Bill Simons
A friend of mine couldn’t believe it. “You’re writing an article on Trump and tennis,” he sighed. “Good luck with that!”
Exactly. After we wrote our piece on Kamala Harris and tennis, I’m giving it a go.
I’m not a wealthy man. But decades ago my wife’s grandmother, Frances, became friends with the wealthiest woman in America. She and the cereal heiress, Marjorie Post, were both married to diplomats posted in Moscow. They shared elegant evenings at embassy galas before the bombs of World War II came down. Decades later, their spirits again rose when Post would invite Frances down to her Palm Beach estate, Mar-a-Lago.
For years, I’ve heard tales about grand dinners and lovely dances at the Palm Beach palace, with its classic Spanish architecture, high ceilings and stylish floors that defined the lavish place before it became a mecca for prime ministers and not-so-prime scoundrels, on-line influencers, deep-pocket contributors and a bathroom packed with secrets.
I’ve never been invited to Mar-a-Lago. I’ve never been to a Trump rally. I’m not on Truth Social. I’ve never had to testify at one of his trials or been grilled at a congressional hearing.
But I know a thing or two about the guy.
I’ve been to Trump Tower, where I went down his golden escalator and then up to his modest, quite cluttered office, with its collection of football helmets and boxing championship belts, stacks of papers and magazines and a million-dollar view of Central Park.
At the US Open, I hung out at Trump’s splashy, luxury suite, which the Guardian said was the greatest “attention-seeking and ego-stroking haven in sports.”
I walked with him along his gorgeous LA golf course that kisses the Pacific. I interviewed him (“Please, no questions about his hair”), had lunch with him – such fine clam chowder – and then put him on the cover of Inside Tennis.
I soon came to realize that, long before crowd sizes were a thing, there was just one reality in his Apprentice days that seemed to matter to Donald: ratings. He couldn’t stop talking about them.
The reason I know the world’s most famous man is because I knew his longtime gatekeeper and personal assistant, Rhona Graff. In 1980, when I started Inside Tennis, Rhona was in charge of Converse’s nationwide tennis tourney, and she bought some ads. She’d volunteered at the US Open for years, and, after she showed me the ropes at Flushing Meadows, we became friends. She was a bright, beautiful, savvy New Yorker. But for some reason, she bounced around from one ho-hum job to another, until one day she told me she’d landed a job as Trump’s third-in-command assistant.
My friends all predicted she’d be out of there in three weeks. But Rhona loved the glitz of the US Open, and I figured she’d love the glitz of Trump.
She lasted almost 40 years. We’d talk as she was about to jump onto Donald’s plane to fly off to Disney World. She moved into the Trump Tower, became a fixture on the Apprentice, and eventually had to testify for Congress in a New York courtroom and speak of a rogue publisher, a problematic doorman and a lady named Stormy.
Some 3,395 days ago, as Trump first announced he was running for president, no one imagined how he’d change the world. And, even though tennis is hardly a big deal for this golf-crazy ex-president who loves boxing and wrestling and once owned the USFL New Jersey Generals pro football team, his footprints have all been all over tennis.
For a month in 1989, he dated the stunning Argentinian superstar, Gabriela Sabatini, when he was said to be on a break from his second wife, Marla Maples.
There was his ill-fated misadventure of becoming the agent of a 15-year-old girl who he found appealing because she was a lot better than the casual players at Mar-a-Lago and she could sing, dance and model.
Monique Viele hoped to earn $2 million by the time she was 19. It was said she would become No. 1 and be the first player to both sing the national anthem and lift the winner’s trophy at the same tournament. Contracts were signed, the table was set, the hype machine ramped up – but when she first faced a bit of real competition in Tokyo she was a bust. Trump never represented another tennis player.
But virtually nothing stops Trump.
While some dismissed him as just another real estate developer who didn’t pay his bills and wanted to outdo his father, many knew he was the Big Apple’s greatest PR genius. What a gift.
So for $200,000 he rented the US Open’s best luxury suite, right by CBS’s broadcast booth. While Trump’s loyal bodyguard Vinnie looked on, the suite became an epicenter for wannabes of all stripes.
“If sportswriters charted the wind with Trump’s hair, it’s because his presence was the surest indicator of a big story,” noted writer Andrew Lawrence. Smooth-talking stock brokers, aspiring actresses, cool hipsters and media-savvy politicians all came by to be seen, along with Donald’s ex-wife, his current wife and his future wife.
Fans took note: “Hey, that’s Kevin Bacon.” “Isn’t that the Patriots’ owner, Robert Kraft?” “Look, [President] Clinton is in Trump’s box.” When bound-for-glory models appeared, impolite New Yawk fans asked, “Who’s the broad?”
One model, Amy Dorris, told the Guardian that in 1997 Trump sexually assaulted her by the bathroom of his suite. She alleged, “He came on very strong right away. It seemed typical of a certain guy – people who just feel like they’re entitled to do what they want…even though I was there with my boyfriend.” Through his lawyers, Trump adamantly denied the claim.
Meanwhile, his assistant Rhona spoke of Trump’s ascent: “Seventeen years ago I worked for a real-estate magnate who was also a celebrity. Now I work for a celebrity who also does real estate.”
Yes, one year at the US Open I got into hot water when I reported that amidst all the hullabaloo in Trump’s suite, his youngest daughter, poor little Tiffany Trump, was being all but ignored. Still, Donald-watching at the Open was a guilty pleasure for many.
To Andrew Lawrence, “Trump looked like a poor man’s vision of a rich tennis fan during his appearances – braying into his cell phone…signing dollar bills for rubberneckers, backhandedly shushing a young Barron and otherwise playing the role of Titus at the Colosseum.”
“The Donald,” as he was then known, would go and sit in one player box after another. And if his player was losing, he’d cross the stadium to sit in the winner’s box.
Here’s a newsflash: he relished all the attention. Sports Illustrated’s S.L. Price said it “was impossible to resist his playboy aura…It looked like he owned the US Open.” But then in 2015, after he’d begun his race for the presidency, he was booed. He’s never returned.
Soon Trump got his revenge. In the 2016 Republican primary, three of the 16 foes he demolished had tennis connections. Jeb Bush, the first to go, was on the University of Texas team until Kevin Curren, who reached the 1985 Wimbledon final, came to Austin and bumped him off the team.
Donald then went after Marco Rubio. Writer R. Bruce Anderson compared the Floridian to the appealing but winless Anna Kournikova: “Marco presents pretty well, but even a cursory look at his record as a senator turns up almost nothing.” Trump dismissed Rubio, claiming, “The one thing I learned from sports – I was a very good athlete – is that when you’re a choker you’re always a choker.” The last Republican who Trump booted out of the primary was Rick Santorum, the brother of the longtime head of the Professional Tennis Registry, Dan Santorum.
Trump’s tennis connections seem as frequent as his rallies.
Donald’s niece Mary claimed that years ago Trump’s young buddy, Joe Shapiro, who later married the tennis icon Pam Shriver, took Donald’s tests for him, which allowed him to get into the University of Pennsylvania’s prestigious Wharton School of Business. But Shriver insisted that her ex-husband “always did the right thing, and that’s why this hurts…It feels unfair.”
In 2004, Trump generously gave an interview to me. After he got out of his limousine at the Trump National Golf Course on a magical expanse of coastline south of LA, he began with quite the charm offensive. He gestured to me and told his entourage, “This guy has got a great tennis magazine. I read it all the time.”
Soon we were walking his course, and then, in his expansive clubhouse, we began our lunch with some soup. Donald asserted, “This is the best clam chowder in the world!” Thirteen years later, I chuckled when I heard that after a dinner with President Xi Jinping, Trump said that he and the Chinese leader were having the “most beautiful piece of chocolate cake that you’ve ever seen.”
Donald talked about The Apprentice’s lofty ratings obsessively – he couldn’t stop. He added that he always hires the best people, he had the best box at Ashe Stadium, he built the best buildings and the best clubs and golf courses, and, “Then they just sort of take care of themselves.”
I referred to a quote by Abraham Lincoln in Trump’s book, “The Art of the Deal:” “If you want to test a man’s character, give him power.” Donald interrupted, asking, “What does that mean?”
I replied, “It means that anyone can deal with problems, but when you give someone power, that’s when…”
Trump cut in, saying, “Well, I’ve seen many people change a lot with power. I’ve seen people get better, but usually people get worse. I’ve seen it politically. All of a sudden they become total monsters. And they usually crash and burn.”
He then spoke glowingly of 17-year-old Maria Sharapova: “Her gait is magnificent, and those shoulders. You don’t often say ‘Gee, she has beautiful shoulders,’ but her shoulders are…She’s beautiful. But I would say that maybe Sabatini was the most beautiful.”
He reflected on Maria’s 2004 shock win over Serena in the Wimbledon final, claiming that Williams “is used to looking like the star. Now all of a sudden she was facing this girl who’s a supermodel beauty…She looked across the court and said, ‘I’m playing against a supermodel.’ I think it had an impact.”
He added, “Aura is the whole thing. Perception is an amazing word…But it doesn’t always work. The perception was that Serena couldn’t be beaten, but she got her ass kicked. So, you never know.”
Eleven years later, Serena danced with Trump, her Palm Beach neighbor, at his New Year’s Eve party.
At his recent New York trial for fraud, an Excel sheet Rhona had worked on revealed that Serena was on Trump’s frequent call list. Then, in a New York Times interview, Serena was asked about it. She bristled. “I mean, is this what this interview is about?…I talk to a lot of presidents. 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.”
Players, of course, have various views on Donald. At Wimbledon, John Isner said, “I’d love to have Trump come watch me. That would be awesome.” Caroline Wozniacki said Trump would always be welcome in her Players Box. Pat Rafter and Andy Murray both celebrated after their Open wins at Trump properties, but Murray later mocked him online. The former WTA player Nicole Gibbs said Trump should listen more and consider others. “Sometimes he presents himself as a very self-absorbed or self-obsessed character.”
Almost a decade ago, Billie Jean King said she liked meeting Donald at the US Open. But she added that he was a self-absorbed narcissist and that his race against Hillary Clinton in 2016 was “definitely a battle of the sexes.”
Billie Jean said, “Trump is just like Bobby Riggs…He’s so completely self-centered and it’s never his fault…‘Ah, I’m such a victim, I just won’t do the next debate.’…He just goes on and on.”
And Trump’s connections with tennis go on and on, too.
Melania Trump opened a controversial tennis pavilion at the White House. When Patrick Hannity, the son of the Trump-friendly commentator Sean Hannity, was on Wake Forest’s winning NCAA championship tennis team, Donald invited the Demon Deacons to the White House. And, lest we forget, for Halloween, Andre Agassi and Steffi Graf dressed up as the Trumps.
And while speaking at a New Jersey rally this year, Trump’s speech was undermined by a verbal hobgoblin.
He was trying to say that President Jimmy Carter was thought to be a great leader in comparison with Joe Biden. But he confused Jimmy Carter with Jimmy Connors: “Jimmy Connors is also happy. Jimmy is a very happy man. Both of them because, you know what, they want him out. Jimmy Connors had a bad reputation. Right now, he is considered a totally brilliant president by comparison [to Biden].”
Never one to miss a beat, Connors quickly superimposed a picture of himself on an old Carter campaign button and said, ” Who knew?! #Connors 2024.”
