Yankees: Ranking Derek Jeter’s Most Iconic Moments

New York Yankees legend Derek Jeter produced too many iconic moments to count, but we tried.

If you’ve ever spent any time on the internet (a bad place, don’t recommend it), you’ve likely run into haters and fans of lowlier franchises wasting their time debating and minimizing Derek Jeter’s merits. “What if Derek Jeter played for the Brewers? Huh? You ever think about that? I do constantly,” writes a random A’s fan, or an Orioles fan, or a Rangers fan. Or, as I like to call ’em, The Vanquished.

Because, you see, Derek Jeter didn’t play for the Brewers, the Reds, or any of the other teams in MLB. He was a New York Yankee, leading his team to the biggest stage annually, and delivering with frightening regularity, flicking the rest of the AL’s very cute playoff teams aside. Perhaps, if he had been a Brewer, Milwaukee would’ve won five Miller Lite-doused championships. These things just happened to Derek Jeter.

Sorry, correction: happened very much because of Derek Jeter.

Every New York child of the ’90s had a hero — mine was Paul O’Neill, because I guess, deep down, I admired someone fueled by a mean streak, and someone whose athletic talents seemed to come much less naturally, always with a piercing grunt. But every group needs a matinee idol, and it was Jeter’s job to both lead the PR efforts and perform. And man, oh man, he always balanced both spectacularly.

It’s a near-impossible task, but I’ve attempted to rank the snapshots of Jeter’s time-honored career that really embodied his sense of the moment.

(Honorable Mentions: The Red Sox Seats Catch, The Oakland A’s Seats Catch [similar, never mentioned!], The Bobby Jones HR, The 2000 All-Star Game, Each and Every Jump Throw [tied for sixth], The 2006 Shoulda-Been-MVP Season)

5. The Jeffrey Maier Homer

New York Yankees Hall of Famer Derek Jeter’s first iconic moment is an easy No. 5.

OK, I’ll come right out and say it — the Jeffrey Maier homer makes me a little uncomfortable.

It’s unquestionably iconic — a rookie’s arrival marked by a game-tying home run in Game 1 of the ALCS against an AL East rival, mysterious circumstances, an angry opponent. But, the bottom line is…this wasn’t a home run. Shouldn’t have counted. Oopsie.

I pine, though, for the days when every break went the Yankees way — so often these days it feels like they do all the work, put themselves in the right position, and then everything bends in the opposite direction (or buzzes, if you’re in Houston).

This is still a powerful entry for Deej into the American lexicon — and, by the way, winning Games 3, 4, and 5 on the road is still more impressive than anything from the series’ first two games. Never let anyone tell you Baltimore folded after this mistake — they rebounded to win the second game, then the Yankees kicked into 12 more gears. And it wouldn’t have happened without this myth-maker.

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4. Jeter Walks Off the Orioles

Derek Jeter walking off the Baltimore Orioles in his last game at Yankee Stadium was magical.

This was magic. Magic! M-A-G-I-C.

You remember where you were, you remember how you got there, you remember how you felt. How your body shuddered. You probably started filming your TV? Why? Who knows.

Downgraded slightly because O’s reliever Evan Meek grooved a fastball a bit, and because the 2014 Yankees were stuck in the mud and playing out what felt like a Memorial Campaign instead of a baseball season (Antoan Richardson scores?!), but it was hard to believe everything that authentically fell into place to make this happen.

First, Jeter reached base on a two-run error in what was likely his final at-bat (under normal circumstances) in the seventh. Coming back from a comedy show, I ducked into a random bar to watch it, got appropriately emotional, and bounded down into the subway, assuming everything would be done and dusted by the time I got home. Then, David Robertson blew a three-run save chance (the easiest type of save chance!) on home runs by Adam Jones and…Steve Pearce. Of COURSE. Of COURSE it was Steve Pearce.

But, none of it mattered. It was just window-dressing. The spotlight found the man of the hour yet again, and he flicked one into the gloamin in Jeterian fashion. One more time.

Sidenote: what a hideous injustice that Jeter was forced that season to play his final games in Boston, a city where they’ve now unilaterally claimed they’ve “always respected him,” despite selling graphic NSFW Jeter-A-Rod shirts on Yawkey Way for a decade. Don’t let ’em get away with it.

3. Jeter’s 3,000th Hit

New York Yankees shortstop Derek Jeter’s 3,000th hit was classically improbable.

Once again, another spotlight moment for Jeter that was so out of character it ended up cycling back around to be entirely in character.

Jeter never hit more than 24 home runs in a single season, and only drilled six in total in 2011, so naturally, he took one of the league’s best lefties in David Price deep for hit No. 3,000.

Of course, he didn’t start that day at 2,999, nor did he end it at 3,000. In lockstep with the rest of his career trajectory, he celebrated a singular moment in the spotlight, took a bow, and then kept on ticking. Needing two hits to reach the milestone (following a rainout the day prior — and I would know, I rode a Metro North all the way to Yankee Stadium only to hustle on StubHub and turn immediately back around), he instead delivered five, including the game-winning single in the eighth.

2011 was a campaign held together by gum and masking tape for the Yankees, relying on starters like Freddy Garcia and Bartolo Colon to match Max Scherzer and Justin Verlander in October. Jeter had begun to fall off a bit, too, at age 37, but only comparatively, still hitting .297 and playing in 131 games.

Luckily, though, things got easier for David Price in the years to come, and he never got taken deep at Yankee Stadium ever again.

1. The Flip Play

Derek Jeter of the New York Yankees changed baseball history with The Flip.

Yes, he was in the exact right place at the exact right time, but it’s still difficult to do the exact right thing once you get there. And he was only in that place in the first place because of his own instincts and ingenuity. Nothing was more emblematic of Derek Jeter’s career.

Down two games to none in the 2001 ALDS, and up only 1-0 in the third game, the Yankees were on the verge of succumbing to the 102-win Oakland Athletics (and definitely should’ve been prepared to do so!). Behind Mark Mulder and Tim Hudson, the A’s had taken the first two games at Yankee Stadium. It was ok. New York City had been through a lot. It had been a devastating autumn. The Yankees had already given them so much. Moneyball could take their turn.

Except for, you know, the fact that that entire paragraph embodies a loser’s mentality, and Derek Jeter is staunchly allergic to my previous 100 words.

Collecting only two hits, New York won this third game, thanks to Jeter’s perfectly-executed shovel pass to Jorge Posada. Jeremy Giambi, a doofus of all doofuses (doofi?) chose not to slide as he approached the closest of plays. Posada whipped around and caught the back pocket of his leg (a deflating feeling we’ve all experienced in some capacity), inches from paydirt. Terrence Long sat on second like Fred Willard in “A Mighty Wind,” muttering, “Wha happened?!” to an uninterested Chuck Knoblauch.

It’s fine that Shane Spencer aimed and fired, apparently thinking home plate was located somewhere in the Oakland Coliseum’s expansive foul territory. Jeter was there to pick him up and change an entire postseason. Jeter was always there to do exactly that.