Naomi Osaka Is Challenging Convention and Charting a New Course

While her tennis is on pause, the 25-year-old has proven that she can still be competitive and stay connected to sport through her various off-court pursuits.

The August 2023 issue of Sports Illustrated features The Power List, the definitive index of the 50 most influential figures and forces who drive the sports world, on and off the field and court. For more on The Power List’s Athletes, like Naomi Osaka, click here.

It was the summer of 2020, and veteran tennis journalist Ben Rothenberg seized on a thought. Naomi Osaka would make for a hell of a biography. Then 22, Osaka was emerging as a singularly beguiling figure, the personification of a globalized, multicultural, digital, complicated world.

Here was Osaka, both accessible to her millions of online followers and inscrutable, as she cast her eyes downward and (by her own admission) mumbled through interviews. She was fiercely confident but also strikingly vulnerable. She was born to a Japanese mother and Haitian father but grew up mostly in Florida and was unmistakably American, not least in her slang and diction. She was a celebrity whose tennis earnings were dwarfed by her endorsement income—her sponsors so plentiful that Nike had to relax its rules and let other brands put their patches on her tennis attire. Yet, for all the photo ops and appearances at the Met Gala, Osaka was just as happy to sit in the stands with other millennials at Overwatch tournaments in Brooklyn or the USC spring game in L.A. in April. She might characterize herself as “super-shy,” but there she was, on the streets of Minneapolis, attending a protest after the murder of George Floyd by police.

What really got Rothenberg thinking about Osaka’s book potential: That summer, playing in the Western & Southern Open, Osaka was shaken by the shooting of Jacob Blake, a 29-year-old Black man police fired on in Wisconsin. Tennis seemed so trivial by comparison, and Osaka declined to play her scheduled semifinal match. Rather than default her, the tournament took the unprecedented step of halting all play, a testament to both Osaka’s star power and her moral force. A few weeks later, Osaka won the U.S. Open, marking the third major title of her career, all but consecrating her eventual entrance into the sport’s Hall of Fame. A few months after that, Osaka brought her power, athleticism and fearlessness to bear and won the 2021 Australian Open, looking for all the world like the heir apparent to Serena Williams, a dominating, generational star transcending sports.

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Rothenberg figured, rightly, that he had timed it all awfully well. And then Osaka’s story began whipsawing like a mechanical bull. That 2021 Australian Open held two and a half years ago? It would mark Osaka’s last—and, who knows, potentially final?—tennis title. That spring, before the French Open in Paris, Osaka announced she would not attend mandated press conferences, as those sessions were at odds with her mental health. Amid controversies and threats of fines, she played one match and then withdrew from the event.

As defending champ, she lost tearfully at the U.S. Open. By the end of the year, she had fallen out of the top 10 in the WTA rankings. By the end of 2022—in which she played sporadically and won barely half the time—she had fallen out of the top 40. By that time, she had announced that she and her longtime boyfriend, the rapper Cordae, were expecting a child and she would be playing no tennis in ’23.

There was a time not long ago when an athlete’s relevance and income moved in more or less direct proportion to their playing results. The rules of the road were simple. Winning brings opportunities (and triggers bonus clauses and beckons biographies). Fail to win, and opportunities dry up. Stop playing entirely, and the gravy train moves on. Beyond that, an athlete speaking openly about their social anxiety and mental health challenges might as well be radioactive to marketers. How can you represent a brand if you’re not willing to be front-facing?

And yet Osaka the pathbreaker—on brand as ever; forgive the pun—has taken this conventional wisdom and batted it back with great force. Her lack of tennis has not dented her earning potential at all. Quite the contrary. Osaka Inc. is as strong as ever. Her list of sponsors, partnerships and investments—too numerous to chronicle fully here—now includes more than 20 brands, from Nike, Victoria’s Secret and Beats to jeans and vegan ramen. For the third straight year, she was the world’s top-earning female athlete, making an estimated $50 million annually from off-court pursuits.

In keeping with the times, Osaka knows that the real contemporary power is not wealth but influence. So it is, she is not simply slapping her name, image and likeness on brands, but is also often involved in product designs and marketing campaigns. And she is spreading her gospel. She has her own media production company, Hana Kuma. She finds investments that are consistent with her values, not least her partial ownership of the NWSL’s North Carolina Courage. In 2022 she divorced IMG, the management giant that signed her as a teenager, and didn’t decamp to a rival agency, but, rather, founded her own agency, Evolve. As she said at the time of launch, “Evolve represents the evolution of not just my business career, but also the way athletes can control their destiny.”

Not all of her self-controlled destiny has been a success. As part of a deal with FTX, Osaka received equity and compensation in the form of crypto. When FTX collapsed spectacularly last year, she was left holding worthless digital currency and was among the celebrity endorsers named in an $11 billion class-action lawsuit. She has taken equity stakes in companies that have yet to find traction. And critics are within their rights to wonder whether all of this (over?) extension is a symptom or cause of her stalled tennis career. In 2022, Osaka parted ways with coaches and trainers who wondered quietly why they were more motivated than the world-class athlete employing them.

Rothenberg, the journalist, has watched it all play out in real time. If his book morphs into something altogether different from a straightforward portrait of an athlete in full bloom, it may ultimately end up as something more interesting. Among his observations: “Naomi’s competitiveness has been a constant since childhood, and I think she’s channeled a way to scratch that itch through her off-court ventures as well. She can score wins in lots of different ways outside of tennis, whether it’s landing a magazine cover, being named a Met Gala host or having a clothing collection launch. And there are definitely perceptible rankings to measure her off-court business success. . . . I think those sorts of challenges are as appealing to her, if not more so, than the actual money she’s raking in.”

That is, Osaka contains multitudes. And she is adamant that her interests and influence can coexist with her tennis. On July 12, she became a mother to a baby girl, and she has targeted the 2024 Australian Open as her return date. The tournament starts the same week as the publication of Rothenberg’s book, Naomi Osaka: Her Journey to Finding Her Power and Her Voice.