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.