Bill Ackman, the billionaire financier, has succeeded at pretty much everything he’s done, professionally and otherwise. He built his hedge-fund, Pershing Square Capital Management, into a winner. He backed President Trump’s third campaign — and second term. And he’s a prolific poster on social media, regularly plopping long treatises on X, which helped him become internet-famous.
Tennis, however, is different.
That was the lesson seemingly taught on Wednesday afternoon when Mr. Ackman, 59, and his doubles partner, the retired professional Jack Sock, lost in straight sets to a pair of journeymen in front a sweaty and well-heeled crowd at the International Tennis Hall of Fame in Newport, R.I., a famed summer retreat for Gilded Age industrialists.
The loss came in the Hall of Fame Open, an official tournament of the lower-level ATP Challenger tour, which effectively made Mr. Ackman a tennis pro, if only for a day. It fulfilled a lifelong ambition — and, more than likely, he said, ended his career.
“I feel like maybe it’s one and done,” Mr. Ackman said, in the wake of his and Mr. Sock’s 6-1, 7-5 defeat, noting he wanted to support younger players getting their tournament slots — and shots. “But I figured one, in my life, that seemed fair.”
Some spectators, however, had different interpretations.
“Another mega-billionaire living out his own private dream,” said Lydia Chambers, a tennis fan from New Vernon, N.J., who was watching the match. “I hope he’s making a huge donation.”
Indeed, Mr. Ackman’s day in the sun seemingly fit into the proud — and occasionally tragic — tradition of very rich men doing athletic things and embarking on adventures, sometimes with questionable qualifications. Ballooning and sailing stunts are popular, as is spaceflight. And, of course, politics.
But tennis, as noted before, is different: a sport whose psychology has been endlessly analyzed, a test of talent and tactics known to bring even the greats to the point of despair.
“The depressing thing about tennis is no matter how good I get,” the comedian Mitch Hedberg once quipped, “I’ll never be as good as a wall.”
Some commentators were particularly aggrieved by Mr. Ackman’s sudden ascent to the level of professional play.
“Whether it’s Wimbledon or the lowest-rung tournament in tennis’ minor leagues, there aren’t any shortcuts to getting in,” wrote Dan Wolken, a columnist for USA Today, adding, “Unless, of course, you’re billionaire hedge fund guy Bill Ackman.”
Tennis, too, has been known to attract what the British author Martin Amis once euphemistically called “personalities” — egotistic sorts who think their prowess at hitting a ball is a license for bad manners. And on Wednesday, some courtside observers quietly grumbled about Mr. Ackman’s hubris in thinking he could compete with professionals.
For his part, Mr. Ackman said he has long been a tennis fan and player, though he rowed as an undergraduate at Harvard, long before he turned the attentions of his platform on X — 1.8 million followers and counting — to attacking the university.
Just last week Mr. Ackman announced, on X, that he was playing “the best tennis of my life” and had accepted an invitation to play with Mr. Sock at the Hall of Fame, adding of the venue’s 3,100-seat capacity that “there are no bad seats.”
There were, however, some bad shots, particularly at the beginning of Mr. Ackman’s afternoon, which was played in muggy conditions on a manicured grass court. His first return of serve landed about 20 feet from the net — his side of the net. His second return was slightly better, at least, landing squarely in the netting. And his first time serving — already down, 2-1, in the first set — didn’t go much better: there was a double fault, an unforced error and a volley into the net. 3-1.
But Mr. Ackman wasn’t playing alone. Mr. Sock, 32, is something of a ringer. A two-time doubles champion at Wimbledon — another grass-court tourney currently underway — Mr. Sock also boasts a U.S. Open doubles title and an Olympic gold medal. Once a top-10 singles player, he announced his retirement in 2023, and now — like so many retirees — plays pickleball.
Some in the crowd openly wondered what it had taken to get Mr. Ackman on Court 1, regardless of who he was playing with. Tournament officials, though, confirmed that Mr. Ackman played as part — and partner — of a “wild card” entry granted to Mr. Sock, who was eligible for it as he won the 2021 doubles title at the Hall of Fame. (Mr. Ackman is a major donor to the institution as well.)
Their opponents were the Australian duo of Omar Jasika and Bernard Tomic, both very competent players — Mr. Tomic was once a top-20 singles player — though neither is a household name.
Mr. Ackman’s early stumbles led to some sharp criticism from avid tennis fans like Margie Russell, a Hyannis Port, Mass., resident who was watching from the comfort of a private party being held at a porch overlooking Court 1.
“Don’t turn around and look at your partner because you’re going to get slammed with a shot,” Ms. Russell said. “Rule One is never turn your back on the net.”
That said, Mr. Ackman had also drawn a clutch of supporters, including one who had brought a handmade sign, featuring a pair of floating Ackman headshots and a slogan: “59 and In His Prime!”
One fan, Angus McIntosh, said he found Mr. Ackman’s efforts “impressive,” and applauded him for following his passions. “It takes guts,” he said.
In his X post announcing his professional debut, Mr. Ackman had suggested his performance might be a landmark, and that he might be “the oldest person in tennis history at 59 to win ATP points,” which are used to rank male players and are awarded to winning players or doubles teams.
A spokesman for the ATP Tour said, however, that Mr. Ackman would have been the third oldest to be ranked: still younger than Lars Elvstrom, a little-known Danish player who was nearly 60 when he retired with points in the bank. Another even older player, Gardnar Mulloy, was 64 when he earned his final ATP points, but those had come in a loss during an era — the 1970s — in which players could earn points for just playing.
Mr. Ackman avoided such complicated distinctions, mind you, by losing. But he and Mr. Sock did make it interesting in the second set, with Mr. Ackman’s high point likely coming in the sixth game, when he smashed a pair of solid winners, including an overhead slam, and evened the set at 3-3.
A small chorus of “Way to go, Bill!” was heard, and for a moment, it seemed like Mr. Ackman might just continue his lifelong success story with a come-from-behind win.
But tennis is different: Even as he seemed to find his stroke, Mr. Ackman’s double faults and unforced errors soon returned.
After just 1 hour 7 minutes, the Ackman era was seemingly over, though many who watched said the billionaire had done reasonably well.
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Mr. Ackman himself seemed pleased, if slightly spent, as he left the court with security personnel and a spokesman. In a quick interview, Mr. Ackman, sweat still dripping down his brow, admitted to being nervous to show his skills, something that seemed surprising even to himself.
“I could give a speech to 2,000 people, no problem,” he said. “But to get in front of 150 people and play tennis is a little different.”
Jesse McKinley is a Times reporter covering politics, pop culture, lifestyle and the confluence of all three.
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