Last Sunday, many people were shocked when it was announced that Serena Williams would be competing in the women’s singles at Wimbledon as a wild card – almost four years after her much-hyped retirement.
But tennis insiders say the move makes perfect sense. Gault, 44, is in great shape and, like many star players, is desperate for the spotlight he’s had for a long time.
“When you watch videos of her practice and watch her compete in doubles, she looks amazing,” Matthew Futterman, author of the upcoming book “The Cruelest Game: Chasing the Greatness of Professional Tennis” (Doubleday, Aug. 4), told Page Six. “Her service is great. She still has a lot of tennis in her hands.”
Futterman points out that Williams joins the ranks of stars in other sports, such as Michael Jordan and Tom Brady, who retired because they couldn’t step away from their favorite sport.
And while Williams has remained busy in recent years with a number of ventures in the entertainment and technology fields, Futterman said, “There is no business meeting or fashion shoot that can recreate the competitive thrill of elite sports with the whole world watching.” “Who wouldn’t want to experience it a few more times if they could?”
When Williams signed for 2022, she cited motherhood as a driving force. At that point, she only had one child, daughter Olympia, whom she gave birth to in 2017. She said her pregnancy was fairly uneventful, but she had to have an emergency C-section and later experienced life-threatening complications, but she was “lucky to survive.”
Around the time of her retirement, Williams expressed frustration at struggling to have it all, which perhaps foreshadowed the fact that she wasn’t able to make it on the court.
“I didn’t want to have to choose between tennis and my family. I don’t think it’s fair. If I were a man, I would have continued to compete and win while my wife did physical labor to grow our family, so I’m not writing this. I could have been more Tom Brady if I had the chance,” she told Vogue in August 2022.
When asked why he chose to return, Williams had a simple answer.
“Why not? Because I don’t have a better explanation,” she said earlier this month, just after it was revealed that she would be competing in doubles rather than 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) also appear to be a key motivator for her return.
“For me right now, it’s really just… getting the kids to watch me play,” Williams said in a press conference earlier this month.
Anonymous tennis sources told Page Six that young players are likely to be shaking in their sneakers when Williams returns to Wimbledon, which begins Monday.
“They’re probably pretty scared. They all know what she’s capable of,” top seeds Aryna Sabalenka, 28, Yelena Rybakina, 27, and others told Page Six of her tournament. “They all grew up watching her. They’re all in awe of her. Now she’s going to be back on the other side of the net. For them (and) others, they’ve never played against her before. It’s going to take some adjustment.”
Williams, who has won 23 Grand Slam titles, is believed to be in good mental health.
“She had nothing left to prove,” Futterman said. “She came back from all the big moments. She did it all. She won a Grand Slam while pregnant. She’s already like superwoman.”
In fact, Williams has been busy ever since he was thought to be retiring.
Through her venture capital firm Serena Ventures, she has invested in more than 80 companies in her portfolio, including MasterClass, workout company Tonal, and Ro Weight Loss, where she is a spokesperson and celebrity ambassador.
Following the huge success of the Academy Award-nominated biopic King Richard, she founded her own production company, Nine to Six Productions, in April 2023. The biopic tells the true story of their father and his mentoring of Venus and Serena in the public courts of Compton, California, until they achieved professional fame. Williams served as an executive producer on the film, starring Will Smith, along with sisters Venus and Isha Price.
In April 2024, Williams launched her own makeup brand, WYN Beauty. It’s a line of vegan, cruelty-free cosmetics in tennis ball-colored packaging designed for athletes and active consumers.
In May, she attended the Met Gala wearing a metallic Marc Jacobs minidress and gladiator heels to support Sister Venus, who was one of the co-chairs of the 2026 event along with Beyoncé, Nicole Kidman and Anna Wintour.
Earlier this year, she co-starred in the reality documentary series “The CEO Club,” which focuses on entrepreneurship.
“[She was]very excited to be a part of the show,” a production source told Page Six. “(She) was juggling kids, family life and being a working mother.”
But business and showbiz can’t match the thrill of being a sports superstar.
“There’s no question that she’s a great mother and a great businesswoman, but that doesn’t make her happy,” EAG Sports Management CEO Denise White told Page Six.
“Maybe there’s a little ego. There’s no way it can’t exist.” White added. “It’s 2% ego and 98% missing the sport.”
It’s difficult for big stars to build a life without pursuing sports.
“These athletes have been training on a schedule for 25, 30 years. Now you’re taking away their schedule, taking away their sport, their competitiveness, the excitement of competing. That’s their high,” White said.
But she could be like Tom Brady and tarnish her legacy with a clumsy comeback.
Tomljanovic at the US Open. Getty Images
In 2022, he announced his retirement after 22 seasons and six Super Bowl appearances with the New England Patriots.
And 40 days later, he announced he was joining the Tampa Bay Buccaneers, saying his “desire to compete” remained. He broke individual passing records in 2022-2023, but it was a rocky year for the Bucks, who finished with an 8-9 record — a strange footnote to a storied career.
Jordan wandered further. When he announced his retirement from the Chicago Bulls in 1993, he had won three straight NBA championships and was on top of his game. He kept playing – surprise! — Minor League Baseball against the Chicago White Sox.
He then returned to the Bulls in 1995 and led them to three more consecutive championships from 1996 to 1998. He retired again in early 1999 and returned to the NBA in 2003, playing two seasons with the Washington Wizards, but his success was far less productive than his multiple three-peats with the Bulls.
Career decisions like this show how difficult it is for superstar athletes to step off the stage, Futterman noted.
“Movie stars and pop stars can continue to perform and continue to receive the love and admiration of the public and the adrenaline rush of thousands of people rooting for them and truly caring about their efforts,” he said. “Athletes don’t have that choice.”
They can try to keep performing, he noted, but that’s much harder to do than, say, an aging rock star who continues touring into his 70s. And “eventually, your body won’t allow it.”
Williams’ longtime friend Dee Okrepo Hilfiger, who appeared with her on “The CEO Club,” said she was surprised by the news of her return.
“This is a very bold and brave move,” she told Page Six. “I hope she goes out and kills me.”
Futterman wasn’t surprised. He and others were watching closely for a comeback after Williams rejoined the mandatory anti-doping testing pool in December.
“There’s no reason to go through the humiliation of a drug test or report your whereabouts to authorities every day if you’re not going to play,” Futterman said. “When she left the court for the last time, she was very clear. Her main motivation was that she wanted another baby. She had the space to do that. It was a choice she had to make. And she’s done it and wants to do the things she loved and missed again.”
An anonymous insider agrees.
They said, “She has done it all. It shows that her first love is tennis. It always has been and always will be.”
