Trump and the US Open: the rise and fall of a transactional love match | US Open tennis

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Donald Trump’s last trip to the US Open did not go as smoothly as his 2015 presidential campaign kickoff. Three months after that gold-plated escalator ride, Trump was booed upon arriving at the VIP entrance at Arthur Ashe Stadium and booed again when he was shown on the big screen during that night’s quarter-final match between Venus and Serena Williams. He hasn’t shown his face at Billie Jean National Tennis Center since.

Trump of course would be first to say he had more pressing matters to attend to over the past eight years. Currently, he’s facing four separate indictments related to his time as US president – not least 34 counts here in New York for alleged hush money payments to an adult film star. Perhaps Trump would never have sunk this low if he had stuck to his role as the US Open’s unofficial celebrity mascot instead of moving into politics. But that role also helped his late-stage career change. Nowadays, though, you’d be hard pressed to find any trace of the relationship around the US Open grounds. Trump doesn’t talk about his time here anymore. Neither does the USTA. It’s almost as if an affair that lasted nearly 40 years never happened.

Trump and the US Open were once a love match in mutual attention-seeking and ego-stroking that history struggles to appreciate now. When they began seriously courting each other in the late 1970s, the US Open had just relocated from genteel country club surrounds in Forest Hills to its current digs here on the site of the 1964 World’s Fair, with the idea of evolving into a spectacle for more than just tennis. And Trump was a small-time local real estate developer with designs on outdoing his father. But thanks to a boom in quality American tennis players, the US Open mushroomed into a cultural force that eventually sucked in Fashion Week, the MTV’s Video Music Awards and other seasonal New York rites. All the while Trump looked like a poor man’s vision of a rich tennis fan during his appearances at the US Open – braying into his cell phone well before the things were ubiquitous, signing dollar bills for rubberneckers, backhandedly shushing a young Barron and otherwise playing the role of Titus at the Colosseum.

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Trump was among the first in line for an Ashe Stadium luxury suite (valued at $200,000 for the duration of the tournament in the early 2000s), reportedly renting two at one point. (The USTA says the Trump Organization hasn’t signed another lease since giving up its box in 2017.) From that perch he became a bellwether of sorts, gossip columnists scrutinized his celebrity guests (American treasure Kevin Bacon, New England Patriots owner Robert Kraft, sitting president Bill Clinton) and fashion critics snarked at Trump’s habit of turning up in the same dark suit/bright tie ensemble like a comic book villain – The Donald, as he was known back then. If sportswriters charted the wind with Trump’s hair, it’s because his presence was the surest indicator of a big story.

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Even the glamor girls Trump chose to decorate his suite with mark time. In 1998 it was Kylie Bax, a New Zealander who had one curious fan yelling, “Who’s the broad?” In 2003 it was Lisa Cant, an 18-year-old Canadian who was being touted as the next Kate Moss. For the all-Williams final in 2001, two days before the Twin Towers fell, Trump was joined in his suite by his ex-wife, Ivana, and future wife, Melania. Nineteen years later, a former model named Amy Dorris alleged to the Guardian that Trump sexually assaulted her outside the bathroom in his private suite at the tournament in 1997 when she was 24 (via his lawyers, Trump has strongly denied having ever harassed, abused or behaved improperly toward Dorris.)

When Trump wasn’t lording over the US Open from on high, he could count on a prominent seat in the players’ box – next to then-Chris Evert beau Andy Mill for the American Sweetheart’s US Open farewell in 1989, beside Brooke Shields for Andre Agassi’s comeback tale in 1994, by himself for Caroline Wozniacki’s 2010 semi-final run (“There’s always a place for Mr Trump,” the Danish former No 1 said at the time.) Patrick Rafter celebrated his US Open titles in 1997 and 1998 with Trump at the Park Avenue Country Club. A superstitious Andy Murray was a guest at Trump International Hotel for a stint after his 2012 stay there culminated in his first career major title (Murray has since mocked Trump on X, formerly Twitter. He is one of the few high-profile players to hit out at the former president).

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Donald Trump with his phone courtside at the 1989 US Open
Donald Trump with his phone courtside at the 1989 US Open. Photograph: Ron Galella/Ron Galella Collection/Getty Images

In her 1991 title victory speech a teenage Monica Seles thanked Trump – who was rumored to have helped the world No 1 drop off the radar for a six-week stretch that saw her miss Wimbledon. “He was the one person that kind of said the whole two weeks that I could do it,” she said. The crowd had at them both. Trump never completely won them back. Boos often greeted his seemingly obligatory appearances on the Ashe big screen. Before long, the negativity became something to revel in.

It should surprise no one that, given his long history of misogyny, Trump seemed particularly keen on mansplaining his way around women’s tennis. In a 2004 Inside Tennis interview he was particularly obsessed with just-crowned Wimbledon champion Maria Sharapova – doubting her business acumen in one breath (offering up “the right management”), doting on her like a prize horse the next (“her gait is magnificent … and those shoulders”) before concluding that her looks were what ultimately pushed her past Serena Williams in the Wimbledon final. “I think [Serena] looked across the court and said, ‘I’m playing against a supermodel.’ I think it had an impact.”

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But Trump was also hugely keen on the Williams sisters. The Philadelphia Inquirer’s match report from Venus’s 1997 US Open final clash against Martina Hingis makes a point of noting how Trump celebrated her biggest winners with an approving fist pump. In 2000 he volunteered to pay in excess of $1m to sponsor a Battle of the Sexes reboot pitting either Williams sister against John McEnroe, and seemed genuinely more interested in watching a repeat of history – this time, with teenagers beating up on a middle-aged man. Trump rang in the 2015 new year dancing with Serena at Mar-a Lago. When an angry outburst at a lineswoman after a controversial foot fault call helped doom Serena in the 2009 semi-final, Trump didn’t hold back either. “[The lineswoman] had a smirk on her face and was being a wise guy,” he wrote in a post for the leadership section of the Trump University blog. “The backlash against Serena has been relentless, and she has been treated badly. She has apologized, and I think enough is enough.”

Trump was unlike any other American tennis patron, one who in the late-1980s was as wont to support the USTA’s bid to keep the Open in Queens as angle to move it back to Manhattan. At the dawn of Trump’s Apprentice fame in 2004, the USTA tapped him for a campaign to encourage participation in the sport. “If you don’t go to,” Trump said in one endorsement video, “you’re fired.” A print version of the same advert had him sitting behind a desk holding a gold racket. The women’s tour wrangled him for their own promos, too. At the time the federation celebrated him as a youth ambassador of indeterminate value. Never mind that the man himself was pushing 60.

In hindsight it’s a wonder Trump hung around the US Open for so long. When he ultimately did slink away, it was well overdue. He can draw plenty of big crowds on his own – ones that not only root him on, but help him attempt to reverse a presidential election. The US Open dominates New York’s cultural scene to the point of becoming a shrine for social climbers to practice conspicuous consumption – an all-American cultural symbol. The transactional relationship served its purpose for the tournament and for Trump. The fact that both sides appear happy to stay apart speaks to just how drastically America’s course has diverged.

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