Yankees: Ranking Derek Jeter’s Most Iconic Moments

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.

2. The Mr. November Homer

Derek Jeter earned his iconic moniker Mr. November in 2001 with a home run for the ages.

On October 31, Tino Martinez and Derek Jeter likely locked eyes at some point late into the evening, and in tandem decided that, after four titles in five years, a still-buried-in-the-rubble New York hadn’t had their faith properly rewarded yet.

Or, at least, that’s what it felt like to a loyal fanbase who could not believe it was all happening again (and wait ’til they got a load of the next night).

Enjoy, the only moment in MLB history that comes equipped with its own set of ominous chimes.

With two outs in the ninth, Tino Martinez set the table perfectly, drilling a fastball into the outer reaches of the center field bleachers, with the black seats in sight, to tie the game. Then, with the contest stretching past midnight and in danger of advancing past the Martinez cut and swinging its momentum back to Arizona, Jeter made sure that none of the iconography was squandered. He didn’t hit home runs terribly often, remember. It was rarely Jeter’s job to complete the whole rally himself with two outs and no one on base.

Also — important — zero Yankees were doing any hitting whatsoever during the 2001 World Series.

Luckily, this inside-out swing had a bit more jolt on it — this horsehide ball had enough lift that it would’ve comfortably smacked a properly-situated Jeffrey Maier right in the sternum, beyond the wall. Just like that, the series was even. New life. No reason to die. A deflated Curt Schilling, who started the game, was forced to watch his hard work unravel, shred, and implode. It was at that very moment that he retreated to the clubhouse, asked Jeeves, “Can Heinz ketchup look like dried blood?” and plotted his unfortunate revenge.

Don’t let Andy Pettitte tipping pitches and Luis Gonzalez taking advantage of a drawn-in infield taint this memory for you one bit. This was for your city. This will stand the test of time.

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.