Red Sox vs. Yankees: Which Team Has the Most Brutal Contracts on Payroll?

Shaun TobackCorrespondent IOctober 12, 2011

Red Sox vs. Yankees: Which Team Has the Most Brutal Contracts on Payroll?

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    It’s all about risk-aversion in Major League Baseball. For most teams anyways.

    For most teams, survival is all about avoiding the massive, indefensible contract that can crush a franchise. But the New York Yankees and Boston Red Sox live in a different world.

    Boston and New York live in a world where risk-aversion is a mere suggestion, an old-wives tale that other franchises tell to make themselves feel better about losing.

    The truth is that part of the reason that the Sox and Yanks are so successful is that a big budget and a large market mean that greater risks can be taken.

    Fifty million dollars for the rights to talk to a completely unproven Japanese phenom? Sure! Why not?!

    Thirty-five million dollars for a glorified set-up man? Absolutely! Sign him up!

    From Daisuke Matsuzaka to Rafael Soriano, the examples of bad (i.e. non-risk-averse) contracts in Boston and New York are plentiful. The real question is this: Who has the worst contracts?

    What follows is a contract-by-contract, blow-by-blow comparison of the worst of the best. The contracts that would cripple other teams, but are mere obstacles in the way of greatness for the Yankees and Red Sox.

    *Disclaimer: As this is a comparison of terrible contracts, the “advantage” will be given to the team with the worst contract, not the best.

Carl Crawford vs. Alex Rodriguez

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    Last summer, Carl Crawford signed a $142 million contract with the Red Sox. It's been downhill ever since. Or uphill. Whichever the bad one is.

    Crawford seemed to feel the burden of his large contract, as well as the expectations that come with playing baseball in Boston. Only one year into his contract, many are wondering if he will ever be able to recover, and once again become the player he was in Tampa Bay.

    On the other hand, we have Alex Rodriguez, who perennially holds a vaunted position amongst the game’s most overpaid players. Heck, he holds a special place amongst the most overpaid humans on the planet, period.

    As the years pass, time seems to be treating Rodriguez unkindly. He is suffering through more and more injuries. His bat speed is disappearing. His power numbers are shrinking. In short, he is becoming less and less effective seemingly by the day.

    While Crawford’s contract is certainly an albatross, there are some silver linings for those who choose the see the glass as half full. He is still only 30 years old, which places him squarely in the middle of his prime. The raw tools (particularly speed and power) that enticed the Sox in the first place are likely still present, and could fully re-appear if he can overcome some mental and personal roadblocks.

    Although his first year with Boston was an unmitigated disaster, there is plenty of room and opportunity for improvement for Crawford.

    Rodriguez’s cause seems much more lost. He is aging quickly, and is still under contract to the tune of $20-plus million per year through 2017. That means that A-Rod’s putrid 2011 could be just the beginning of long process of disintegration that could haunt the Yanks for many years to come.

    Advantage: Yankees

Rafael Soriano vs. John Lackey

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    For many Yankee fans, the Rafael Soriano contract was questionable as soon as it was signed. After all, with the seemingly ageless Mariano Rivera continuing to dominate ninth innings, what is the point in paying any reliever $35 million?

    But any time a Yankee fan wants to feel better about Soriano’s contract, they need look no further than their AL East rivals, and their staff of overpaid pitchers who make Soriano’s deal look like something that was purchased during a sale at the dollar store in comparison.

    If John Lackey really was good, paying him $82.5 million would still be laughable. The fact that he is legitimately one of the worst starters in baseball puts his contract in the conversation with Barry Zito for worst in the game.

    Sure, Soriano’s deal doesn’t make much sense. But $35 million is chump change compared to the highway robbery that is Lackey’s contract.

    Advantage: Red Sox

Daisuke Matsuzaka vs. AJ Burnett

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    This is the heavyweight prizefight of laughable contracts.

    The Sox are paying Daisuke Matsuzaka $52 million to sit on the bench and work on his gyroball.

    The Yanks are stuck with A.J. Burnett’s $82.5 million deal.

    Neither player is worth a playoff roster spot, let alone the millions upon millions of dollars they are owed.

    Based on their annual salaries, it seems like this should be pretty clear-cut: Burnett's deal should be worse because he makes more than $30 million more than Matsuzaka for little more production.

    But then you factor in the $50 million that the Sox paid for the rights to negotiate with Daisuke when he made the move from Japan.

    Then you consider the fact that, even though Burnett was terrible at times this season, he was at least active and on the field. And although his effectiveness has waned (to put it mildly), he still has top-of-the-rotation stuff.

    Both Matsuzaka and Burnett have horrible mental makeups, but at least Burnett can (a) throw 96 mph and (b) stay healthy. Mark another one up for the Sox!

    Advantage: Red Sox

Mark Texiera vs. Adrian Gonzalez

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    Neither Mark Texiera’s nor Adrian Gonzalez’s contracts are true franchise-cripplers in the way that Burnett’s, Matsuzaka’s or Lackey’s are. But both players are still dramatically overpaid, especially considering their lack of postseason production.

    Would you rather pay Tex $180 million or Gonzo $154 million? It's really a matter of preference.

    If you consider both players to be basically equal, Gonzalez’s contract looks better than Texiera’s, but not by much (like I said earlier: $26 million equals chump change for these teams).

    Advantage: Draw


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    Under George Steinbrenner, the Yankees were the pioneers of trying to buy their way to a championship. They overpaid top-of-the-line talent year after year, regardless of how they fit into New York’s team concept, or how many prospects they had to give up.

    But in the last few years, the Red Sox have taken this concept to the next level. Case in point: Carl Crawford.

    When Boston signed Crawford, they weren’t really in need of another outfielder. Signing him didn’t address a need, or make the team dramatically stronger. This is the kind of attitude that leaves you with many of the worst contracts in your sport.

    The Yankees may have introduced baseball to the “spend, spend, spend” mentality, but the Red Sox have perfected it. And perfecting it in no way equates to wins.

    This is why the Red Sox are the “winners” of this contest. They have the worst contracts, have made the biggest mistakes and are in worse shape going forward.

    Congratulations, Red Sox! Here’s to a future filled with futility!