MLB: Troy Tulowitzki and The 15 Worst Contract Extensions in Baseball History

Andrew J. KearneyCorrespondent IIDecember 12, 2010

MLB: Troy Tulowitzki and the 15 Worst Contract Extensions in Baseball History

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    SAN FRANCISCO - OCTOBER 19:  Ryan Howard #6 of the Philadelphia Phillies stands in the batters box against the San Francisco Giants in Game Three of the NLCS during the 2010 MLB Playoffs at AT&T Park on October 19, 2010 in San Francisco, California.  (Pho
    Ezra Shaw/Getty Images

    In the dawn of baseball's "spend trend" many MLB teams have overpaid for players.  Whether it's through an extension or a free-agent signing, mistakes are made every winter.  Every year, many are left asking: "How in the hell did he get that type of deal?"  To say the least, they're often right nine times out of 10.  

    With money being thrown around more than ever in sports, MLB is the best example.  Contracts worth $100 million and up are the norm nowadays.  Without a salary cap, what can be done about this? Nothing, that's what.  Until there's a salary cap, there's no stopping excessive spending.  So, that being the case, the message to MLB franchises is simple.  SPEND AWAY!

    In today's game, if you have money you can and will win.  Though smart management plays a role, money wins titles nowadays.  Many teams, most notably the New York Yankees, have bought their way to World Series Titles.  To be honest, who can blame them.  There's nothing that states that they can't do it so it's smart business.  

    That being said, it's now time to look at some of the worst contract extensions in baseball history.  

15. Johan Santana

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    SAN FRANCISCO - JULY 18:  Johan Santana #57 of the New York Mets pitches against the San Francisco Giants at AT&T Park on July 18, 2010 in San Francisco, California.  (Photo by Ezra Shaw/Getty Images)
    Ezra Shaw/Getty Images

    The New York Mets paid a ton of money for this "money" pitcher.  He hasn't really had the chance to deliver for the 'Mazings thus far though.  In 2008, the Mets threw $137.5 million towards Santana to maintain him for just six seasons. At around $23 million per season, this steep price was a mistake.  

    Since becoming a Met, Santana has a 40-25 record with a 2.85 ERA.  Those are pretty solid numbers, but not for that type of money.  He earns over nearly $2 million per win!  WOW!  Omar Minaya made a mistake on this one.  Not to mention he sold the farm to obtain Santana's services.  Since then, they haven't been much of a threat and are rather on the decline.

14. Hideki Matsui

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    NEW YORK - APRIL 13:  Hideki Matsui #55 of the Los Angeles Angels of Anaheim acknowledges the fans after he received his World Series ring for being a member of the 2009 New York Yankees Worlder Series Championship team prior to playing against the New Yo
    Chris Trotman/Getty Images

    Aside from his 2009 World Series heroics, the Yankees didn't get repaid by Hideki Matsui as they'd hoped.  His four-year extension at around $13 million per season was far too much.  At age 32 by then, Matsui failed to live up to his contractual obligations as a Yankee.  In his first three years there (his initial contract), Matsui never missed a game.  He was often hurt during his extension years and cumulatively missed about one season.  

    While Matsui remained serviceable, he never put up those numbers like he had at the beginning of his Yankee tenure.  His fading production really plagued the Yankees who had expected great things from him.  Then again, it is the Yankees, who pay top dollar for anyone they want.  

13. Josh Beckett

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    NEW YORK - SEPTEMBER 24:  Josh Beckett #19 of the Boston Red Sox pitches against the New York Yankees on September 24, 2010 at Yankee Stadium in the Bronx borough of New York City.  (Photo by Andrew Burton/Getty Images)
    Andrew Burton/Getty Images

    If 2010 is any indication, this is one contract that is headed in a terrible direction for the Boston Red Sox. Beckett's playoff prowess is unquestioned, but he failed to deliver this past season and went just 6-6 with an ERA near 6.00.

    Beckett is one of the best "big game" pitchers of this era, which is a lot of the reason for his big contract. This alone may not be able to save him now though as Boston needs to first get back to the playoffs. While Beckett is still capable of being effective, he now needs to turn it around and prove to be the Sox's ace again.  

    The Red Sox have about $15.75 million per year devoted to Beckett through 2014.  They still have faith in him to lead this re-tooled Red Sox squad.

12. Nate Robertson

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    LAKELAND, FL - MARCH 03: Nate Robertson #29 of the Detroit Tigers pitches against the Cleveland Indians during a Spring Training game on March 3,2007 at Joker Marchant Stadium in Lakeland, Florida. (Photo by Rick Stewart/Getty Images)
    Rick Stewart/Getty Images

    Nate Robertson 'STOLE" $7 million per year from the Detroit Tigers back in 2008.  As a number 4/5 starter, Robertson was subpar at best for the Tigers.  Throughout his career he's posted a pitiful 57-77 record and fooled the Tiger organization.  Not only did Robertson have a poor record, but his ERA consistently sat around 6.00

    If nothing else, at least Robertson is flexible in the fact that he can pitch as both a starter and reliever.  But be honest, would you want him in as either?  At the time, this was stunning for a guy coming off of a 9-13 season to boot.  

11. Gary Sheffield

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    BOSTON ? MAY 23:  Outfielder Gary Sheffield #11 of the New York Yankees swings at a Boston Red Sox pitch during their game on May 23, 2006 at Fenway Park, in Boston Massachusetts. The Yankees won 7-5.  (Photo by Al Bello/Getty Images)
    Al Bello/Getty Images

    As part of a "sign and trade" from the Yankees to the Tigers, Gary Sheffield signed an extension for $28 million over two seasons.  By then, Sheffield's career was practically over, which made this contract meaningless.  Sheff's better days were behind him and the Tigers were left in some debt for this deal.

    The Gary Sheffield of the Florida Marlins days was long gone by 2007.  He was on the decline and the Tigers suffered because of his contract.  Soon thereafter, Sheffield would be named in the Mitchell Report.  

10. Austin Kearns

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    LOS ANGELES - MAY 7: Austin Kearns #25 of the Washington Nationals hits a two-RBI double in the eighth inning against the Los Angeles Dodgers on May 7, 2009 at Dodger Stadiium in Los Angeles, California.    (Photo by Stephen Dunn/Getty Images)
    Stephen Dunn/Getty Images

    After a couple of solid seasons, the Nationals believed in Kearns, their midseason acquisition from the Cincinnati Reds.  They'd believed in him enough to think that he was worth nearly $6 million per year for three seasons.  This didn't pan out as they could have hoped and now Kearns, at age 30, is again looking to resurrect his career.

    The Nationals made a major league mistake in giving Kearns this type of money.  His floundering production was clear in year two and he never recovered from injuries in 2008 and 2009.  After his dismissal from the Nats, Kearns made his way to Cleveland, then eventually to the Yankees in 2010.

9. Jake Westbrook

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    CLEVELAND - OCTOBER 15:  Starting pitcher Jake Westbrook #37 of the Cleveland Indians points to ask the umpire to check the swing of the first batter Dustin Pedroia #15 of the Boston Red Sox in the first inning of Game Three of the American League Champio
    Elsa/Getty Images

    While he may be a decent option as a low-end starter, he's certainly not a top-of-the-rotation guy that the Indians made him out to be in 2007.  He's since been traded to the St. Louis Cardinals and remains a member of the Cardinals for the next few seasons. 

    Westbrook had had some good seasons with the Tribe but certainly wasn't worth the $11 million per year that he received.  Looking back, this one is laughable.  Westbrook had already been under contract and had his deal re-worked.  He's had Tommy John surgery during this contract and never was able to fully hold up his end.  Otherwise, he's barely been a .500 pitcher since.  

8. Bobby Crosby

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    MESA, AZ - MARCH 03:  Bobby Crosby #7 of the Oakland Athletics bats against the Chicago Cubs during the spring training game at HoHoKam Park on March 3, 2009 in Mesa, Arizona. The Cubs defeated the A's 6-4.  (Photo by Christian Petersen/Getty Images)
    Christian Petersen/Getty Images

    After an exceptional rookie season in 2004, the Oakland A's vested a great deal of their future into Bobby Crosby.  Though the contract was only worth about $2.5 million per year for five seasons, the A's were dead wrong and Crosby faded quickly.  

    Crosby never was able to regain the magic of his Rookie of the Year campaign and suddenly disappeared from Oakland.  This was a mega disappointment for the A's who really were banking (literally) on Crosby's growth and production for them.  

7. Derek Jeter

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    ARLINGTON, TX - OCTOBER 15:  Derek Jeter #2 of the New York Yankees gestures against the Texas Rangers in Game One of the ALCS during the 2010 MLB Playoffs at Rangers Ballpark in Arlington on October 15, 2010 in Arlington, Texas.  (Photo by Stephen Dunn/G
    Stephen Dunn/Getty Images

    The New York Yankee captain Derek Jeter is one of the best players of this era.  Regardless, he nor the Yankees can be overlooked in their 2000 extension.  This deal saw Jeter earn about $20 million over a decade and was surprising to a degree.  For a shortstop that isn't all that good defensively, this was a little too much to pay.  Since then, the Yankees have won only one World Series title.

    There's no questioning Jeter's leadership and clutch play, but his defense has always been suspect.  It's tough to include him on this list for a few reasons.  But in the end, when considering the amount of money involved, it's tough to argue that this was a bad deal.  The Yankees would never be able to replace his leadership but the commitment was steep and even for Jeter this one is tough to justify.  

6. Ryan Howard

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    SAN FRANCISCO - OCTOBER 20:  Ryan Howard #6 of the Philadelphia Phillies prepares for an at-bat against the San Francisco Giants in Game Four of the NLCS during the 2010 MLB Playoffs at AT&T Park on October 20, 2010 in San Francisco, California.  (Photo b
    Justin Sullivan/Getty Images

    This deal is an albatross for the Phillies and will remain so for the next several seasons.  Ryan Howard is one of the top power hitters in the game, but the fact that he'll be paid $25 million over the next five seasons is absurd.  For starters, Howard's 2010 season was not very "Howard-like."

    With Howard's fat new contract, it became impossible for the Phillies to even consider re-signing Jayson Werth.  This deal could pay off, but it's hard to ignore it's size more than anything.  For a first baseman that's a "typical" power hitter, (strikes out/hits home runs) this is a poor deal for the Phillies.  Hopefully, to prove Ruben Amaro Jr. at least "semi-right," Howard will perform through his contract.    

5. Vernon Wells

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    TORONTO, ON - SEPTEMBER 29: Vernon Wells #10 of the Toronto Blue Jays hits against the New York Yankees during a MLB game at the Rogers Centre September 29, 2010 in Toronto, Ontario, Canada. (Photo by Abelimages/Getty Images)
    Abelimages/Getty Images

    Vernon Wells' seven-year, $126 million deal is still puzzling even in its fifth year.  Considering that Wells has yet to lead the Jays to the playoffs, this is a very bad extension.  To many, it was already risky to begin with, ultimately though, Wells has not performed.  

    Since his contract, Wells has rather been on the decline.  Each season, it's more and more apparent how much this deal hampers the Jays.  J.P. Ricciardi wasn't necessarily good for the Jays either.  This deal, along with others, proves that.  

4. Ken Griffey Jr.

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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

    Ken Griffey Jr. possesses the most natural swing ever.  He's one of the best players the game's ever seen too in my opinion.  His deal shouldn't have turned out the way it did.  Griffey's many injuries turned this deal for worse and made the Reds really regret it when they acquired and extended him from Seattle. 

    Griffey missed about three seasons or more due to injury and wasn't able to fulfill his contract.  Talent was never the issue but rather staying on the field.  His career went into decline while he was still in his prime so we never saw this great athlete in his "true" prime.

3. Troy Tulowitzki

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    ST. LOUIS - OCTOBER 2: Troy Tulowitzki #2 of the Colorado Rockies throws to first base 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
    Dilip Vishwanat/Getty Images

    Troy Tulowitzki has all of the tools to become one of the best all-around shortstops ever.  Even so, his deal this past season, which keeps him as a Rockie through 2020, is insane.  This $134 million extension has many across the baseball world shaking their collective heads.  The Rockies needed to start somewhere, but this commitment to Tulo wasn't the answer. 

    He's definitely the best power-hitting shortstop in the game today, but does a lot of this come from his playing in Coors Field?  Tulowitzki had been under contract until 2013 on a six-year, $31 million deal, but this revamped deal trumped that.  

2. Eric Chavez

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    ANAHEIM, CA - MAY 14:  Eric Chavez #3 of the Oakland Athletics looks on prior to the start of the game against the Los Angeles Angels of Anaheim at Angel Stadium on May 14, 2010 in Anaheim, California.  (Photo by Jeff Gross/Getty Images)
    Jeff Gross/Getty Images

    This one is Billy Beane's worst running away.  Eric Chavez's extension has held the A's down for years and mercifully ended this past season.  The six-year, $66 million deal that he received in 2004 can not possible be explained.  The deal even included a club option for 2011 which the A's respectfully declined.

    Chavez was a highly regarded player in the organization for several years before this deal.  Then, the wheels started to come off for Chavez.  He never performed up to the standards of his contract and now hits the free-agent market.  Despite several injuries, there's no other reason why Chavez's poor play over the past few years.  

1. Alex Rodriguez

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    NEW YORK - JULY 19:  Alex Rodriguez #13 of the New York Yankees looks on from the dugout during the game against the Seattle Mariners at Yankee Stadium July 19, 2006 in the Bronx borough of New York City. The Mariners defeated the Yankees 3-2.  (Photo by
    Jim McIsaac/Getty Images

    Alex Rodriguez is a great player without a doubt, but he's been laughing to the bank for the past decade and will continue to do so.  A-Rod's extension in 2007, 10 years of $275 million payment is a whole lot. He nearly makes more in one season than the Pittsburgh Pirates' entire team did in 2010.  How can you explain that?  Especially when he's not even the top player in the game.

    A-Rod makes more than three times what the average Yankee makes and that's saying something.  His extension, at age 33 was mind-boggling.  To think that the Yankees have him locked up through 2017 is really something.  He's now their own personal albatross for the next seven years.