Derek Jeter, The Aspiring Media Mogul (Who Dislikes Media), Reveals Next Big Swing
Austin Hargrave

Derek Jeter, The Aspiring Media Mogul (Who Dislikes Media), Reveals Next Big Swing

"I don’t miss playing,” he says, as the press-shy former Yankee leads new website The Players’ Tribune, where pro athletes break news (sorry ESPN) and his big-name backers are betting on a media home run.

This story first appeared in the August 7 issue of The Hollywood Reporter magazine. To receive the magazine, click here to subscribe.

On a warm Tuesday evening in mid-July, dozens of elite athletes pack a rectangular patch of faux grass turf on the roof of The Standard hotel in downtown Los Angeles. Among the partygoers: New York Rangers goalie Henrik Lundqvist; tennis star Caroline Wozniacki (in a white Grecian gown); race car driver Danica Patrick; tight end Julius Thomas (in a black fedora), who in March signed a $46 million contract with the Jacksonville Jaguars; 14-year-old Little League sensation Mo'ne Davis (with her mom, Lakeisha McLean); new Los Angeles Clipper Paul Pierce; and Alex Morgan, fresh from a World Cup victory. Though it's an exclusive affair, the menu is curiously unhealthy (mini cheeseburgers, fried mac-and-cheese balls, bratwurst hunks on toothpicks). And snippets of overheard conversation reveal frustrations of the athlete's life. Obstacles to romantic entanglements ("I tell her I'm going to crawl into bed with you at 3 a.m. and I'm out at 8 a.m.," a football player relays to a bespectacled pal). The sometimes mundane nature of the job ("I want to tell the truth," says an MLB veteran, "but how do I explain to a fan that I could give two shits about what's happening in the third inning?").

These are the kind of admissions that would never pass the lips of the party's host — the tall, slim man in the bespoke Nigel Curtiss jacket nursing ice water from a plastic cup at the end of the bar — at least not in the open where a reporter might be near. In fact, Derek Jeter — the revered New York Yankees shortstop, a 14-time All Star who led his team to five World Series titles — spent 20 years playing baseball in the most intense media market in the country without revealing much of anything about his personal life, save for what could be gleaned from the occasional paparazzi photo.

"I always knew that my job was to limit distractions for my team and not cause headlines," reasons Jeter, who retired after last season. "So I kept a lot of things to myself."

But on this day, the man who perfected the polite shutdown is putting himself out there in an effort to convince more athletes to share their stories on his website, The Players' Tribune (TPT). Launched in October, the site lets athletes speak in their own words — in written pieces, video interviews and podcasts — directly to fans, eliminating the interpretive agenda of the press pack. The site has become a source for first-person athlete accounts that increasingly are making news and driving headlines in a rapacious media environment: Los Angeles Lakers guard Steve Nash announced his retirement in a letter; Red Sox slugger David Ortiz refuted widespread PED allegations in a revealing as-told-to account; Milwaukee Bucks center Larry Sanders talked openly in a video interview about the anxiety disorder that caused him to bolt the NBA.

"It's a trusted place, a place where they can speak freely and not have to worry about how their words are twisted and turned," says Jeter, 41. And then, perhaps remembering he's talking to a journalist, he adds, "I'm not saying everyone twists and turns. But when they can speak openly and honestly, it's pretty amazing what people talk about."

Of course, the media raised a collective eyebrow when TPT launched, viewing it as an incursion on journalistic turf where hard questions and objectivity rule. That the site's first big get was a November piece by Tiger Woods excoriating a mocking faux interview by golf writer Dan Jenkins (Woods called it "a grudge-fueled piece of character assassination") only advanced this narrative.

"I've never said that we're trying to eliminate the media," asserts Jeter. "We're not covering day-to-day sports scores. We don't have sports highlights. This is completely different. We're starting the conversation. I think we can coexist."

And if the assumption was that Jeter himself was suddenly going to become "chatty," as The New York Times speculated in a headline, the media got that wrong, too.

"Yeah, I'm so chatty," laughs Jeter, who so far has only posted a few publisher's letters. "Their reaction was, I never said anything for 20 years and now all of a sudden I was going to be telling my whole life story. But this was not built for me. It was built for the athletes."

The $40 billion sports industry has changed dramatically since the New York Yankees signed Jeter in 1992, right out of high school in Kalamazoo, Mich. Social media, mobile devices and the explosion of digital content have put fans closer than ever to the athletes they idolize. For the players, it means a direct pipeline to consumers and the ability to capitalize on their personal brand in a way the obligatory endorsement deal never could. Meanwhile Hollywood, long a moonlighting destination for athletes, is no longer satisfied to watch from the sidelines, as evidenced by WME's $2.45 billion deal last year for sports agency IMG, creating a behemoth with tentacles in every facet of the media industry.

And so the timing would appear to be right for something like TPT. "Derek had this vision for creating a company that leverages technology to bring athletes closer to fans," says Jon Sakoda, managing partner at Silicon Valley venture capital firm NEA, who first met Jeter in October at a Goldman Sachs technology and Internet conference in Las Vegas. "Athletes are looking for a trusted platform they could work with to tell their stories. He clearly tapped a nerve."

In June, NEA announced $9.5 million in Series B funding for TPT, marking its first round of venture capital funding. Original investors Legendary Entertainment and its CEO, Thomas Tull — an avowed Yankees fan and an owner of the Pittsburgh Steelers — have contributed about $7 million. "He described to me a forum where athletes would have multiple reach points to speak directly to fans. Unfiltered. And I literally said to him, 'I'm not sure exactly what the business plan is, but if you can pull this off, it will be very interesting,' " says Tull. "And we wrote the check."

And Jeter — whose career salary with the Yankees amounted to $269 million — also has put his own money into the venture, though (in classic form) he won't reveal how much.

Few athletes are as well positioned as Jeter to craft a second career off the field. Endorsements still are the easy money for athletes, and Jeter's unimpeachable brand made him the top-grossing endorser in baseball, with $130 million in career earnings through deals with Nike, Gatorade, Movado and others. And while many of his peers have failed to craft post-playing careers, Jeter had a plan. "I didn't want to wake up one day and say, 'What am I going to do now?' " he says.

The attributes fueling Jeter's entrepreneurial projects — his focus, optimism, work ethic — served him well during his playing days. "In baseball and in life, it's about how consistent you are. And his consistency level is off the charts," says Casey Close, who has been Jeter's agent since 1993.

He approached the game with "a blue-collar mentality," notes Joe Torre, the Yankees manager from Jeter's rookie season in 1996 until 2007. He would struggle to give his shortstop a day off, and even a slump could not send Jeter to the bench.

One such slump dogged Jeter in April 2004, when he was stuck in a 0-for-32 skid, the longest of his career. "He couldn't buy a hit," recalls Torre. "I'll never forget this: We were in Baltimore, there was a runner at second and there were two out. Now any time there's two out and there's a runner on base, you're not going to bunt. You're going to knock the run in. So he tries to bunt and he's thrown out at first."

When Jeter returned to the dugout, his incredulous manager demanded an explanation. "I said, 'What the hell are you doing?!' And he said, 'I needed a hit, Mr. T. I needed a hit.' And you couldn't help but laugh because he's just so honest. It was just desperate straits. And even during that time, I said, 'Derek, let me sit you for a day. Why don't you take a day off?' He wanted no part of it. He wasn't going to break out of a slump on the bench. So he always looked it in the eye. You couldn't help but admire it."

By the end of his career, Jeter was the Yankees' all-time leader in games (2,747), at-bats (11,195), hits (3,465, sixth most in history), doubles (544) and stolen bases (358).

On Sept. 29, Jeter played his final game at Fenway Park, home of the arch-rival Boston Red Sox. He was honored with a pregame ceremony that included on-field congratulations from Boston sports greats (Carl Yastrzemski, Bobby Orr, former New England Patriot Troy Brown and erstwhile Celtics forward Pierce). But the highlight might have occurred when Jeter left the field after his final career at-bat, as he received a prolonged standing ovation from the Boston faithful. Throughout Jeter's final season, similar scenarios played out at ballparks across the country. He was presented with gifts in every city the Yankees visited, while opposing players stood at the top of their dugouts and applauded.

It's that mass appeal and the ability to transcend rivalries as a sort of sports god emeritus that make his plans for TPT seem like a potential game changer. TPT was hatched in 2013 by Jeter and Jaymee Messler, the then-chief marketing officer of Jeter's agency Excel Sports Management and current president of TPT. Jeter was sitting out the postseason, having aggravated a devastating 2012 ankle injury sustained during the first game of the American League Championship Series. They had an idea to build a new media company that would leverage Jeter's trusted brand and capitalize on Messler's deep contacts among athletes. (She was one of the original employees at New York-based Excel, having arrived there with Jeff Schwartz, who started the agency in 2002 when he left Michael Ovitz's AMG.)

Around the same time, in November 2013, Simon & Schuster announced Jeter Publishing and Jeter Children's imprints. The first book — The Contract, a middle-grade reader inspired by his youth as a Little League striver and co-written with noted kids author Paul Mantell — debuted last fall to moderately healthy sales. So far there have been more than half a dozen books, including a just-released autobiography by Patriots tight end Rob Gronkowski and Seeing Home: The Ed Lucas Story, about a blind sportswriter, which has been optioned by Hollywood producer Elliot Abbott (Awakenings, A League of Their Own).

The imprint grew out of Jeter's interest in content, he says. "I'm interested in people's stories, in how they made it. I think a lot of times people assume you're successful overnight. But I like to hear about all the speed bumps that you've encountered along the way." (It's why a recent favorite was Andre Agassi's unvarnished autobiography Open; "I didn't know any of that stuff," says Jeter.)

And TPT would be another way to tell stories. Their goal was to have the site up and running by the time Jeter retired. And on Oct. 1, two days after Jeter played his final game in the major leagues, TPT launched. The media reaction was predictable. "For the first six months, people would talk about us as a vanity site," recalls Messler.

But athletes jumped at the opportunity to own the narrative. Indeed, when Woods and his agent Mark Steinberg, a partner at Excel, wanted to refute the Jenkins piece — which ran in Golf Digest complete with photos of a Woods look-alike posed in front of a Cadillac Escalade — they reached out to TPT. And many of the athletes on the company's board, including Kevin Love, Pierce and Patrick, are Excel clients, which early on fueled the perception that TPT was some sort of in-house PR vehicle. Messler stresses that the site is "agency agnostic," though she admits that educating the agent world has been "a process." And she notes that only about 20 percent of the athletes who have contributed to the site are Excel clients.

Nearly 300 athletes have supplied more than 600 written pieces, podcasts or video interviews. The site has averaged 1.1 million unique viewers each month from January through June, according to Google analytics, while July is tracking to be TPT's best month yet with 2 million uniques. Those are hardly home-run numbers (top sports site ESPN pulled in 72.4 million uniques in June), but the site has an average time on page of five minutes, more than double the media standard. TPT also is making news and increasingly being cited by the mainstream sports press, as when Love announced July 1 that he would return to the Cleveland Cavaliers in a five-year, $110 million deal or when DeAndre Jordan explained in a July 21 piece why he backed out of a verbal commitment to the Dallas Mavericks and instead re-signed with the Clippers. "I thought [free agency] was going to be fun," wrote Jordan. "I thought it was going to be like when I got recruited during college. But as it turns out, deciding what your future is going to be like is mostly a headache."

Athletes work with editors to craft bylined pieces, which in most cases are culled from interviews; they get final approval over anything that goes on the site. Pieces are fact-checked, but potential land mines persist. Ortiz, the Red Sox designated hitter, has been under a cloud of suspicion since his name appeared on a list of MLB players who tested positive for steroids in 2003, before the league began mandatory drug testing. He has denied taking steroids, attributing the positive result to over-the-counter substances that were not then banned by baseball. "In some people's minds, I will always be considered a cheater. And that's bullshit," Ortiz wrote on the site. "Mark my words: Nobody in MLB history has been tested for PEDs more than me. You know how many times I've been tested since 2004? More than 80."

Editors attempted to fact-check Ortiz's assertions with Major League Baseball, but the league declined to comment. What if Ortiz is found to have taken steroids? "That's a tough one," admits Gary Hoenig, TPT's editorial director, while stressing that he stands behind the story. "If it happens, we'll deal with it. I don't know how we'll deal with it, but we'll ask him to make a statement."

Of course, athletes can talk directly to fans through Facebook and Twitter, but social media has proved a minefield for many celebrities, so having a team of editors available to distill and polish words is a big draw — even if someone else owns that content. (Athletes are not paid for their submissions, but some board members have equity.) And the site is getting them to discuss the kind of issues that they formerly would have only felt comfortable obliquely referencing in less controlled media avenues.

"Instead of going through a [reporter], you actually get to tweak it and make changes and really get to voice your truth," says Blake Griffin, who has penned several pieces for the site, including a revealing narrative about former Clippers owner Donald Sterling, whom he called a "known racist" who screamed at his players from the stands in a voice that "sounds like a combination of Walter Matthau and Michael Jackson."

And in keeping with the company's for-the-athlete mission, Jeter is recruiting retired players to join an advisory board that will aid athletes in the often-rocky transition out of the game. Michael Strahan, Billie Jean King, Jason Kidd and Mark Jackson are among those who have already committed.

TPT has distribution partnerships with AOL.com, which reaches 92 million uniques each month, and SiriusXM, which airs a weekly radio show hosted by Ben Lyons (who has worked with ESPN and is perhaps best known for his brief stint as Roger Ebert's replacement on At the Movies). On July 29, the company launched TPT Assist, a platform in which athletes can pro­mote their charities. And it is exploring producing content such as documentaries for traditional media outlets. TPT also is seeking to distribute sports-related films, possibly through the Legendary partnership. Right now, the small, Manhattan-based staff of roughly 20 editors and producers puts up about six pieces of content each day. The site has lined up sponsorships; for instance, Dove sponsored a series about March Madness. Industry observers suggest that a partnership with an established vertical is the key to growth. But Messler notes that the company is "not rushing to do any kind of big partnership."

Jeter stays out of the day-to-day editorial minutiae, though he was in the trenches when TPT was in the beta stage, proselytizing in meetings with athletes including Nash, Griffin, Andrew McCutchen and Russell Wilson. The Seattle Seahawks quarterback was among the first contributors with a piece about domestic violence that was posted last fall when the NFL was reeling from a spate of violent off-field incidents involving several players, including Adrian Peterson and former Baltimore Ravens running back Ray Rice. Asked if the site has been approached by athletes looking to publicly scrub their reputations, Jeter laughs ruefully. "No. Scrub their reputations? We want athletes to be open and honest."

The baseball world is awaiting a full-throated explanation from Jeter's former teammate Alex Rodriguez, who weathered an unprecedented 162-game suspension — the entire 2014 season — for doping and misleading investigators. Would Jeter ever pick up the phone and ask Rodriguez to contribute?

"No, I'm not going to start calling people like I'm a member of the media and say, 'Hey, I've got this idea for you.' I would not be comfortable doing that with anyone. I don't view myself as being a member of the media."

While playing, Jeter studiously avoided the media, which paid considerable attention to his dating life (he had relationships with Mariah Carey, Minka Kelly, Jessica Biel, Adriana Lima and Jordana Brewster and is now dating model Hannah Davis). "I was always scared that I'd see my name and then scroll to see what they're saying," he recalls. "And I didn't want to deal with that when I was playing. I'd tell my family and friends, 'If you read something or hear something, don't tell me about it.' I didn't want to read negativity."

Anyone who knows Jeter credits an upbringing where achievement and discipline were paramount. "We weren't allowed to come home with anything less than a B," says his sister, Sharlee, who is five years younger than Jeter. "My mom wasn't having it." His mother, Dorothy, worked as an accountant, while his father, Charles, was a drug and alcohol abuse counselor. And if there was the obligatory amount of sibling rivalry, loyalty trumped jealousy.

"We would argue a lot," says Sharlee, who also was an athlete in high school, playing volleyball and softball. "But if we couldn't stand each other inside the house, outside the house you better not say anything about either one of us. We were very protective of one another."

And Jeter's biracial heritage — his mother is white and his father is black — has only added to his appeal; he appears the embodiment of post-racial aspirations in an era that is decidedly not.

"Derek and I talk about this all the time," says Sharlee. "We believe we have the best of all worlds. It has exposed us to so many different things just within our family. We were raised in a house where you didn't have one group of friends. You didn't have all black friends, all white friends, all Spanish friends. You had good friends."

Jeter still consults his parents about the major decisions in his life. "They were always present, and they were always honest," says Jeter. "I think you need people in your life who are going to tell you when you're doing good, but more importantly, when you're doing wrong. I still lean on them today."

Sharlee runs the Turn 2 Foundation, which Derek started with the help of his father during his rookie year. Based in Manhattan, Turn 2 has awarded more than $20 million toward programs for young people in New York, Kalamazoo and Tampa, Fla. In June, the foundation partnered with the cyber-bullying app StopIt (which Jeter has personally invested in). "It aligned with what we were trying to do [at the foundation]," says Sharlee. "And it was something that Derek wanted to back financially because he thought it was an important issue."

Jeter now lives full-time in Tampa, where he recently has taken up golf; former teammates Tino Martinez and Gary Sheffield are frequent golfing partners. "I'm very bad," he says unconvincingly. Jeter checks in with Messler on most days and discusses ideas with editors via phone and text.

Messler has given up trying to convince Jeter to open a Twitter account. "I pick my battles," she sighs. But that doesn't mean the editorial team wouldn't like to see him contribute more to the site. "They're always pitching me ideas," Jeter says. One is to have him randomly show up at a corporate team softball game in Central Park, surprising the office drones suited up in their company T-shirts. Alas, admits Messler, "That's one idea that doesn't seem to be getting any momentum."

But in other ways, Jeter is embracing change. Today, less than a year after getting standing ovations in ballparks all across America, he sits in a second-floor event space at The Standard, making a surprising revelation: "I don't miss playing." But he admits that the feeling is "kind of strange" and allows that maybe in a few years he'll feel differently. He still has aspirations to own a team. "I want to be able to call the shots."

But right now he's enjoying the mundane activities that the rest of us take for granted. "I went to my grandparents' house. The last time I was there in the summer was when I was 11," he says. "And I had a barbecue at my house on the Fourth of July. First time ever."

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