30 biggest free agent contracts in New York Yankees history
12 of 31
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.