30 biggest free agent contracts in New York Yankees history

Aaron Judge Press Conference
Aaron Judge Press Conference / New York Yankees/GettyImages
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1. Aaron Judge: Nine Years, $360 Million

Bet on yourself. Earn $360 million. Listen to Hal Steinbrenner grovel from Italy before you sign the contract. Make the Yankee family squirm by talking to the Giants and Padres for a little too long. Commit arson. Gain the captaincy.

Aaron Judge, you did it. AL home run record. Largest deal in Yankees history. Now comes the hard part.