One of The People on Donald Trump’s Frequently Contacted List Has Us Utterly Shocked

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On Thursday, tennis phenom Serena Williams became involved, if tangentially, in Donald Trump’s ongoing “hush money” trial, when her name appeared on a 2017 list of people that Trump allegedly “frequently spoke to.” While this Excel spreadsheet of celebrities and bigwigs, formulated days after Trump was inaugurated in early 2017, by a longtime Trump Organization employee, mainly includes known Trump shoulder-brushers—famed QB Tom Brady, Morning Joe co-host Joe Scarborough, some Trump family members, his former attorney and known “fixer” Michael Cohen, Bill O’Reilly, Jeanine Pirro—Williams’ appearance was a head-scratcher. Was this a mistake? Or does the Serena Williams actually have a relationship with the former president that we simply didn’t know about? And if so, is it (or was it) friendship bracelet–level serious? Let’s investigate.

So, there’s this list. What is it again? 

As we all know, former President Donald Trump is currently on trial in New York facing 34 counts of falsifying business records related to his alleged payout to adult film star Stormy Daniels, which was allegedly meant to keep her quiet about their alleged affair. Trump has pleaded not guilty and has denied the affair and, therefore, the underlying accusation that this payout was “hush money” meant to preserve Trump’s chances of winning the 2016 election.

Late last week, a former White House gatekeeper for the Trump administration, Madeleine Westerhout, testified. In her testimony, emails exchanged between her and Rhona Graff, Trump’s former personal assistant and longtime Trump Organization employee (who had already testified), were shown. In these emails, Westerhout can be found asking Graff for a list “of people that [Trump] frequently spoke to.” That Excel spreadsheet includes … one Serena Williams.

I see. So, were they actually … friends? Do we have any proof or knowledge of Williams and Trump being chummy in the past?

Williams and Trump have certainly crossed paths a few times that the public knows about, though the instances are not necessarily proof of closeness, and certainly don’t answer the question “ ‘Frequently contacted’ … why?” In 2015, as the Washington Post put it at the time, Trump “invited his pal” Williams to volley a bit in a celebratory tennis bout in honor of the new tennis center opening at the Trump National Golf Club in Sterling, Virginia. In the course of the center’s opening ceremony, Trump complimented Williams by praising her recent Vogue cover, dubbing her the “greatest” female tennis player.

At the time, after asking her whom she’d vote for in 2016, Tennis Now reported that Williams claimed she would bow out, because she doesn’t “get involved in politics” or vote, due to being a devout Jehovah’s Witness, a religious belief that supports political neutrality. As far as how they know each other, Williams said at the time that she had met Trump “several times” because they both live in Palm Beach, Florida, and “everyone in Palm Beach kind of know[s] each other.” … Sure!

Wait—did we all know that Serena Williams was a devout Jehovah’s Witness? Am I alone in being absolutely gobsmacked by this?!

Sorry to say, but we all knew.

Fine, so it was just me. Have Trump and Williams been connected in any other instances?

Our first evidence lies in Trump’s failed 2000 attempt to stage a next generation Battle of the Sexes tennis match—originally fought between Billie Jean King and Bobby Riggs in 1973—with either Serena or Venus Williams volleying against John McEnroe. Apparently, this idea was inspired by McEnroe’s unsavory comments in a 2000 New Yorker interview, during which McEnroe asserted that any male senior tour member or male college player could beat the young Williams sisters. This comment notably ruffled many a feather, but apparently it only invigorated an opportunistic Trump, who allegedly offered McEnroe $1 million to play one of the sisters at his Atlantic City casino, Trump Taj Mahal. According to Newsweek, Richard Williams, the sisters’ father, expressed disinterest, while Venus made a joke, suggesting that it’s not “fair to put a 20-year-old against a fortysomething.” (If all this sounds familiar, it’s because McEnroe said nearly the same exact thing again in a 2017 NPR interview.)

Returning to 2015, we have a report that Williams danced with Trump at his New Year’s party. Trump tweeted support to Williams after her 2016 victory at Wimbledon, and again in 2020 after Williams defeated Jessica Pegula in the ASB Classic, at which point Trump said Williams was “a great player and an even greater person.” (An educated guess?)

There have been a few other times where the Williams and Trump names have been connected in the news, albeit superficially. For example, there were headlines juxtaposing Williams’ support of Colin Kaepernick’s 2018 Nike campaign with Trump’s lambasting of it. Also in 2018, a reporter infamously asked Williams about some sexist comments Trump allegedly made in 2004. The reporter, Bill Simons from Inside Tennis, said to Williams that Trump told Simons in a 2004 interview that he thought the reason Williams might have lost Wimbledon to Maria Sharapova that year was because Williams was intimidated by the Russian player’s attractive looks. Understandably, more people took issue with Simons asking Williams about the statement than Trump (allegedly) making it.

OK, that’s certainly quite the timeline. But I still can’t tell: Are they friends? What could they have been talking about, during all those “frequent contacts”?

I think they are friends just as much as the one person you see at those business conferences once every quarter, or the person you see at your regular HOA meetings. They’re neighbors, for one! And as sure as I am that not everyone in Palm Beach knows one another, I’m also sure that being of a certain level of wealth and fame will inevitably put you in rooms full of people who are also at, or beyond, that level.

Nevertheless, what does it mean, legally speaking, to be found on this list? Should I be worried for Serena?

My intelligent colleagues who are tirelessly covering this trial assure me that Williams won’t come into legal harm’s way because of her presence on this list. The introduction of the document served to prove that specific people playing a part in the trial were on it, and the other appearances (like Tom Brady and Williams) are just fun fodder for the gossip mill that pays me. I think I speak for a lot of people when I say: phew.