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Derek Jeter comes gliding out onto the concourse of Citizens Bank Park in Philadelphia and, hoo boy, if you’re a connoisseur of heckling, you have to be ready for a show. This is Game Three of the World Series, Phillies on an unholy roll through the postseason, their fans in the kind of lather on which they famously pride themselves. There’s a whole section, overhanging Tony Luke’s cheesesteaks, devoted to chanting “Asshole!” at anybody who passes by in the jersey of the opposing Astros; so much booing it’s hard to tell where the rancor is even aimed. And into this maelstrom, escorted by security and flanked by reps, enters Jeter, such an icon of hated New York that he might as well be a yellow taxi, to a chorus of…cheers? What the hell?
“Derek! Derek!” cry kids and grown men alike, pressing items to sign into Jeter’s hands as he makes his way toward an appearance on the Fox Sports broadcast set. There’s even an “O Captain! My Captain!”
One woman in Phillies powder blue mounts a valiant effort: “De-rek Je-ter,” she calls. You know the cadence: sometimes adoring, others, like this, mocking; either way, a song that feels almost timeless at this point, up there with “Take Me Out to the Ball Game.”
“De-rek Je-ter,” the woman sings, “Last time you played here, you lost.” But it’s weak sauce. She’s all but drowned out by the ire pouring down on Alex Rodriguez, variously Jeter’s friend, foe, and foil, who, along with the rest of Fox’s pregame crew, is on air about 10 yards away, completely inaudible in the throng around the stage. Same as it ever was.
If Derek Jeter were a country, the Lonely Planet guidebook would describe it as a “nation of paradoxes.” From the time he appeared on the scene, just shy of 21, he has seemed simultaneously to belong exclusively to the New York Yankees and to all of baseball. He is both eternal kid and elder statesman. His brand is both intense work ethic and effortless grace; deadly serious and, well…coolly serious. All these things remain exactly as they were upon Jeter’s retirement from the game nine years ago.
He’s dressed tonight in a slim gray Dior suit, a shirt whiter and stiffer than Tom Cotton, and gleaming black leather shoes, also Dior; not for Derek Jeter the ex-jock uniform of suit and sneakers. One only has to watch ESPN’s Get Up to know that retirement settles poorly on some athletes: the specialized muscles going unused, the bulk pooling or bulging in unexpected places, civilian clothes never quite looking right. At 48, Jeter is still plausibly recognizable from the report Yankees scout Dick Groch delivered of him way back in 1992, as a 17-year-old Kalamazoo phenom:
“Long lean sinewy body. Long arms, long legs narrow waist, thin ankles. Live ‘electric’ movements…. Flow on the bases.”
Granted, there’s a little more mass now, and a little less hair, but there’s no mistaking the flow any more than when Jeter ruled as the Diddy-anointed “prince” of turn of the century Manhattan. Famously, he maintained a scandal-free reign as one of the most eligible bachelors in the media capital of the world. “I just always looked at it as icing on the cake,” he tells me of the days of clubs, nightlife, and dating the likes of Mariah Carey and Minka Kelly. “The bottom line was I had a job to do. I was playing every day to keep my job.” Still, it was not only as a fully formed shortstop that he arrived in New York. He was, in a very old-fashioned and classic sense, a star.
Admittedly, at a remove—and especially if the Yankees happened to drive you mad—that same poise could read as boringness, the “class” as calculation, the sangfroid as just plain froid. In person, though, the real charisma is undeniable. As we navigate the maze of corridors, elevators, and stairwells that traverse the stadium, heads swivel and phones flash. This at a time when, with the possible exception of Aaron Judge, baseball’s biggest stars could stroll down Ashburn Alley without receiving so much as a flicker of recognition. Jeter stops frequently, signs whatever is handed to him, greets the elevator operator, the security guard, the kitchen workers as we rush through.
At one point, I am sitting next to him on the back of a golf cart, rocketing along the tunnel that curves beneath the stadium. On the ground next to us snakes an enormous rolled-up American flag and, in repose around it, the various official personnel who will soon unfurl it across the field: Army, Marines, Coast Guard, the Philadelphia police and fire departments. We speed past and watch as bulbs of recognition go off one by one—“Hey!” “Jeter!” “Look!”— and uniformed men and women stagger to their feet as we recede down the corridor, as though they’ve just seen MacArthur reviewing the troops.
In addition to his TV appearance, Jeter has a corporate meet-and-greet on tonight’s schedule. Standard endorsement stuff, but Jeter somehow makes it feel like a papal visit. When he arrives, a clutch of middle-aged men lingers in the center of the room, glassy-eyed and on edge. Each has thought too long about the one thing he is going to blurt out when he gets his moment shaking Jeter’s hand: This one’s wife was born in the same hospital as Jeter. Another has some kind of mutual connection to a town in New Jersey; the guy can’t stop himself from saying something about the reservoir there, words spilling out even as his eyes seem to be pleading with his mouth to stop.
Jeter is relaxed and engaged. He’s spent his life in rooms like this. When asked how long he will be in town, he says he needs to be back in Miami to pick up his daughters from school the next day.
“Always have to be at pickup. You miss pickup, you’ve got trouble,” he says.
One guy, clutching a tall boy of mango-flavored beer, is trying to get to the next level. He drifts alongside as Jeter moves to the table covered with balls and begins signing, barely looking down as his pen flies across their surfaces.
“So you probably have time on your hands…since that whole Marlins thing,” the guy says, referring to Jeter’s decision early last year to vacate his position as CEO and a partial owner of the Miami Marlins. But it’s like trying to strike a match on a bar of soap. Jeter just smiles as two workers swoop in, place an acrylic box over each ball, seal the cartons, and stack them carefully into a large blue suitcase, which is quickly spirited away. “I’ve got lots going on,” he says. “Too much.”
The guy gives up. A generation of sportswriters sympathizes. Complaining about Jeter’s locked-down interview style has become a journalistic genre all its own. For 20 years he was a relentless frustrater of New York back pages, unwilling to stir even the tiniest bit of muck. He has never been sullen or standoffish, as he points out, but neither has he felt the need to be one iota more informative than he has carefully decided to be. In his playing days, his stated policy was to answer every question once and then never revisit it. It is not a position he has felt compelled to revise in retirement. Last year, when he released his seven-part ESPN docuseries, The Captain, the project was so authorized a biography that it practically came with a notary stamp; its credits included Jeter’s agent, his agency, Major League Baseball, and The Players’ Tribune, the media company Jeter founded specifically to create an end run around traditional sports journalism. The project could be seen as a seven-hour attempt to say everything he’s willing to say about his career once, and then never have to address any of it again.
On a podium at the meet-and-greet sits the World Series trophy, primed for a photo op. Jeter catches sight of the thing, and you can almost see a Gollum-like glimmer in his eye as he drifts over to peer at it.
This is only the third baseball game that Jeter has been to this season. The others were the All-Star Game and a game at Yankee Stadium commemorating his induction into the National Baseball Hall of Fame. His abrupt resignation in Miami came after four seasons there; he says he needed a break.
A line forms to take photos. Jeter takes his position next to the trophy; a handler makes sure his head isn’t covering the Capital One logo behind him.
“Do I really have to pose with all these Phillies fans?” he jokes.
“You don’t have to smile,” says his handler.
But smile he does, until the last person has come through, some of them barely daring to look him in the eye. This is, of course, a business obligation, and, as with everything Jeter, there’s a deliberateness to all his gestures, a bit of Dale Carnegie. But he is nevertheless endearing, and, frankly, it’s a little confusing. Because, right up until the unfortunate, complicating circumstance of meeting the man, I would have told you, without hesitation, that I hated Derek Jeter.
“Such a strong word!” he says, when I tell him so. “I never looked at it as people hated me as a person. They don’t know me. And I think if they knew me, they wouldn’t hate me. They just strongly disliked the team I played for.”
Oh, but I beg to differ. To dislike implies a real, personal, human animus. That’s way more serious than the beautiful, unencumbered, irresponsible hatred that is one of the great joys of sports, just as is unquestioning, unconditional love.
It comes almost as a relief when I finally catch the faintest glimpse of the Imperial Stormtrooper that I thought I knew from years of watching him play.
“Are you a baseball fan?” he asks.
“I’m a Mets fan,” I tell him.
He waits a beat. Gives a little cluck.
“Mets were pretty optimistic this year,” he says.
“Yes,” I say, as evenly as possible. The Mets led the National League East for nearly the entire season before characteristically stalling down the stretch and being summarily ousted in the playoffs. “Yes, they were.”
“Well,” says Derek Jeter, “It’s a long season.” I swear I can see a twinkle in his eye.
Monster.
Not long after the game in Philadelphia— the Series wrapped now; the long, dark winter begun—Jeter and I meet again, for lunch in New York. He’s wearing loose blue pants and a long-sleeve T-shirt, both bearing the logo of Greatness Wins, the athleticwear company he recently started with the founder of Untuckit shirts, along with Misty Copeland and Wayne Gretzky—an intriguing squad of crime fighters if ever there was one. He looks as crisp and comfortable as he did in the suit, his stubble so consistent with the last time I saw him that its length might be measured by caliper.
New Yorkers at lunch are a cooler bunch than Philadelphians at a game, but there’s still a ripple of energy as we pass through the dining room. Jeter takes a seat at a corner table, back to the wall, facing out.
His eyes flit around the room. “I see everything when I’m out,” he says. To demonstrate, he lowers his voice and points out a prominent gossip-media personality, whom he asks me not to name, eating across the room. At another table, a businessman lifts his phone in a way that could be either checking a text or taking a surreptitious photo. “I see it all,” Jeter says.
One narrative has it that growing up a biracial academic and athletic star in 1980s Kalamazoo prepared Jeter for the scrutiny of playing in New York. He stood out. “You get stares. You get looks. You get people laughing and whispering and pointing,” he says. “You walk into a room when you’re five or six years old, and everybody’s staring at you.” If it left Jeter accustomed to handling attention, it also helped to instill his famous guardedness.
“Maybe it’s a character flaw, but it takes me a long time to trust people,” he says.
Is it a character flaw? I ask.
“Well, it’s gotten me to this point,” he says. “You can’t turn off and on who you are, right? I’ve just always had trust issues.”
Our lunch is at the steak house in his financial-district hotel; Jeter orders a filet mignon, butterflied, medium, side of mushrooms. He sold his last apartment in New York even before he retired, renting for the final two years of his contract. In truth, the Prince of New York was never exactly a New Yorker. He’d lived in Tampa since 1994, shortly after the Yankees drafted him. “As soon as the season was over, I’d be back in Tampa,” he says. In his long NY career, he set foot in Central Park all of three times, the same number of times he rode the subway: twice for photo shoots and once, improbably, for a trip from the Upper East Side to Lower Manhattan for the ticker tape parade celebrating his first World Series championship, in 1996. If he truly lived anywhere, it might as well have been in a sixth borough named Black Car. Back and forth he went—apartment tower to stadium—on his season-long circuit.
Still, he will forever be associated with the last days of what now feels like an almost premodern Gotham Golden Age: before tech bros, before 9/11; a time of newspaper wars and Sex and the City, but not yet everybody who moved to the city because of Sex and the City; Brooklyn, but not Brooklyn; hideous men like Giuliani and Trump, but still only locally hideous; maybe the last time that New York truly felt like the only place in the world where it really mattered to be prince.
“New York was the center of the universe,” Jeter says. “The Knicks had good teams. The Rangers had won. Then hip-hop took it to another level: Puff, Jay-Z. Now here come the Yankees, and we dominated for a period of time. It just seemed like all eyes were on New York and all eyes were on us.” It was heady for a 20-year-old sudden star. “You’d go to clubs or lounges and everyone was there. People you grew up watching: Denzel. Jack Nicholson. And they come over to you. They know you on a first-name basis! It’s a surreal experience when you’re that young and you’re having success. I don’t know if I can articulate how weird it is.”
Jeter has frequently said that his career would have been ruined had cellphone cameras been around. It’s a good line, but of course he spent half his career in the camera-phone era. It’s taken real discipline to maintain his privacy all these years. He remains exquisitely attuned to the potential of a headline, and quick to head it off. When I ask if he remembers running into Donald Trump in his Manhattan days (Jeter lived in a Trump building), the notion that he would even engage such a question is so absurd that he just laughs.
Part of the care that he takes to limit what he says stems from a somewhat unexpected horror of being labeled cocky or arrogant. He brings it up repeatedly: Self-confidence is good, in this construction; self-involvement is just another kind of weakness. “I get irritated with people that talk about themselves all the time,” he says. “Some players need to do it. Great. I hope they do well. But I just wouldn’t choose to hang out with them in my spare time. You do need to have inner belief. You don’t need to talk about it.”
In all of this, there is the distinct sense that retirement, traumatic for so many athletes, has changed very little in Jeter. He insists that his various business interests, which also include the virtual trading card marketplace Arena Club, are enough to scratch his competitive itch. “Sure, it’s not playing in front of 50,000 people, but it’s still finding a way to compete, setting goals, building teams. It’s the same thing,” he says. In Philadelphia, I’d asked if part of him wished he was on the field that night. His response had been instantaneous.
“Playing?! No!” he’d said, almost sounding surprised. “Maybe for the first few years if I could have woken up and played in the World Series, I would have. But I played 20 years! There hasn’t been a day I’ve missed playing the game.”
He does say that he regrets not taking more pleasure in his career while it was unfolding. “I was never really able to enjoy the journey, because it was always, What’s next? What’s next?” He still does not wear any of his World Series rings, because to do so would suggest some kind of fatal complacency.
Still, he doesn’t appear to connect that regret to any problem with intense competitiveness itself. Winning is, after all, the Jeter brand. I ask if anything since leaving the game has given him reason to revisit this absolute faith in the importance of victory. Does he still believe the axiom he was famous for as a Yankee? That anything less than a championship each year is an unmitigated failure?
“It is!” he says, definitively, before I can even finish the question.
I tell him that has always struck me as a little crazy. Aren’t there a million small victories to be proud of along the way? Isn’t, say, winning three out of seven games of a World Series pretty good? Don’t the other guys get to be good once in a while?
“Do you want to expect yourself to lose? Be content with mediocrity?” he asks. “No, it’s a failure. As an athlete, you only have so many years.”
We order coffee. Jeter glances at his phone for the first time. A late-season hurricane knocked out power to his Miami home, and he’s checking to see that it’s come back on. When he turns back, his position has softened a bit. “Being successful is winning. Being happy is winning,” he says. “I want to be happy.”
There’s a tendency to imagine Jeter as part of some gentlemanly old-school baseball past, but he is no nostalgist. He tells me that he believes in the necessity for many of the changes that Major League Baseball will institute this coming season to speed things up and inspire more offensive dynamism.
“You need to increase the action. It’s not how long the games are, it’s that you sit there for 20 minutes before the ball is in play,” he says. He especially hates the shift, which will be banned in 2023. As a contact hitter who prided himself on doing whatever it took to win, doesn’t he think hitters should have neutralized the shift themselves, by adjusting their approach?
“Hitters don’t get paid to do that,” he says. “Start giving huge contracts to guys who hit singles the other way, and they’ll learn to do it.”
There have been rumors about Jeter joining the Yankees broadcast team, but watching him on the Fox set—where the antics included David Ortiz throwing around fistfuls of money from a gold suitcase as part of a Fox sweepstakes promotion—it’s difficult to imagine him joining that kind of scrum. It would be like a president going back to the Senate.
As early as 2010, Jeter had an immediate answer to what he wanted his second act to be: owning a baseball team. By all accounts, he was a committed and imaginative CEO of the Marlins, the first and still only Black person to hold the position on a major league team. One of his first moves was to take every member of the front office into the clubhouse to introduce themselves to the players and explain what they did. He hired Kimb Ng as the first female general manager in the major leagues. He took Spanish lessons to better communicate with the Latin American players. The Marlins made the playoffs once during his tenure, but there was a general sense that principal owner Bruce Sherman was not sufficiently committed to spending enough to field a consistent winner.
“I liked it. It was a chance to learn another side of the business,” says Jeter. “It takes time. That’s one thing: learning to have patience. I mean, I don’t have patience. It’s tough. Really tough. You want things to happen right away, and they don’t happen right away. That can be frustrating.”
The one thing close to a concrete answer the guy with the mango beer got out of him was about moving back to New York. “I don’t like cold weather,” Jeter told him. “At the beginning of my career, I didn’t get to choose where to live. Now I get to choose.” Later, he tells me he meant that he wouldn’t uproot his family so soon after they moved from Tampa to Miami. “My wife would kill me,” he says of relocating again.
When we were in Philly, as we sat in the greenroom of the Fox production trailer before his television appearance, Jeter jumped on FaceTime to say good night to his kids. There was some bedtime negotiation. Moving to the makeup chair, he chatted with the makeup artist about her grown daughter.
“Tell me it gets easier,” Jeter said
“All we can do is be present,” she told him sagely.
That part he gets. When he was with the Marlins, Jeter would leave work every night at 5:30 p.m. for dinner with the family before heading back to the stadium for home games. He’s still figuring other parts out, like sleep. Jeter was once a champion sleeper. He gloried in it. Back in his playing days, when he worked nights, he would get home after a game, let the adrenaline wear off, and head to bed around 2 a.m. He’d wake to an alarm at 9 a.m., eat breakfast, and then go back to bed, setting another alarm for 1 p.m., when it was time to head to the park. “I would just sleep all day long,” he says.
Now he goes to bed early, knowing he’ll be up throughout the night. The girls sleep fine; the problem is him. “I hear absolutely everything. And when I hear something, I can’t go back to sleep,” he says. “Sometimes I dream about them doing something and I wake up, walk down the hall, check the cameras. Try to listen.”
Jeter worries about the kids’ adjustment to school after COVID. “We were overly careful during the pandemic. We didn’t go anywhere. And if anyone came to our house, we would say, ‘Stay away from the people.’ So then we got back into going to school, and they’re crying. We’re like, ‘What are you crying for?’ ‘The people!’ ” He smacks his forehead. “You spend all this time telling them to stay away from people, and then you’re dropping them off with strangers. You don’t even think about those things…. I’ve always said, ‘Being unprepared is my biggest fear in life,’ ” he says. “But you can’t prepare for this. You think you can, but you can’t. You’ve just got to sort of figure it out on the way.”
There is a difference in Jeter when he tells these stories about parenthood—the arena where “winning,” or even knowing at any given moment what that might look like, is at its most elusive. “I’m not even saying this for your story,” he tells me, a tacit acknowledgment of how on-script he usually stays. “I’m not trying to paint a picture that’s not there.” It’s the rarest moment of hesitation, as though, for once, he hasn’t yet performed his customary exercise of thinking through exactly how to present himself or how it will sound. I ask whether parenthood has made him reconsider anything about how he was raised. Famously, Charles Jeter never let his son triumph at any game they played, even when he was very little. Would Jeter let his daughters win? Whatever uncertainty he’s allowed himself to show vanishes.
“Let them win?!” he says, laughing. “Not a chance. You don’t ever want your kids to think that achieving something is easy. People say winning feels good, but why does it feel good? Because it’s hard!”
He’s back. And would we want it any other way? Now and forever. Der-ek Je-ter.
Brett Martin is a GQ correspondent.
A version of this story originally appeared in the February 2023 issue of GQ with the title “Derek Jeter Will Never Retire”
PRODUCTION CREDITS:
Photographs by Danielle Levitt
Styled by Mobolaji Dawodu
Skin by Lisa-Raquel using Tom Ford Beauty
Tailoring by Ksenia Golub
Set design by Cooper Vasquez at Frank Reps
Produced by Lindsey Gardner
Photographed at The Nines, NYC
Special thanks to Jeep\