LACHLAN CARTWRIGHT detested the silly routine. As a New York Post reporter, he often dealt with a nightclub publicist who, like clockwork, would relay a list of the previous evening's notable guests. The briefing didn't simply mention the celebrities present; it also included details on the kind of sauce they put on their steaks and the brand of vodka they sipped. But one boldfaced name always seemed to be missing: Derek Jeter.
Even if multiple tipsters had spotted the Yankees shortstop, Cartwright could rarely confirm his presence. The mere suggestion that Jeter might've been there caused the flack to get cagey and blurt, "You can't run that."
"We can't run what?" Cartwright says, smacking the metal table outside a lower Manhattan coffee shop for emphasis. "We are a newspaper: We can run what we bloody well like to."
"It was very clear," Cartwright says, "that he was a protected species."
Cartwright wasn't angry. He was incredulous. After all, as a Post and Daily News veteran who is now executive editor of Radar Online, he is a big-game hunter. And Jeter has been more elusive than anyone he's ever tracked. "There were only two people I came across in that space," Cartwright says: "Leonardo DiCaprio and Derek Jeter."
Typically, the less we know about a public figure, the more we speculate. But Jeter is no ordinary celebrity. Even Post gossip column Page Six—which once ran (and later corrected) a blind item implying that Sandy Koufax was gay—won't dish wildly about him. "If he has any flaws," former Page Six editor Richard Johnson said in an email, "I'm unaware of them."
At this point Jeter's ability to sidestep controversy is as much a part of his lore as his hit total or The Flip Play. And despite playing in the nation's biggest city and harshest media market for two decades, dating pop stars and actresses, and answering reporters' questions before and after games as many as 200 times a year, he has effectively walled off his personal life.
Seth Mnookin spent more than four hours with Jeter for a 2011 GQ profile in which the writer called the All-Star "one of the nicest, most genuine celebrities" he's ever interviewed. Throughout the conversation Jeter remained cautiously affable—that is, until Mnookin brought up the shortstop's then girlfriend Minka Kelly. "I felt like I just crossed some line that I was not aware was there," Mnookin says. "His entire demeanor changed." Jeter didn't utter a word in response, but his look screamed, I'm about to knife you in the heart.
"He's the nicest guy you ever want to meet on the surface, but you're not getting past that," says Jeter's minor league teammate R.D. Long. "Every year that he's been there, he's had to put up another layer of protection."
To sportswriters, Jeter has been accessible in body but not always in spirit. He seldom publicly critiques anyone or anything. In July 2013, in a press conference held when Jeter briefly returned from surgery to repair a broken ankle he'd suffered the previous October, he was asked if it felt good to be playing in major league ballparks again. "It's a huge difference," he said, before stopping himself, then swiftly adding the caveat, "No disrespect to any rehab assignment."
IN THE 2010 buddy-cop comedy The Other Guys, Mark Wahlberg played a disgraced New York City detective. The movie's writers needed a crime to fit the character's shame. Naturally, director Adam McKay says, "we came up with accidentally shooting Derek Jeter in the leg." During filming on Coney Island, crowds gathered around the set—not just to gawk at Wahlberg and costar Will Ferrell but also to catch a glimpse of Jeter, who was shooting a cameo. "In New York City with Derek Jeter, Will's celebrity seems about a fifth as bright," says McKay, who also directed Anchorman and Step Brothers. "It was like you were hanging out with Louis XIV in France."
Jeter's composure and savvy in public are legendary—he seems to have been blessed with a politician's knack for working a crowd while simultaneously keeping his distance. In April 1997, Topps and artist Peter Max held an event to promote a series of baseball card portraits, and Jeter, the reigning AL Rookie of the Year, attended the event, held at Max's studio near Lincoln Center. Marty Appel, the Yankees' public relations director from 1973 to '77, emceed. He recalls watching the 22-year-old Jeter make eye contact with each guest he greeted, with a polish typically reserved for veterans. "I have seen it many times before," Appel says, "but I'm not sure I ever saw it on a player that young."
New York's obsession with Jeter only grew. Kristielee Wilcox claims she didn't head to Yankee Stadium with the intention of causing a scene, but on April 5, 2002, the day of New York's home opener, that's exactly what she did. Early that afternoon the 26-year-old from Long Branch, N.J., decided, I'm going to give Derek Jeter my phone number. She used lip liner to scribble down her digits on a scrap of paper, and in the eighth inning, she ran onto the field and handed it to the shortstop, who covered his face with his glove to conceal a smile. Security guards eventually wrangled Wilcox off the field. That summer she missed her court date, got arrested and ended up spending a night in jail. But she did make the cover of the Post.
By then Jeter was used to the attention. But despite his high-profile romantic relationships—Mariah Carey, Jessica Biel, Kelly—he has largely avoided embarrassing publicity. After the 2009 season a photographer snapped pictures of Jeter and Kelly on vacation on St. Barts, and the Post splashed the "exclusive" images across the front page. There was nothing remotely scandalous about them, but they were rare. Justin Smith, an executive at FameFlynet, the celebrity photo agency that sold the images to the Post, estimates that in the last decade the company has acquired only about 10 sets of Jeter photos. (By comparison, FameFlynet has between 150 and 200 sets featuring Alex Rodriguez.)
Jeter has figured out how to fly under the radar. His circle of family, friends and trusted social venues is small—and quiet. That may explain why few club owners and publicists will gab about Jeter. "They're happy to see everyone else's name in the paper with their club," Cartwright says, "but they were afraid of the backlash from Jeter, [of him] saying, 'Hey, I'm not gonna come to your place anymore.' "
That fear may not be unfounded. For a stretch in the '90s, Jeter was close with Long, an infielder whom the Yankees also drafted in 1992. The pair were friends and teammates at two different stops in New York's minor league system—"A Frick-and-Frack combo," says Long, who never made the majors and now coaches. In 2004, Jeter attended Long's wedding. But then Long was quoted extensively in Ian O'Connor's definitive—but unauthorized—2011 Jeter biography, The Captain. Among other insights, Long offered this assessment: "Derek is the iciest non-icy person I've ever met." Since the book's release, Long says, he and Jeter "haven't really talked."
"There's nothing in there that's disparaging," Long says. But he understands why they've drifted: "He doesn't see the media as his friend."
Three years ago the Post ran an infamous story claiming that Jeter made a practice of handing out gift baskets of memorabilia to women who spent the night with him at his Trump World Tower apartment. Emily Smith, who wrote the item, says Jeter's camp didn't comment or complain. Unlike many celebrities, he rarely bothers shooting down gossip that makes him look silly. True or not, why keep the story in the news longer than it has to be?
Even Jeter's mundane daily routine could become tabloid fodder. In May 2013, after Jeter supposedly ordered his coffee at a Starbucks in Greenwich Village under the name Philip, the Post sent a reporter to try to find the barista who served the Yankees shortstop. The paper had no luck but still ran a giant photo of Jeter, mismarked cup in hand.
In August 2013 the Daily News published a photograph of Jeter's girlfriend Hannah Davis, who happened to be wearing a diamond ring. IS DEREK JETER OFF THE MARKET? the headline asked. "We took a bit of a punt with that," admits Cartwright, an Aussie who was working at the Daily News at the time. "And we did it in a calculated way that there would be no comeback on us if it turned out to be that they weren't engaged." They weren't.
"If the headline has a question mark," Cartwright says, "the answer is always no."
JETER HASN'T exactly loosened up as he's aged, but his cautiousness has been bolstered by touches of humor. A few seasons ago former Wall Street Journal reporter Tim Marchman decided to write about the prospect of Jeter's breaking Pete Rose's career mark of 10,328 outs recorded, and asked the shortstop for his thoughts on the subject. "I'll let you have fun with that," Jeter said, and ended the conversation.
"There was nothing hostile about it or anything. He just seemed kind of amused," Marchman, now an editor at Deadspin, said in an email. "It would have been totally fair to get hostile, or to say, 'Hey, you have to be pretty good to make that many outs.' But he just refused to engage, totally smooth. He's what p.r. people desperately try to train their clients to be, and it's totally natural to him."
In fact, Manhattan communication firm Kwittken shows video of Jeter's press conferences to clients. The company's CEO, Aaron Kwittken, says that Jeter smartly treats interviews not as conversations, but as highly choreographed exchanges of information. "If you look at everything as a transaction," Kwittken says, "you're able to make better decisions."
Of course, that method doesn't work for everyone. Gary Sheffield, Jeter's teammate from 2004 to '06, spent many clubhouse sessions sparring with reporters. The shortstop's advice for him? "Basically, 'Just be boring,' " Sheffield recalls. "And I was looking at him, and I'm like, 'Just be boring'? I said, 'There's nothing boring about me.' "
Jeter may not actually be boring, but that's what he wants reporters to see. Even in his final days as a Yankee, he remains in perfect rhythm. Now a broadcaster on the YES Network, former teammate Paul O'Neill still marvels at Jeter, whose seasonlong farewell tour has consisted of a daily barrage of interviews and appearances. "This is just his day now," O'Neill says. "By 7:10, he'll be completely focused on the game."
Soon Jeter will be out of the spotlight. He will be remembered for two things: his on-field résumé, which will land him in the Hall of Fame, and his persona, which every New York superstar who follows him will try to emulate. "That guy is the model," Mets ace Matt Harvey told Men's Journal in 2013. "I mean, first off, let's just look at the women he's dated. Obviously, he goes out—he's meeting these girls somewhere—but you never hear about it. That's where I want to be." The press hammered Harvey for those comments, and he backtracked, having inadvertently broken one of the shortstop's cardinal rules: Never reveal too much. Acting like Jeter takes astounding discipline.
This is why those who try to follow his path will likely fail. Jeter is, after all, a man seemingly born ready to handle his extraordinary life and celebrity. "You can't pretend for as many years as he's played," Sheffield says. "So basically all you have to say is, That's who he is."