If you can’t beat the market, try the match point. That seems to be the new motto of a billionaire who’s gone from hedge funds to holding a tennis racquet. Well, back in 2020, he made $2.6 billion betting on a pandemic crash. Just a few years earlier, he lost nearly $4 billion. He’s taken on everything from fast-food giants to Ivy League presidents. Now, at 59, this polarizing Wall Street power player is attempting one of his most unexpected moves yet, entering the world of professional tennis. While most eyes are on Wimbledon’s second week, this billionaire is quietly preparing to make his ATP debut on the grass courts of Newport, Rhode Island.

And if he wins even a single match, he could become the oldest person in tennis history to earn ATP ranking points. The man behind this bold new chapter is Bill Ackman, the outspoken CEO of Pershing Square Capital Management and one of the most controversial figures in modern finance.  But instead of shorting stocks or calling out CEOs, he’ll now be sharing a court with Olympic gold medalist Jack Sock at the Hall of Fame Open, an official ATP Challenger event. Confused? Ackman is now turning his competitive energy toward tennis. He’s set to play in the men’s doubles event alongside Jack Sock, a former pro who retired in 2023. How is it even possible?

Well, the wildcard entry came through Sock’s request and was approved by the ATP, blending a fan-favorite former pro with a wildly ambitious amateur. For those thinking this is a casual publicity stunt, think again. Ackman trains seriously, hitting four to five times a week and playing daily in the summer. He’s played with and against elite players, including Roger Federer, Andre Agassi, and Stefanos Tsitsipas. In fact, he recently reached the semifinals of the Finance Cup, a grass-court event held on the same Newport courts. He also helped fund rising American star Frances Tiafoe in his junior years.

With matches kicking off Tuesday, Ackman and Sock are set to train briefly in Bridgehampton before arriving in Newport. Ackman has agreed to play the deuce side to match Sock’s strengths and says he’s “peaking next week.” While the $2,030 prize money will go entirely to Sock, Ackman isn’t in it for the cash; he’s chasing legacy, adrenaline, and perhaps a bit of redemption in a very different kind of arena. As he puts it, “It’s a once-in-a-lifetime experience—unless we win.” But could he really pull off a win at 59? Well, don’t count him out; this is the same guy who once beat Andre Agassi in doubles. Surprised? So were most people.

The $4 Billion blunder that drove Bill Ackman back to his first love, tennis

Bill Ackman’s love for tennis started long before he made headlines on Wall Street. Growing up in Chappaqua, New York, he picked up a racquet as a young boy and went on to play competitively at Horace Greeley High School in the early 1980s. That early passion never faded. Even as he built his reputation as a hard-hitting hedge fund manager, tennis remained a constant. He once considered building a tennis court on the rooftop of his Manhattan office, and he’s been known to train regularly, even practicing up to 90 minutes a day in the summer.

Over the years, Ackman’s hobby evolved into a high-level pursuit, putting him across the net from some of the greatest players in tennis history. In the early 2010s, he warmed up Andre Agassi before a charity match against Pete Sampras at Madison Square Garden, later claiming he actually beat Agassi in a casual doubles game. He also hit with Roger Federer, though he admitted nerves got the best of him. Perhaps his most memorable moment came in a charity match around 2016, when he lobbed a ball directly at John McEnroe without warning, drawing a signature outburst from the tennis legend. Of course, not all of Bill Ackman’s bets have paid off, and one in particular cost him nearly $4 billion.

In 2015, riding high on past wins, he took a massive swing at Valeant Pharmaceuticals, believing its bold business model of snapping up smaller drug companies and hiking prices was the future of pharma. At least he seemed a genius for a short time. However, there were the cracks: dubious connections to a mail-order drugstore named Philidor, unholy soaring drug prices that attracted criticism among the populace, and investigations by both the SEC and Congress. Withdrawing is not what Ackman does best; he bet it all in, and to turn around, he even sat on the board of the company. It was not successful.

The stock tumbled from $260 to less than $11 and in 2017, Ackman exited, leaving nothing but one of the costliest bets in hedge fund history. He later called it “one very big mistake,” a humbling chapter that reshaped his strategy and perhaps reminded him why the tennis court, not the trading floor, was always his favorite place to play.