Serena Williams, one of the most decorated tennis players in history with 23 Grand Slam singles titles, dominated the women’s game for more than two decades and in doing so cemented her legacy as herself as one of history’s greatest athletes.
Two years into retirement, Williams’s name has re-entered the news for her unlikely and intriguing relationship with former President Donald Trump.
The pair have been pictured together on numerous occasions, danced at parties and even once shared a tennis court.
Donald Trump and professional Tennis Player Serena Williams attend the Gucci cocktail party at Gucci Fifth Avenue on September 16, 2009 in New York City.
The surprising list of connections, and the athlete’s reticence when discussing Trump, has raised questions over the exact nature of the relationship between Tennis’s biggest star and the 45th commander-in-chief.
Are Donald Trump and Serena Williams Friends?
Speculations about Serena’s relationship with Trump emerged in May, when she became embroiled in the former president’s hush money trial.
During the proceedings, emails from 2017 between Trump’s former executive assistant Madeleine Westerhout and Trump Organization employee Rhona Graff were displayed to the court, containing a preliminary list of individuals whom Trump “frequently spoke to.”
Besides NFL quarterback Tom Brady, the most intriguing name in the rolodex was Williams, and questions immediately emerged about why the tennis star would be included alongside such figures as Michael Cohen and Bill O’Reilly in a list of Trump’s closest contacts.
What Did Williams Say About Trump?
A month later, during an interview on the New York Times podcast, Serena shirked a question about the pair’s relationship.
Asked whether she did “speak frequently” with Trump prior to his election, she said: “I mean, is this what this interview is about?”, before telling Marchese that speaking to those in the oval office was not uncommon for one of America’s top athletes.
“I talk to a lot of presidents,” Williams said. “I spoke to Barack, I spoke to the Clintons. I spoke to every president since I’ve been alive, including Ronald Reagan, I’ll have you know.”
When pressed again, Williams insisted that she was “not going to go there.”
Newsweek reached out to Serena Williams’s management agency, William Morris Endeavor Entertainment, for comment.
Have the Pair Met Before?
The pair, who both reside in Palm Beach, Florida, have famously crossed paths a number of times.
Williams hit the ceremonial first serve to Trump at the opening of the Trump National Golf Club in 2015, only months before he announced his candidacy for the 2016 presidential election.
Williams, then-world number one, allowed the real estate mogul to win a point against her after he missed his first volley return.
She was also pictured with Melania Trump at a New Year’s eve party hosted by the couple and, according to S.L. Price’s 2015 profile of the athlete for Sports Illustrated, even danced with the soon-to-be president.
“Everyone in Palm Beach kind of know[s] each other,” Williams said, when asked about her encounters with Trump in 2016, and whether the pair could be described as anything closer than acquaintances, albeit frequent ones, remains in doubt.
His attempt to involve her in a recreation of the famed “battle of the sexes” tennis match in 2000 also raises questions over how much he respects the athlete.
During a 2018 interview with Graham Bensinger, John McEnroe, another of Tennis’s most recognizable figures, claimed that Trump had offered him $1 million dollars to face off against either of the Williams sisters.
“I was calling a match and suddenly I get this envelope, and it’s from Donald Trump, who is promoter galore,” McEnroe said. “So he wrote me a letter, it went, ‘Dear John, I want to offer you $1 million to play either Serena or Venus.'”
The events, which were reported at the time by the New York Times, came after the then-41-year-old McEnroe had said that any male college player would be able to beat the sisters in a match.
Does Williams Support Trump’s Campaign?
“I don’t get involved in politics. I don’t vote,” Williams told reporters when asked about the Republican nominee in June 2016. “It goes back to my religion, and I’m not involved at all in that political scene.”
Like their mother, the Williams sisters are practicing Jehovah’s Witnesses, a denomination which prohibits running for political office, voicing support for a particular candidate and even voting.
Even if the pair are close, therefore, it is unlikely the extent of Williams support for Donald Trump will ever be revealed by the athlete herself.
