, Albert Pujols and The 10 Biggest Contract Extensions In History

Patrick ClarkeDec 14, 2010

In the spirit of the massive multi-million dollar contracts MLB teams are handing out this offseason, let's take a look at the 10 largest contract extensions in history.

Just a heads-up: the list includes a couple of enormous Yankee contracts. But above all else, the names are notable, the numbers are jaw-dropping and the extensions are legendary.

No. 10: Matt Holliday

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ATLANTA - SEPTEMBER 09:  Matt Holliday #7 of the St. Louis Cardinals against the Atlanta Braves at Turner Field on September 9, 2010 in Atlanta, Georgia.  (Photo by Kevin C. Cox/Getty Images)
ATLANTA - SEPTEMBER 09: Matt Holliday #7 of the St. Louis Cardinals against the Atlanta Braves at Turner Field on September 9, 2010 in Atlanta, Georgia. (Photo by Kevin C. Cox/Getty Images)

In 2010 the St. Louis Cardinals outfielder signed an extension to remain with the team 2016. The deal is currently worth seven years and $120 million.

No. 9: Ryan Howard

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PHILADELPHIA - OCTOBER 23:  Ryan Howard #6 of the Philadelphia Phillies reacts after striking out against the San Francisco Giants in Game Six of the NLCS during the 2010 MLB Playoffs at Citizens Bank Park on October 23, 2010 in Philadelphia, Pennsylvania
PHILADELPHIA - OCTOBER 23: Ryan Howard #6 of the Philadelphia Phillies reacts after striking out against the San Francisco Giants in Game Six of the NLCS during the 2010 MLB Playoffs at Citizens Bank Park on October 23, 2010 in Philadelphia, Pennsylvania

Philadelphia's Ryan Howard signed a contract extension with the Phillies in 2010 that will keep him in red pinstripes until at least 2017. The contract is for five years and an estimated $125 million.

No. 8: Johan Santana

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NEW YORK - AUGUST 28:  Johan Santana #57 of the New York Mets delivers a pitch against the Houston Astros on August 28, 2010 at Citi Field in the Flushing neighborhood of the Queens borough of New York City.  (Photo by Jim McIsaac/Getty Images)
NEW YORK - AUGUST 28: Johan Santana #57 of the New York Mets delivers a pitch against the Houston Astros on August 28, 2010 at Citi Field in the Flushing neighborhood of the Queens borough of New York City. (Photo by Jim McIsaac/Getty Images)

Johan Santana was traded to the New York Mets during the 2007-2008 offseason and signed an extension with the team in 2008 worth six years and $137.5 million.

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No. 7: Todd Helton

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ST. LOUIS - OCTOBER 2: Todd Helton #17 of the Colorado Rockies mis plays a ground ball against the St. Louis Cardinals at Busch Stadium on October 2, 2010 in St. Louis, Missouri.  The Cardinals beat the Rockies 1-0 in 11 innings.  (Photo by Dilip Vishwana
ST. LOUIS - OCTOBER 2: Todd Helton #17 of the Colorado Rockies mis plays a ground ball against the St. Louis Cardinals at Busch Stadium on October 2, 2010 in St. Louis, Missouri. The Cardinals beat the Rockies 1-0 in 11 innings. (Photo by Dilip Vishwana

The Rockies first baseman signed an extension way back in 2001. The deal was for nine years and $141.5 million. It was the largest in Colorado Rockies at the time.

No. 6: Miguel Cabrera

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NEW YORK - AUGUST 19:  Miguel Cabrera #24 of the Detroit Tigers runs the bases after his first inning two run home run against the New York Yankees on August 19, 2010 at Yankee Stadium in the Bronx borough of New York City.  (Photo by Jim McIsaac/Getty Im
NEW YORK - AUGUST 19: Miguel Cabrera #24 of the Detroit Tigers runs the bases after his first inning two run home run against the New York Yankees on August 19, 2010 at Yankee Stadium in the Bronx borough of New York City. (Photo by Jim McIsaac/Getty Im

The Detroit Tigers first baseman signed a monster extension in 2008 to remain with the team through 2015. The deal was for eight years and $153 million.

No. 5: Troy Tulowitzki

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DENVER - SEPTEMBER 25:  Troy Tulowitzki #2 of the Colorado Rockies hits a two run homerun to give the Rockies a 5-4 lead over the San Francisco Giants in the fifth inning at Coors Field on September 25, 2010 in Denver, Colorado.  (Photo by Doug Pensinger/
DENVER - SEPTEMBER 25: Troy Tulowitzki #2 of the Colorado Rockies hits a two run homerun to give the Rockies a 5-4 lead over the San Francisco Giants in the fifth inning at Coors Field on September 25, 2010 in Denver, Colorado. (Photo by Doug Pensinger/

The shortstop was rewarded for a spectacular season in 2010 with a humongous extension in the offseason for 10 years and worth close to $158 million.

The deal surpassed Todd Helton's for the largest in Rockies history.

No. 4: Joe Mauer

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NEW YORK - OCTOBER 09:  Joe Mauer #7 of the Minnesota Twins looks on during batting practice against the New York Yankees during Game Three of the ALDS part of the 2010 MLB Playoffs at Yankee Stadium on October 9, 2010 in the Bronx borough of New York Cit
NEW YORK - OCTOBER 09: Joe Mauer #7 of the Minnesota Twins looks on during batting practice against the New York Yankees during Game Three of the ALDS part of the 2010 MLB Playoffs at Yankee Stadium on October 9, 2010 in the Bronx borough of New York Cit

The Twins MVP-caliber catcher signed one of baseball's largest contract extensions in 2010. The deal has Mauer in Minnesota until 2018, covering eight seasons and paying him an estimated $184 million.

No. 3: Derek Jeter

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TAMPA, FL - DECEMBER 07:   Shortstop Derek Jeter of the New York Yankees talks to the media during a press conference to announce his new contract with the club on December 7, 2010 in Tampa, Florida.  (Photo by Tim Boyles/Getty Images)
TAMPA, FL - DECEMBER 07: Shortstop Derek Jeter of the New York Yankees talks to the media during a press conference to announce his new contract with the club on December 7, 2010 in Tampa, Florida. (Photo by Tim Boyles/Getty Images)

Derek Jeter's extension with the New York Yankees back in 2001 was a truly eye-popping deal. The extension would keep Jeter in the big apple for 10 seasons and pay him $189 million for his troubles.

No. 2: Albert Pujols

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ATLANTA - SEPTEMBER 09:  Albert Pujols #5 of the St. Louis Cardinals against the Atlanta Braves at Turner Field on September 9, 2010 in Atlanta, Georgia.  (Photo by Kevin C. Cox/Getty Images)
ATLANTA - SEPTEMBER 09: Albert Pujols #5 of the St. Louis Cardinals against the Atlanta Braves at Turner Field on September 9, 2010 in Atlanta, Georgia. (Photo by Kevin C. Cox/Getty Images)

No. 2 is a little bit imaginative. Pujols and the Cardinals are expecting an extension very soon, but it hasn't happened yet. So we will base Pujols' extension on what experts are predicting for the stud first baseman.

According to Paul White of USA Today, the predictions average out somewhere in the ballpark of eight years and $210 million, putting him second on the all-time list.

No. 1: Alex Rodriguez

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ARLINGTON, TX - OCTOBER 22:  Alex Rodriguez #13 of the New York Yankees looks on during batting practice against the Texas Rangers in Game Six of the ALCS during the 2010 MLB Playoffs at Rangers Ballpark in Arlington on October 22, 2010 in Arlington, Texa
ARLINGTON, TX - OCTOBER 22: Alex Rodriguez #13 of the New York Yankees looks on during batting practice against the Texas Rangers in Game Six of the ALCS during the 2010 MLB Playoffs at Rangers Ballpark in Arlington on October 22, 2010 in Arlington, Texa

No surprise here. A-Rod's 2008 extension with the New York Yankees is the largest contract extension in sports history, let alone Major League Baseball.

Rodriguez signed a 10-year deal worth an incredible $275 million. The deal keeps A-Rod in New York through 2017 and makes him a very wealth man.

Patrick Clarke is a student at Towson University and a writing intern for Bleacher Report.

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