30 biggest free agent contracts in New York Yankees history

Aaron Judge Press Conference
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20. Derek Jeter, 2010: Three Years, $51 million

Jeter gets the edge over Posada here because of the AAV tiebreaker.

This was the winter where Jeter leaving the Yankees seemed as real as it ever became. This contract comes from the period chronicled in "The Captain" where Brian Cashman reportedly responded to Jeter's request to learn "who he'd rather have" at short by talking up Troy Tulowitzki.

It created bad blood, but the job got done. It always did.