[iframe width="560" height="315" src="https://www.youtube.com/embed/cQrVrAZSQaY" frameborder="0" allowfullscreen] All but one of the moments that were ranked in this list fall under three categories: postseason heroics, perfect games, or historic moments in Yankee history. Jason Giambi's 14th inning home run against the Minnesota Twins in an otherwise unremarkable May game is the exception.
The Yankees had signed Jason Giambi to one of the largest average annual values in MLB history. After watching the dynasty team start to age and whither, the Giambi signing signaled the beginning of the Evil Empire phase for the New York Yankees--a big enough move to inspire Billy Beane to attempt the radical transformation of the post-Giambi A's depicted in Moneyball. Giambi replaced a beloved player with his fair share of clutch postseason moments in Tino Martinez. Going into the game, Giambi was off to a slow (for him) start, and people were starting to question if he could handle the pressure of playing in New York.
But really, we don't need all that off-field drama to make this an amazing baseball moment. The game and the home run that ended it stand on their own.
The game was epic even before the ending. The Yankees gave up a 5-run lead in the 6th inning, but a Bernie Williams home run tied the game in the 9th off Eddie Guardado to force extra innings. After Sterling Hitchcock allowed 3 runs in the bottom of the 14th, the game looked lost. But then the Yankees loaded the bases with 1 out, and Jason Giambi hit an absolutely bomb to center field. Check out this insane WPA chart from Fangraphs:
We all dream about hitting a walk off-grand slam down 3 runs in extra innings, but it almost never happens. The only other Yankee ever to hit a game-winning grand slam down three runs was Babe Ruth.