Derek Jeter has checked off nearly his entire baseball bucket list, winning five World Series and seven pennants during two decades with the Yankees, the last ten as team captain.

He is a member of the 3,000-hit club, won Gold Gloves and Silver Sluggers, was an All-Star Game and World Series MVP. His No. 2 has been retired by the Yankees, and he has a plaque in Cooperstown as a first-ballot Hall of Famer, which came in almost unanimously.