One of Aaron Boone's greatest moments as a player came in a Yankee uniform. Now, the Yankees skipper is on the other end of history.

Boone ended the 2003 ALCS with a walk-off homer against the Red Sox, sending the Yankees to the World Series. Fast forward 16 years later, and Boone is in the Yankees dugout, managing the club against Houston in Game 6 of the ALCS.

He watched as Houston's José Altuve ended the ALCS with a walk-off homer, sending the Astros to the World Series. And with that, Boone becomes the first person in MLB history to hit a series-clinching walk-off homer as a player, then lose on a series-clinching walk-off dinger as a manager (Elias Sports Bureau).