What might a billionaire lose at? Turns out, tennis. Bill Ackman — founder of Pershing Square Capital Management, personal fortune pushing $9.5 billion — tried to tick “pro tennis player” off his bucket list. He did it on one of the sport’s official stages, the Hall of Fame Open in Newport, Rhode Island. Partnered with Jack Sock, a three-time grand slam doubles champion, Ackman faced Australians Omar Jasika and Bernard Tomic. They lost. Badly. 6-1, 7-5.
For Ackman, it was a dream fulfilled. “I feel like maybe it’s one and done,” he told The New York Times. “But I figured one, in my life, that seemed fair.”
But fair is exactly what many argue it wasn’t.
Dreams versus deserved spots
To some, this was a rich man playing out his fantasy at the expense of pros clawing for real ranking points and prize money. Former US Open winner Andy Roddick didn’t mince words. “This was the biggest joke I’ve ever watched in professional tennis,” he said on his Served podcast. “You don’t give a wild card to someone who 50 players at my club are better than.”
The backlash was instant. Martina Navratilova chimed in, “Apparently you can buy yourself a wild card. Oh to have the confidence…” Tennis journalist Jon Wertheim put it bluntly: “This would’ve been fine for a pro-am. For a sanctioned event with points and prize$? It was, at best, wildly inappropriate and lacking in integrity.”
Ackman insists he didn’t pay for the chance. The Hall of Fame Open confirmed no cash changed hands, in line with ATP rules. But the optics don’t lie: a billionaire hobbyist standing where young grinders should be.
Wild card, wild debate
Wild cards exist for good reason. Young talent on the rise. Stars returning from injury. Local favourites who can pack a stadium. This wasn’t that. Sock, who retired in 2023 and now plays pickleball, asked for a wild card as a past champion. He chose Ackman as his partner — though they’d never met before.
Ackman made no secret of his excitement. “I am playing the best tennis of my life,” he declared on X, where he’s known for lengthy posts and occasional conspiracy detours. He told followers he’d been hitting with greats like Roger Federer in casual sessions. Practice is one thing. The pro tour is another.
The stage fright of a billionaire
If Ackman’s wealth could buy him a slot, it couldn’t buy him calm nerves. He admitted as much afterwards. “I can speak in front of an audience of a thousand people or in a TV studio on a broad range of topics without any preparation and without a twinge of fear, but yesterday I had my first real experience with stage fright,” he wrote on X. “My wrist, arm and body literally froze… I had difficulty breathing.”
Despite his nerves, the match drew a mix of polite applause, polite mockery and polite confusion. Lydia Chambers, a fan watching in Newport, summed up the mood: “Another mega-billionaire living out his own private dream. I hope he’s making a huge donation.”
Why tennis is different
Money talks in many corners of life. Not on a tennis court. This sport is a test of one thing above all: whether you can hit the ball better than the person across the net. No speech, no hedge fund, no billion-dollar position can save you. You win or you don’t.
Dan Wolken of USA Today nailed the point: “Whether it’s Wimbledon or the lowest-rung tournament in tennis’ minor leagues, there aren’t any shortcuts to getting in… Unless, of course, you’re billionaire hedge fund guy Bill Ackman.”
Sure, tennis has always had its share of big egos. Martin Amis once called its characters “personalities” with a gift for bad manners. But even the brashest must earn their place through wins, not wire transfers.
This whole stunt grates because it jars with tennis’s reputation as a meritocracy. Jannik Sinner, Carlos Alcaraz, Coco Gauff — they didn’t buy their way in. They earned every point. Even Jessica Pegula, daughter of billionaires, couldn’t shortcut the grind. Win matches, rise up. Lose, drop out. Simple. Brutal. Fair.
What rankles many is that this was not a pro-am charity hit. This was an ATP Challenger event — a stepping stone for hungry players who live tournament to tournament. For them, a wildcard can be life-changing. Ackman’s cameo made it feel like a joke.
Unsurprisingly, there won’t be one. He knows it. “I feel like maybe it’s one and done,” he shrugged, sweat dripping, security at his side. Some cheered him on. Others, like Roddick, are still shaking their heads.
In the end, Bill Ackman didn’t break tennis. But for a brief moment, he bent it — and reminded everyone why, at its best, this sport is meant for those who fight for every point, not those who buy the right to swing for them.
(with inputs from NYT)
For Ackman, it was a dream fulfilled. “I feel like maybe it’s one and done,” he told The New York Times. “But I figured one, in my life, that seemed fair.”
But fair is exactly what many argue it wasn’t.
A tennis update. I met @NickKyrgios on @X and he proposed we play an ATP tournament together. Unfortunately, Nick got injured so our doubles hopes have been delayed, but fortunately fate intervened. @JackSock managed to get a wildcard into the @TennisHalloFame Hall of Fame Open… https://t.co/YR0IDQsi17
— Bill Ackman (@BillAckman) July 2, 2025
Dreams versus deserved spots
To some, this was a rich man playing out his fantasy at the expense of pros clawing for real ranking points and prize money. Former US Open winner Andy Roddick didn’t mince words. “This was the biggest joke I’ve ever watched in professional tennis,” he said on his Served podcast. “You don’t give a wild card to someone who 50 players at my club are better than.”
The backlash was instant. Martina Navratilova chimed in, “Apparently you can buy yourself a wild card. Oh to have the confidence…” Tennis journalist Jon Wertheim put it bluntly: “This would’ve been fine for a pro-am. For a sanctioned event with points and prize$? It was, at best, wildly inappropriate and lacking in integrity.”
Ackman insists he didn’t pay for the chance. The Hall of Fame Open confirmed no cash changed hands, in line with ATP rules. But the optics don’t lie: a billionaire hobbyist standing where young grinders should be.
Wild card, wild debate
Wild cards exist for good reason. Young talent on the rise. Stars returning from injury. Local favourites who can pack a stadium. This wasn’t that. Sock, who retired in 2023 and now plays pickleball, asked for a wild card as a past champion. He chose Ackman as his partner — though they’d never met before.
Ackman made no secret of his excitement. “I am playing the best tennis of my life,” he declared on X, where he’s known for lengthy posts and occasional conspiracy detours. He told followers he’d been hitting with greats like Roger Federer in casual sessions. Practice is one thing. The pro tour is another.
The stage fright of a billionaire
If Ackman’s wealth could buy him a slot, it couldn’t buy him calm nerves. He admitted as much afterwards. “I can speak in front of an audience of a thousand people or in a TV studio on a broad range of topics without any preparation and without a twinge of fear, but yesterday I had my first real experience with stage fright,” he wrote on X. “My wrist, arm and body literally froze… I had difficulty breathing.”
Despite his nerves, the match drew a mix of polite applause, polite mockery and polite confusion. Lydia Chambers, a fan watching in Newport, summed up the mood: “Another mega-billionaire living out his own private dream. I hope he’s making a huge donation.”
Why tennis is different
Money talks in many corners of life. Not on a tennis court. This sport is a test of one thing above all: whether you can hit the ball better than the person across the net. No speech, no hedge fund, no billion-dollar position can save you. You win or you don’t.
Dan Wolken of USA Today nailed the point: “Whether it’s Wimbledon or the lowest-rung tournament in tennis’ minor leagues, there aren’t any shortcuts to getting in… Unless, of course, you’re billionaire hedge fund guy Bill Ackman.”
Sure, tennis has always had its share of big egos. Martin Amis once called its characters “personalities” with a gift for bad manners. But even the brashest must earn their place through wins, not wire transfers.
This whole stunt grates because it jars with tennis’s reputation as a meritocracy. Jannik Sinner, Carlos Alcaraz, Coco Gauff — they didn’t buy their way in. They earned every point. Even Jessica Pegula, daughter of billionaires, couldn’t shortcut the grind. Win matches, rise up. Lose, drop out. Simple. Brutal. Fair.
What rankles many is that this was not a pro-am charity hit. This was an ATP Challenger event — a stepping stone for hungry players who live tournament to tournament. For them, a wildcard can be life-changing. Ackman’s cameo made it feel like a joke.
Unsurprisingly, there won’t be one. He knows it. “I feel like maybe it’s one and done,” he shrugged, sweat dripping, security at his side. Some cheered him on. Others, like Roddick, are still shaking their heads.
In the end, Bill Ackman didn’t break tennis. But for a brief moment, he bent it — and reminded everyone why, at its best, this sport is meant for those who fight for every point, not those who buy the right to swing for them.
(with inputs from NYT)
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