Relive the Moments That Defined Derek Jeter’s New York Yankees Career

Memorable plays include 'the Flip,' 'the Dive,' and more.

Moments That Defined the Career of New York Yankee Derek Jeter
Derek Jeter #2 of the New York Yankees celebrates after a game winning RBI hit in the ninth inning against the Baltimore Orioles in his last game ever at Yankee Stadium on September 25, 2014 in the Bronx borough of New York City. (Elsa/Getty Images)

New York Yankee Derek Jeter‘s baseball résumé almost doesn’t seem possible. AL Rookie of the Year in 1996. Five World Series rings. World Series MVP in 2000. Fourteen trips to the All-Star Game. If the guy isn’t a first-ballot (or even unanimous) Hall of Famer, then who is?

On Sunday, May 14, the Yankees will be retiring Jeter’s jersey No. 2 at home in the Bronx. In honor of that occasion, ESPN put together some of the career-defining moments from Jeter’s tenure in New York. We’ve elected to include the top five—along with in-action video clips of each.

1996 ALCS Championship Home Run – October 9, 1996 (a.k.a. “the Jeffrey Maier Home Run”) – It’s these types of plays that are the reason the manager’s challenge is now a part of baseball. But back in ’96, there was no such thing, and this could’ve been the most famous ground-rule double of all time. But the umpiring crew called it a dinger.

2001 ALDS Game 3 – October 13, 2001 (a.k.a. “the Flip”) – Call this undisputed hustle. Sure, it was just a single out at home plate—the flip in question being from a charging Jeter to catcher Jorge Posada—but it was a momentum-changer, to say the least.

2004 Yankees vs. Red Sox – July 1, 2004 (a.k.a. “the Dive”) – Like “the Flip,” this play was for a single out, but showed off Jeter’s acrobatic athleticism in fielding his position. Grabbing a pop fly by the Sox’s Trot Nixon, Jeter dove headlong into the first row of the stands, emerging with a cut under his right eye. The Yanks would end up winning the game in extra innings.

2011 Yankees vs. Rays – July 9, 2011 (a.k.a. 3,000th hit) – It was inevitable. Jeter was in the twilight of his career and inching closer to the 3,000 hit club. And he couldn’t have picked a better way to join up: with a home run off of Rays’ staff ace David Price. Wow.

2014 Yankees vs. Orioles – September 25, 2014 (a.k.a. the Grand Finale) – Did you expect any less? In his final home game in a Yankees uniform, Jeter hit a walk-off single in the 9th to secure his team another victory.

—with additional reporting by RCL’s Will Levith

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