Derek Jeter’s 10 most memorable moments in Hall of Fame Yankees career, including flip play and 3,000th hit

Wednesday afternoon, New York Yankees legend Derek Jeter will be inducted into the Baseball Hall of Fame in Cooperstown, New York. The induction is a long time coming for Jeter, who was one vote shy of being selected unanimously in January of 2020. The 2020 induction ceremony was pushed back due to the COVID-19 pandemic, but Jeter, Larry Walker, Ted Simmons and Marvin Miller will join the greats in Cooperstown this week. Here’s how to watch.

Jeter won five World Series championships (1996, 1998-2000, 2009) with the Yankees, and he is sixth all-time with 3,465 career hits and seventh all-time in WAR among full-time shortstops. Here’s the career WAR leaderboard among players who played at least half their games at shortstop:

1. Honus Wagner — 113.8
2. Cal Ripken Jr. — 95.6
3. Robin Yount — 77.0
4. Ozzie Smith — 76.6
5. Luke Appling — 74.2
6. Arky Vaughan — 72.4
7. Derek Jeter — 71.8
8. Alan Trammell — 70.7
9. Barry Larkin — 70.2
10. Pee Wee Reese — 66.4

Oddly enough, given all that he accomplished his career, Jeter does not have one “signature moment,” so to speak. He has signature moments. Plural. Jeter’s career was truly storybook. You couldn’t script it any better. The championships, the accolades, the history. Jeter was the last true face of baseball, I’d say.

So, with all that in mind, let’s look back at the most iconic moments of Jeter’s Hall of Fame career. Here are his signature moments — again, plural — listed chronologically.

1. Oct. 6, 1996: The Jeffrey Maier home run

Back before the days of instant replay, the on-field umpires ruled the land, and their calls stood. There were arguments. Boy, were there arguments. But good luck getting an umpire to change his call.

In Game 1 of the 1996 ALCS against the Baltimore Orioles, Jeter hit a solo home run in the eighth inning to tie the game 4-4. The ball did not actually clear the fence. A young fan named Jeffrey Maier reached over the fence and caught the ball before it could settle into right fielder Tony Tarasco’s glove. Right field umpire Richie Garcia ruled it a home run. Tarasco and O’s manager Davey Johnson went bonkers.

The home run stood, and the Yankees went on to win the game in 11 innings on a walk-off home run by Bernie Williams. They would later win the series in five games before beating the Atlanta Braves in six games in the World Series.

An incorrect call? Absolutely. But there was no replay at the time, so the call stood.

2. Oct. 25 & 26, 2000: Subway Series homers

The 2000 World Series was a very big deal in New York. A bigger deal than most World Series. The Yankees and Mets met in the Fall Classic that year, so bragging rights in the city were on the line. Fans ate it up. The Yankees had won three of the previous four World Series, and the upstart Mets were trying to unseat them as the world champs.

The Yankees won the first two games of the series before the Mets rallied to win Game 3. The Mets had the momentum heading into Game 4 at Shea Stadium. Jeter then took it all away by hitting the first pitch of the game over the wall for a leadoff home run.

The Yankees went on to win Game 4 by the score of 3-2 to take a commanding three-games-to-one series lead.

One day later, Jeter hit the game-tying home run in the fifth inning of Game 5. The Mets never led again in the series.

The Yankees went on to win Game 5 4-2 and the series for their third straight championship. New York would remain a Yankees town.

3. Oct. 13, 2001: The flip play

This is maybe the most memorable individual play of Jeter’s career. It is certainly the most memorable defensive play.

In the seventh inning of Game 3 of the 2001 ALDS against the Oakland Athletics, Jeter ventured out to the right side of the infield to serve as an emergency cutoff man. He reeled in Shane Spencer’s airmailed throw from right field and flipped it to Jorge Posada at the plate. Posada tagged Jeremy Giambi out at home.

Jeter and the Yankees insist they practice that play. It’s part of their regular spring training activities even to this day, so Jeter did not do anything out of the ordinary. He was right where he was supposed to be, as far as they’re concerned. Of course, you never see a shortstop there, which is what makes this so special.

Context is important too. The Yankees were down two games to none in the best-of-five series at the time, and they were nursing a 1-0 lead in Game 3. Jeter’s flip play cut down the tying run at the plate. The Yankees went on to win that game 1-0. They came back to win the series in five games.

4. Nov. 1, 2001: Mr. November

For the first time in history, baseball was played in the month of November in 2001. The Sept. 11 attacks pushed the schedule back and people throughout the country turned to baseball as a coping mechanism.

The Yankees were down two games to one heading into Game 4 of the 2001 World Series against the Arizona Diamondbacks, and they were one out away from a three-games-to-one series deficit when Tino Martinez hit a game-tying two-run home run off D-Backs closer Byung-Hyun Kim. That sent the game to extra innings.

A few minutes after the clock struck midnight and October 31 became November 1, Jeter ended Game 4 with a walk-off home run.

That was the final pitch of a nine-pitch at-bat. The Yankees tied the series at two games apiece, though they went on to lose the World Series on Luis Gonzalez’s walk-off single in Game 7.

5. July 1, 2004: The crash into the stands

To date, this remains one of the most exciting regular season games I’ve ever seen. The pitching matchup was lopsided (Pedro Martinez vs. Brad Halsey), yet the Yankees jumped out to an early 3-0 lead. The Boston Red Sox eventually rallied to tie things up and send the game to extra innings.

With the go-ahead run at second base and two outs in the top of the 12th, Red Sox outfielder Trot Nixon lifted a pop-up into foul territory, a pop-up Jeter ran down before crashing into the stands.

An overrated play? Yeah, possibly. I’ve seen some call it a great catch with a bad dismount. That said, this one is memorable not only because Jeter crashed into the stands, but because it stranded the go-ahead run in scoring position. The Yankees went on to win the game in 13 innings on a walk-off double by backup catcher John Flaherty.

6. Sept. 16, 2008: All-time Yankee Stadium hit king 

The old Yankee Stadium closed its doors in 2008, and during the final homestand, Jeter passed Lou Gehrig as the ballpark’s all-time hit king with a single to left field.

Here is the all-time hits leaderboard at the old Yankee Stadium:

1. Derek Jeter — 1,274
2. Lou Gehrig — 1,269
3. Mickey Mantle — 1,211
4. Bernie Williams — 1,123
5. Joe DiMaggio — 1,060

That is some set of names, isn’t it? Three Hall of Famers, one future Hall of Famer, and one of the most productive switch-hitters in recent baseball history. 

7. Sept. 21, 2008: Farewell to the old Yankee Stadium

A few days after becoming the ballpark’s all-time hit king, Jeter and the Yankees said goodbye to the old Yankee Stadium. The final game was played on Sept. 21, 2008, and after the Yankees beat the Orioles, Jeter and the team took a lap around the field as everyone said goodbye to the historic ballpark.

Jeter then took a microphone and addressed the fans with a heartfelt speech.

“Although things are going to change next year and we’re going to move across the street, there are a few things with the New York Yankees that never change,” said Jeter. “That’s pride, tradition, and most of all, we have the greatest fans in the world. We’re relying on you to take the memories from this stadium and add them to the new memories we make at the new Yankee Stadium and continue to pass them on from generation to generation. We just want to take this moment to salute you, the greatest fans in the world.” 

8. Sept. 11, 2009: All-Time Yankees hit king

One year after passing Gehrig for the most hits in Yankee Stadium history, Jeter passed him on another list, this time becoming the all-time hits leader in franchise history. He did it with a single the other way, a Jeter trademark, against Orioles right-hander Chris Tillman.

That was the 2,722nd hit of Jeter’s career. Here is the franchise’s all-time hits leaderboard:

1. Derek Jeter — 3,465
2. Lou Gehrig — 2,721
3. Babe Ruth — 2,518
4. Mickey Mantle — 2,415
5. Bernie Williams — 2,336

Basically a who’s who of all-time great Yankees.

9. July 9, 2011: 3,000th hit  

Amazingly, the Yankees did not have a single player with 3,000 career hits in their history prior to Jeter. Hard to believe given all the all-time greats who have worn pinstripes, isn’t it?

Jeter became the 28th player in baseball history to reach the 3,000-hit plateau, and he did it in style. He smashed a home run off then Tampa Bay Rays ace David Price. At the time, he was only the second player to go deep for his 3,000th hit, joining former Yankees teammate Wade Boggs.

Jeter singled in his first inning at-bat before hitting the home run second time up. His 3,000th hit was part of a five-hit game. The fifth and final hit drove in the go-ahead run in the eighth inning. It was a turn-back-the-clock game for late-career Jeter.

10. Sept. 25, 2014: The grand finale

Could it end any other way? In the final home game of his career, Jeter gave Yankees fans one final special moment, this one a walk-off single against the Orioles. (The Orioles seem to be on the wrong end of a lot of Jeter’s signature moments, huh?)

Here is how Jeter said goodbye to Yankee Stadium:

Classic inside-out swing by Jeter. He did that a couple thousand times in his career. Jeter announced his plans to retire earlier that year, so everyone knew it would be his final game, and that made it even more special. The anticipation had been building for months.

It should be noted that moment was made possible by a blown save. The Yankees took a 5-2 lead into the ninth inning, but closer David Robertson gave up a two-run home run (Adam Jones) and a solo home run (Steve Pearce), allowing the O’s to tie the game. That set up the Jeter walk-off in extra innings.

Best blown save in baseball history? I’m guessing Yankee fans don’t mind that one at all. Jeter’s farewell was a truly amazing baseball moment, one of many in Jeter’s storied career.

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