Add Page Six on Google Last Sunday, when it was announced that Serena Williams would be competing in the ladies’ singles at Wimbledon via a wild card — nearly four years after she retired to much fanfare — many were shocked.
But those in-the-know in the tennis world say the move makes perfect sense: The 44-year-old GOAT is in great condition and, like many star athletes, craves the spotlight she had for so long.
“Having seen videos of her practicing, seeing her competing in doubles, she looks great,” Matthew Futterman, author of the forthcoming book “The Cruelest Game: Chasing Greatness in Professional Tennis” (Doubleday, Aug. 4), told Page Six. “She’s serving great. She still has a lot of tennis in her hands.”
Futterman notes that Williams joins the rank of stars in other sports — like Michael Jordan and Tom Brady — who have retired only to not be able to stay away from the sport they excelled in.
And, while Williams has kept busy in recent years with a number of ventures in entertainment and tech, “there is no business meeting or fashion shoot that can replicate the thrill of competition in elite sport when the whole world is watching,” Futterman said. “Who wouldn’t want to try to experience that a few more times if they could?”
When Williams signed off in 2022, she cited motherhood as a driving factor. At that point, she had only one child, daughter Olympia, whom she gave birth to in 2017. After a fairly smooth pregnancy, she had to have an emergency C-section and endured life-threatening complications in its wake that she said she “was lucky to survive.”
Around the time of her retirement, Williams expressed frustration at struggling to have it all — perhaps foreshadowing the fact that she wasn’t done on the court.
“I never wanted to have to choose between tennis and a family. I don’t think it’s fair. If I were a guy, I wouldn’t be writing this because I’d be out there playing and winning while my wife was doing the physical labor of expanding our family. Maybe I’d be more of a Tom Brady if I had the opportunity,” she told Vogue in August 2022.
When addressing why she chose to come back, Williams gave a simple answer.
“Why not? For lack of a better explanation,” she said earlier this month, when it had only been revealed that she would be competing in doubles, not singles.
And, while she initially retired for family reasons, her daughters — she and her husband, Reddit co-founder Alexis Ohanian, welcomed their second child, daughter Adira, in 2023 — would also seem to be a key motivation for coming back.
“For me right now, it’s really just about … my kids getting to see me play,” Williams said at a press conference earlier this month.
An anonymous tennis insider told Page Six that Williams’ return to Wimbledon, which starts Monday, likely has younger players shaking in their sneakers.
“They’re probably pretty scared — they all know what she’s capable of,” they told Page Six of her competition, like top seeds Aryna Sabalenka, 28, and Elena Rybakina, 27. “They all grew up watching her; in awe of her. Now, she’s going to be back on the other side of the net. For them, [and] for others, they never faced her before — that takes some adjustment.”
Williams, who has won a whopping 23 Grand Slam titles, is also likely to be in a good place mentally.
“She had nothing left to prove,” Futterman said. “She’s come back from all the pivotal moments — she’s done everything. She won a Grand Slam while pregnant. She’s kind of Superwoman already.”
Indeed, Williams has kept plenty busy since her supposed retirement.
Via her venture capital firm, Serena Ventures, she’s invested in more than 80 companies in her portfolio, including MasterClass, workout company Tonal and Ro Weight Loss, for which she serves as spokesperson and celebrity ambassador.
In April 2023, she started her own production company, Nine Two Six Productions, following the mega success of the Oscar-nominated biopic “King Richard,” which told the true story of her father and his coaching Venus and Serena from the public courts in Compton, Calif., to pro fame. Williams, along with sisters Venus and Isha Price, was an executive producer on the film, which starred Will Smith.
In April 2024, Williams launched her makeup brand WYN Beauty, a line of vegan, cruelty-free cosmetics designed for athletes and active consumers in tennis ball-colored packaging.
This past May, she attended the Met Gala, wearing a metallic Marc Jacobs minidress with gladiator heels, to support sister Venus, who served as one of the co-chairs of the 2026 event alongside Beyoncé, Nicole Kidman and Anna Wintour.
Earlier this year she co-starred in “The CEO Club,” a reality docuseries focusing on entrepreneurship
“[She] was super excited to be part of the show,” a source close to the production told Page Six. “[Even though she was] juggling the kids, home life, being a working mom.”
But business and show biz can’t compete with the thrills of athletic superstardom.
“I’m sure she’s a fabulous mom, and a fabulous businesswoman. That’s still not going to fill her cup up,” Denise White, CEO of EAG Sports Management, told Page Six.
“Maybe there’s a little ego — how could there not be?” White added. “It’s 2% ego and 98% missing the sport.”
For mega stars, it’s hard to forge a life without athletic pursuits.
“These athletes have had schedules and have trained for 25 years, for 30 years, now you take away their schedule, you take away their sport, their competitiveness, the excitement to compete — that’s a high they have,” White said.
But there is the potential she could tarnish her legacy with an awkward return — à la Tom Brady.
In 2022, after 22 seasons and six Super Bowl rings with the New England Patriots, he announced he was retiring.
Then, after 40 days, he said his “appetite to compete” wasn’t gone and announced he was joining the Tampa Bay Buccaneers. While he broke individual passing records during the 2022-2023 season, it was a rocky year with the Bucs finishing with an 8-9 record — a strange footnote to a storied career.
Jordan took an even more wandering path. When he announced his retirement from the Chicago Bulls in 1993, he was going out on top, after having won three consecutive NBA championships. He went on to play — surprise! — minor league baseball with the Chicago White Sox.
Then, in 1995, he returned to the Bulls, leading them to win another three consecutive championships between 1996 and 1998. He retired again in early 1999, then returned to the NBA in 2003 to play for the Washington Wizards for two season that were far less successful than his multiple three-peats with the Bulls.
Such career decisions illustrate just how hard it is for superstar athletes to exit the stage, Futterman noted.
“Movie stars and pop stars can continue to perform and continue to receive the public love and adulation and the adrenaline rush of thousands of people cheering for them, and really caring about their endeavors,” he said. “Athletes don’t have that choice.”
They can try to keep playing, he noted, but doing so is far more difficult than, say, an aging rock star who keeps touring well into their 70s. And “eventually, their bodies don’t allow it.”
Dee Ocleppo Hilfiger, a long time friend of Williams, who starred on “The CEO Club” with her, said she was surprised by the news oof her return.
“It’s a very bold and brave move,” she told Page Six. “I hope she goes out and kills it.”
Futterman, for one, wasn’t surprised. He and others watching closely saw the comeback coming after Williams re-entered the required anti-doping test pool in December.
“There’s no reason why you would go through the indignities of drug testing, file your whereabouts with the authorities every day, if you aren’t going to play,” Futterman said. “She was very clear when she left the court last time. Her main motivation was, she wanted to have another baby. There was a window where she was going to do that. That was a choice she had to make, and she’s done that and wants to do what she loves and misses again.”
They said, “She’s done it all. It shows that her first love is tennis. It always was and it always will be.”
