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

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Red Sox vs. Yankees: Which Team Has the Most Brutal Contracts on Payroll?
Nick Laham/Getty Images

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.

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