MLB

Adrian Gonzalez and the 10 Largest Contract Extensions in MLB History

Nick StewartContributor IApril 22, 2011

Adrian Gonzalez and the 10 Largest Contract Extensions in MLB History

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    BOSTON, MA - APRIL 16, 2011:  Adrian Gonzalez #28 of the Boston Red Sox reacts against the Toronto Blue Jays at Fenway Park April 16, 2011 in Boston, Massachusetts. (Photo by Jim Rogash/Getty Images)
    Jim Rogash/Getty Images

    Grin away, Adrian Gonzalez. I would be grinning too if I was making your money.

    Adrian Gonzalez just milked the Boston Red Sox for a whopping $154M for a six-year deal. I, for one, can't imagine paying that kind of money for one player. Then again, I'm not trying to beat the New York Yankees year in and year out.

    The Yankees and the Red Sox certainly don't mind spending the money. However, other teams have made lucrative deals to keep star players on their payrolls as well.

    The following are the 10 most expensive contract extensions in MLB history.

No. 10: Ken Griffey Jr., CIN

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    SEATTLE - MAY 31:  Ken Griffey Jr. #24 of the Seattle Mariners bats against the Minnesota Twins at Safeco Field on May 31, 2010 in Seattle, Washington. (Photo by Otto Greule Jr/Getty Images)
    Otto Greule Jr/Getty Images

    In 2000, the Cincinnati Reds made an eight-year deal to retain superstar Ken Griffey Jr., one of the greatest five-tool players to ever play baseball. How much would it cost to keep Griffey in Ohio?

    $116.5M over eight years.

No. 9: Ryan Howard, PHI

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    WASHINGTON, DC - APRIL 12: Carlos Ruiz #51 of the Philadelphia Phillies and teammates Ryan Howard #6 and Wilson Valdez #21 during a pitching change against the Washington Nationals at Nationals Park on April 12, 2011 in Washington, DC. (Photo by Rob Carr/
    Rob Carr/Getty Images

    Ever notice how much these guys smile, even when they are losing?

    Ryan Howard hasn't got many reasons not to smile, though. He is on one of the best teams in baseball and has one of the fattest checks in baseball as well.

    Howard signed a five-year extension for $125M.

No. 8: Vernon Wells, TOR

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    ANAHEIM, CA - APRIL 08:  Vernon Wells #10 of the Los Angeles Angels of Anaheim bats against the Toronto Blue Jays at Angel Stadium of Anaheim on April 8, 2011 in Anaheim, California.  (Photo by Jeff Gross/Getty Images)
    Jeff Gross/Getty Images

    In 2008, the Toronto Blue Jays gave Vernon Wells a six-year contract extension for $126M. Vernon apparently ended up not being worth the money to the Jays, who traded him to the Angels.

    Maybe the money was in Canadian funds.

No. 7: Johan Santana, NYM

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    PORT ST. LUCIE, FL - FEBRUARY 24:  Johan Santana #57 of the New York Mets poses for a portrait during the New York Mets Photo Day on February 24, 2011 at Digital Domain Park in Port St. Lucie, Florida.  (Photo by Elsa/Getty Images)
    Elsa/Getty Images

    Johan Santana signed a six-year contract extension for $137.5M.

    He has also been hurt every year for three years straight.

    Wow. If I call in sick to work, they fire me. This guy gets a raise? I'm not saying I can hit his change-up (which is unbelievable), but I do show up to work every day!

    Where's my contract extension?!

No. 6: Todd Helton, COL

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    DENVER, CO - APRIL 06:  First baseman Todd Helton #17 of the Colorado Rockies plays defense against the Los Angeles Dodgers at Coors Field on April 6, 2011 in Denver, Colorado.  (Photo by Doug Pensinger/Getty Images)
    Doug Pensinger/Getty Images

    Why so angry, Todd?

    You got an eight-year deal with the Rockies for $141.5M!

    Not bad for a guy with a degenerative back condition. 

    To be fair, Helton is probably one of the most underrated players in MLB. He has always displayed hitting prowess and a Gold Glove or two, or three, to match.

No. 5: Miguel Cabrera, DET

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    OAKLAND, CA - APRIL 17:  Miguel Cabrera #24 of the Detroit Tigers walks out to the field for their game against the Oakland Athletics at Oakland-Alameda County Coliseum on April 17, 2011 in Oakland, California.  (Photo by Ezra Shaw/Getty Images)
    Ezra Shaw/Getty Images

    In 2008, Detroit gave Miguel Cabrera a seven-year contract extension for a whopping $152.3M.

    I wonder how they come up with these numbers.

    Miguel is definitely a good ballplayer but may be the single reason Detroit is in such a rough depression.

No. 4: Adrian Gonzalez, BOS

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    BOSTON, MA - APRIL 10:  Adrian Gonzalez #28 of the Boston Red Sox reacts after being hit by a pitch against the New York Yankees at Fenway Park April 10, 2011 in Boston, Massachusetts. (Photo by Jim Rogash/Getty Images)
    Jim Rogash/Getty Images

    Adrian Gonzalez signed a seven-year deal for $154M.

    And the Sox are in last place in the AL East.

    Gonzalez costs nearly as much, per year, as the entire Rays franchise.

    He is, however, a bright spot on a team that is proving that you don't always get what you pay for all the time!

No. 3: Troy Tulowitzki, COL

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    DENVER - APRIL 03:  Troy Tulowitski #2 of the Colorado Rockies gets the force on Scott Hairston #9 of the Arizona Diamondbacks at second and completes the double play as he throw to get Chad Tracey at first in the eighth inning as the Rockies defeated the
    Doug Pensinger/Getty Images

    Troy Tulowitzki is the best shortstop in the major leagues. He makes plays that no human being should be able to make. He has fantastic range and fielding ability and makes great plays with absolutely no regard for himself.

    Until contract time. Tulowitzki can field like Ozzie Smith but actually has a bat as well. I think he carries it into the negotiation room with him.

    The Rockies gave Tulo an eight-year extension for $157.75M.

No. 2: Joe Mauer, MIN

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    MINNEAPOLIS, MN - APRIL 9: Joe Mauer #7 of the Minnesota Twins in the dugout during the seventh inning of their game against the Oakland Athletics on April 9, 2011 at Target Field in Minneapolis, Minnesota. Athletics defeated the Twins 1-0. (Photo by Hann
    Hannah Foslien/Getty Images

    Three batting titles plus three Gold Gloves = HUGE contract extension.

    Joe Mauer is the most sought-after player in the bigs. His combination of power and defense makes him one of those catchers that will be in the Hall of Fame at the end of his career.

    If the Twins have their way, he will enter the Hall in a Minnesota uniform.

    Mauer signed an eight-year, $184M contract with the Twins in 2011, putting him at No. 2 on the list of fattest contract extensions.

    Is he worth it? Maybe. We will find out in 2018.

No. 1: Derek Jeter, NYY

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    NEW YORK, NY - APRIL 16:  Derek Jeter #2 of the New York Yankees fields the ball against the Texas Rangers on April 16, 2011 at Yankee Stadium in the Bronx borough of New York City. The Yankees defeated the Rangers 5-2.  (Photo by Jim McIsaac/Getty Images
    Jim McIsaac/Getty Images

    Derek Jeter is not the highest-paid player in baseball, but he did have the largest contract extension in history.

    In 2001, Jeter signed a nine-year deal with the Yankees for $189M.

    The Yankees made sure their franchise face wasn't going anywhere. Was he worth it? To the Yankees, yes. To a smaller ball club, probably not.

    The Yankees have had only one world championship in that time frame. The Marlins have had only one as well, and they would have had to get corporate sponsorship from Microsoft to get Jeter in Florida.

    The point is this: Yes, these players are great. They really are the best of the best. I am uncertain whether they are so good that they deserve to be paid the GNP of a small country, though. 

    They are all on good teams, but teams are determined by championships, and none of them has contributed solely to winning one.

    I may just be jealous, though. I have decided, at my job, that they pay me just enough not to quit, so I work just hard enough not to get fired. Maybe my bosses should buy a team.

    Maybe the Dodgers are on the market...

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