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Pressing Forward: David Stern Is Not Looking Back

Nearly five years after stepping down (he did not retire) as NBA commissioner, David Stern remains as determined as ever. The reticent icon is busy crafting a second act that could impact the future of the game.

"Ask me anything,” David Stern says.

It's a Wednesday morning in August. We're sitting in his new office, 33 floors above Fifth Avenue and five blocks from his old office. Outside, it's so hot that the thermostat has been locked at 78 degrees to conserve energy. In here, however, Stern—76 years old, shirt creased, white hair still parted as if by laser—is unperturbed. If anything, he appears to be in a great mood.

Ask him anything? Where to start? In 30 years as NBA commissioner, Stern led a floundering league to unprecedented growth. Since his departure LeBron moved back to Cleveland, the Warriors became The Warriors, Donald Sterling got the boot, and LeBron left Cleveland again. And this is not even touching on the larger cultural shifts; remember, a year ago, when Mark Cuban was seriously considering running for President?

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Anything? How about what Stern has learned? What he misses? Why didn't he trade CP3 to the Lakers? Is that really the Larry O'Brien trophy over there on the shelf? Did he just give me a printed itinerary for our day? Does he always eat peanut butter cookies for breakfast? Does this mean I can eat peanut butter cookies for breakfast?

Or how about the deeper stuff: about family and motivation, what drove him to work 14-hour days and demand his staff do the same, and what drives him to keep showing up at the office from 10 to 7? Can he turn that stuff on and off or is he on some workaholic autopilot, a virtue that doubles as a flaw, forever keeping him from really pondering the why of life.

Then again, maybe I'm overthinking this. Stern only said to ask anything. He didn't say he'd answer. Because when has David Stern ever divulged anything he didn't want to divulge?

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His was a triumphant, carefully choreographed exit. On Feb. 1, 2014, after a nice round anniversary, Stern handed the job to his hand-picked successor, Adam Silver. Six months later Stern was inducted into the Hall of Fame.

What Stern didn't do, in any way, shape or form, was retire. "He hates when people say that," says Silver. No, Stern will explain with exasperation, as if you are a third-grader who forgot his homework yet again, all he did was step down. And just so we're clear: He did so on his terms. Because retiring is something old people do. Boring people. People unlike David Stern.

Even so, you could be forgiven for assuming that he had. In the half decade since, Stern has mostly dropped out of public view. No memoir to burnish his legacy—despite what he describes as "many, many" entreaties from literary agents. ("Too self-important," he explains. "Just thinking about it gives me a rash!") Stern agrees to infrequent interviews, which are usually brief or esoteric. (He was a guest on the first and only podcast of freelance writer Nunyo Demasio; he spoke to former NBA player Al Harrington for a video series on medical marijuana, which Stern supports.) Occasionally, he shares anecdotes—how he once beat Donald Trump at doubles tennis, for example—but rarely does he go into detail because, he says, "I don't do war stories." On the contrary, he's made an effort to limit his exposure. Upon hearing that his Q&A at Seton Hall in April with former players association head Charlie Grantham is now on YouTube, he says, "Was that recorded? Oh s---." The reason for this reticence, Stern says, is that, "There can be only one commissioner."

And the 56-year-old Silver has thrived in the position. He is markedly different from his mentor: forthcoming, a bit goofy, sensitive—even vulnerable. Whereas Stern often played the role of emperor, forever beating back the barbarians at the gate (the media and players union), Silver comes across more like a friend or an ally. One of his first acts was to drop the hammer on Sterling, the racist, sexist owner of the Clippers, who was banned from the NBA for life and forced to sell his team. Silver is open to feedback, encourages his players to speak out. He is a woke commissioner for a woke age.

This is not to diminish Stern's cultural legacy. He was ahead of the curve on many social issues. Met with Mandela. In 1992, on live TV at the All-Star Game, he hugged Magic Johnson—his favorite player ever—to demonstrate that HIV wasn't casually contagious. He arranged for a climate-change expert to appear at the owners' meetings way back in 2006. He pushed for African-American owners in his league at a time when the big four sports had none.

To this day Stern remains a staunch liberal, donating even if, as he puts it, "The Democratic Party has not been a successful investment." Still, he has plenty of ideas. He hated Hillary Clinton's "Stronger Together" and "I'm With Her" campaign slogans (too narrow, unlike, say, "Prosperity, Strength, Inclusiveness and Education," which Stern offers). And he is horrified by his former doubles opponent. "How dare he rip the fabric of the republic asunder for narrow partisan gains," Stern says of Trump. "It's not fair."

He does what he can, regularly speaking with Democratic figures he'd rather I not name. Dianne, his wife of 55 years, is on the board of Earthjustice, an organization that provides legal aid for environmental causes. Even so, Stern feels he has more to add to the Democrats but, "They don't ask and they don't value [the advice]." Friends lobbied him to run for mayor of New York City. He was also mentioned as a possible ambassador. Neither job was for him, though.

His passion lies elsewhere.

"You don't want to write about me," Stern said back in June. I had been trying to reach him since January. "My life is boring. Stultifying."

Plus, he didn't want me following him to his business meetings, as I'd proposed. What would the investors think? No, that would not do. Besides, Stern was so, so busy—the engagements and advisories and consultancies and investments and, oh hell, maybe it wouldn't be that bad for someone to witness it after all. Maybe he could even teach a reporter a thing or two. We set a date.

But then, in the interim, he talked himself out of it. On second thought, the idea struck him as "ridiculous" and "stupid." Still, he felt guilty about backing out. "I'll do my penance," he said. He offered a new scenario: lunch and an interview at his office.

For a high-profile figure, Stern has managed to keep much of his life private. His father, William, was a passionate, demanding man who put his life into the family business, Stern's Deli, on 23rd Street and Eighth Avenue in Manhattan. Stern's was open seven days a week, and until 1 a.m. on Saturday nights. David's mother, Anna, the ballast in the family, was the bookkeeper. David and his two sisters worked weekend shifts.

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William passed away in 1980, at 62, but his work ethic imprinted. David excelled at Teaneck (N.J.) High, then at Rutgers and Columbia Law School. He began representing the NBA in court cases in '67 while at Proskauer, Rose, Goetz & Mendelsohn, worked on the ABA-NBA merger in '76, then left to become the NBA's first general counsel, later ascending to executive VP. The league was struggling: 16 of the 23 teams lost money in '80–81, and an '82 Los Angeles Times story reported that up to 75% of the players were on drugs.

By the time Stern became commissioner, in 1984, he'd long since lost the battle for work-life balance. He and Dianne had two sons, Eric and Andrew. Once, Stern had coached both their basketball teams. Now he went "all in," as he likes to say, working as long as it took to get things right, which was often very, very long. Surrounding himself with young, ambitious people, Stern instilled a culture of near manic productivity. He'd later be described as "abrasive" (Rod Thorn) and "a yeller" (Steve Mills), but no one questioned Stern's effectiveness. He also countered his demanding, berating nature with a heavy dose of mentorship.

By the time Sports Illustrated printed the first (and, best I can tell, only) lengthy profile of Stern, in 1991, the league was ascendant and he had been rewarded with a five-year, $37.5 million contract. Stern was also adamant that the writer, E.M. Swift, not talk to his family. Neither did Stern provide much biographical information. (Swift was the second SI writer to try to tackle the subject after the first gave up.) Swift did procure one anonymous insight, though: "I think David has a fair amount of regret over his personal life. I understand that he is the same kind of father that he is a commissioner, and I don't think the kids have responded well to that. He can be so demanding, so much the perfectionist. It's also been really hard on David. He spends every waking hour thinking of the league. He expresses regret at times for who he is. He'll say, 'I terrorize, I demand so much from everyone. I can't back off. I can't pull down.' David only knows one way to go, and that's full speed ahead."

These days, Stern says he sees his sons regularly. Both went to law school in New York City. Eric, 50, works as the senior adviser to Montana governor Steve Bullock and lives in Helena. Andrew, 52, lives in New York City and is in real estate. Both are unmarried, and the Sterns have no grandchildren. Neither son tried to follow David into the NBA life. I'd offer further perspective, but they don't speak to the media. In Eric's case, he initially wrote that he'd be "happy to talk," but upon learning that his father didn't want him to, he went silent.

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Stern has long had a complicated relationship with the media. He tells me he once got a writer fired from USA Today because he wrote "the most horrible things about some of our people." Recalls Stern, "He said, 'You got me fired didn't you?' And I said, 'Yes, and I'm proud of it. I'd do it again.' There is a family. We call it the NBA family and we really, we live it."

Stern also recounts how in 2010 he fined Pistons general manager Joe Dumars $500,000 for leaking league memos to reporter Adrian Wojnarowski after enacting a sting. When Stern stepped down, Woj opened fire with both barrels, calling him, "the biggest ego in the history of the sport" among other things. ("I never read it but I heard it was nasty," Stern says.)

Still, Stern says he never disliked the media, that he understood they had a job to do. (As for his claim that he never read stories about himself, one longtime coworker says with a laugh, "Oh, he totally reads them.") "Bob Costas used to relish getting me on during the Finals," Stern smiles. "O.K., Bob, give me your best shot. It was kind of fun. If you stood on your hind legs and had federal judges dismissing your arguments and you've been commissioner for 30 years is there something new and different that's going to be thrown at you? Probably not." The real danger, Stern contends, is if you don't engage in the p.r. fray. "Hinkie's biggest mistake," he says when I bring up the former GM of the 76ers, Sam Hinkie. "He wouldn't talk to the media. What was that about?"

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This is how Stern viewed his job: as bodyguard for the league. He refers to the NBA as "an asset" and his goal was to "make the asset more valuable." He says, "When I think back on the best stuff, I'm not thinking about Michael hitting all the threes or the last shot. I think about Magic announcing he was HIV positive, and Latrell Sprewell deciding to choke P.J. Carlesimo, Ron Artest going into the stands, [former referee Tim] Donaghy betting on games. Those were places I had to step up and protect the league and that comes with the job. That wasn't extra stress. That was the job."

This trait both made Stern effective and difficult. "It's not always fun to be on the receiving end of it, but he gives you his views unfiltered," says Silver, who worked under Stern for 22 years and considers Stern "a friend and mentor." "My shorthand for his technique is pay attention. He pays attention to every detail. If he called a colleague and he didn't like the way the phone was answered by them or someone on their behalf, he let them know. And if he didn't think your outgoing voicemail message on your cellphone was an effective form of communication, he let you know."

Silver continues. "I learned that from him. We were alike. I'd react to all those small details before I worked for him, but always in my head. I never thought those were things you could actually talk to people about, and maybe I have a different way of talking to people about them, but I think that's always been our commonality. I've become more direct, and I've learned to become more assertive because of him." Silver pauses. "I learned from David that being direct with people is in their interest, not just our interest."

Direct is one way to put it.

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"Hey, listen s---foot, how about letting them know what you're doing before we walk in there?"

This is two hours into my morning with Stern and he's in a glass-walled conference room, speaking to and about a business partner.

As usual, he'd arrived that morning around 9:30 a.m., by car service from the home he and Dianne have owned for 40 years in Scarsdale. Outside his office, as always, is Linda Tosi, his assistant of 27 years. Working for Stern is one of two jobs she's had in her life and she says she loves it, even if it's more demanding now. At the NBA, Stern had three assistants; these days it's just Tosi. She has seen a lot. She also knows her job is to recede into the background. She'd prefer not to speak on the record. Or, really, to be part of the story at all. But if anyone should write a book, it's Tosi. But she won't. She will offer up that he's mellowed. "Did you know him before?" she asks. Also, she says, he can't stop working: "His motto was always 'a relentless pursuit of perfection' and that's entirely the case."

Most weeks Stern spends his Monday at Greycroft, the New York City venture capital firm where he is a senior adviser. Fridays he tries to take off. The majority of the time, though, he works in his spacious office, which has the feel of an extremely well-lit museum. His desk is meticulously organized; pencils separated from pens, an NBA-branded memo pad, a ripped-out newspaper story on top of stacked folders. (Stern, who prefers news to books, pores over three papers in print each day.) The other available spaces are filled with photos of Stern alongside various important folks: Mandela, Bill Clinton, Phil Jackson, Magic, Ronald Reagan. His Columbia law degree hangs on one wall. On another is a Sacramento Bee comic strip depicting him as Superman, printed after he worked to keep the Kings in town in 2013.