It is one of those odd-couple pairings that only seems to happen in Palm Beach or on a high-stakes Twitter feed. Donald Trump and Serena Williams have a history that stretches back long before he was in the White House and she was "evolving" away from tennis.
You’ve probably seen that surreal clip. It’s 2015. Trump is in a full suit, tie flapping, and—for some reason—he’s barefoot on a tennis court. He’s lobbing balls at Serena Williams. She’s humoring him, laughing, letting him look like he’s got a decent backhand. It looks like two old friends hanging out, which is exactly why people were so confused when her name popped up in a Manhattan courtroom years later.
The Spreadsheet That Shocked Tennis Fans
In early 2024, during Trump’s "hush money" trial, a former aide named Madeleine Westerhout took the stand. Prosecutors pulled up an Excel spreadsheet from January 2017—just days after the inauguration. It was a list of people Trump "frequently spoke to."
There, nestled among family members and political fixers, was Serena Williams.
The internet, naturally, lost its mind. Why was the greatest tennis player of all time on a "frequent contact" list for the President of the United States? Honestly, the answer is kind of boring, but the optics were wild. Serena has always been cagey about it. When the New York Times grilled her on the phone calls in June 2024, she got visibly testy.
"I talk to a lot of presidents," she told reporter David Marchese. "I spoke to Barack, I spoke to the Clintons. I spoke to every president since I’ve been alive, including Ronald Reagan."
She wasn't going to "go there." She didn't explain the frequency or the topics. She basically shut down the line of questioning, leaving everyone to wonder if they were talking about tax policy or just the weather in Florida.
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Neighbors and Barefoot Tennis
To understand Donald Trump and Serena Williams, you have to look at Palm Beach. They both lived there for years. In that world, the super-famous and the super-rich basically run into each other at the grocery store or Gucci cocktail parties (which they actually attended together in 2009).
The 2015 video mentioned earlier happened at the opening of the Trump National Golf Club’s tennis center in Sterling, Virginia. Trump called her the "greatest" and praised her Vogue cover. Serena, for her part, reportedly let him win a point during their volley.
It was a PR win for him and a standard celebrity appearance for her. But it set a narrative. When Trump ran for president later that year, the questions started coming. Would she endorse him?
The answer was a firm no, but not for the reasons you’d think.
The Religious Neutrality Factor
Serena is a devout Jehovah’s Witness. Because of her faith, she doesn’t vote. She doesn’t lobby. She doesn’t participate in the political process at all. This gave her a "get out of jail free" card when it came to choosing sides in 2016 or 2020. She didn't have to denounce him or support him; she just had to stay neutral.
Still, the world kept trying to link them.
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The $1 Million Offer and the "Battle of the Sexes"
One of the weirdest chapters in the Donald Trump and Serena Williams saga involves John McEnroe. Way back in the late 90s, when Serena and Venus were teenagers, Trump reportedly tried to stage a modern-day "Battle of the Sexes."
He offered McEnroe $1 million to play one of the sisters.
McEnroe turned it down. He said he didn't want to "mix apples and oranges." But Trump’s fascination with Serena’s dominance stayed consistent. Even after he became president, he’d tweet about her wins. In 2020, after she beat Jessica Pegula, he called her a "great player and an even greater person."
It’s a weirdly wholesome sentiment coming from a man who also lambasted Colin Kaepernick—someone Serena publicly supported.
When Things Got Awkward
It hasn't all been barefoot volleys and polite tweets. In 2018, a reporter at a press conference brought up comments Trump allegedly made to him in 2004. The reporter, Bill Simons, claimed Trump told him Serena lost to Maria Sharapova because she was "intimidated" by Sharapova’s looks.
Serena’s reaction? She handled it with a shrug and a "I never knew he said that."
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She has a knack for side-stepping the drama. Even when the world was burning over Trump’s policies, Serena kept her head down and her game up. She never used her platform to attack him, even when her close friends (like Meghan Markle) were much more vocal about their distaste for his administration.
The Reality of the Relationship
So, are they friends? Probably not in the "grabbing coffee" sense. They are two titans of their respective industries who shared a zip code and a mutual appreciation for being at the top.
Trump respects winners. Serena is the ultimate winner.
For Serena, Trump was likely just another powerful man in a long line of powerful men who wanted to be associated with her greatness. Whether it was Reagan, Obama, or Trump, she treated the office with a level of detached professionalism that is increasingly rare today.
Actionable Insights for the Curious
If you are trying to parse the truth from the tabloid noise regarding Donald Trump and Serena Williams, keep these three things in mind:
- Look at the Geography: Most of their interactions stem from the Palm Beach social circuit. Fame creates a very small bubble where billionaires and athletes are naturally forced into the same rooms.
- Understand the Faith: Serena's religious stance as a Jehovah's Witness is the primary reason she remains politically elusive. Any attempt to frame her as a "secret supporter" or a "closet hater" ignores her lifelong commitment to political neutrality.
- Contextualize the Calls: Being on a "most contacted" list in 2017 doesn't necessarily mean they were best friends. At the start of a presidency, moguls often reach out to icons for advice on sports initiatives, cultural optics, or simply to maintain a connection with a high-profile neighbor.
The barefoot tennis match in Virginia might have been a "puff piece," but it perfectly encapsulates their dynamic: a lot of performative friendliness, a bit of ego, and two people who know exactly how to stay in the spotlight.