Bill Ackman's Quixotic Quest to Play Pro Tennis — and the Firestorm That Followed

Bill Ackman, the 60-year-old hedge fund billionaire behind Pershing Square Capital Management, has spent two decades using his estimated $10.4 billion fortune to embed himself deep inside professional tennis — funding players, building courts, and cultivating relationships across the sport. Last summer, that obsession culminated in a 67-minute humiliation on the grass courts of the International Tennis Hall of Fame in Newport, Rhode Island, where Ackman and retired pro Jack Sock were handed a wild-card entry into the Hall of Fame Open, a Challenger Tour event. They lost 6-1, 7-5 to journeymen Bernard Tomic and Omar Jasika. Andy Roddick called it "the biggest joke I've ever watched."

Ackman's tennis journey began in 2004 when Jeff Appel — a former top-ranked junior who has since funneled more than 150 professional players into Wall Street careers — cold-emailed him for a match. What started as a doubles game ending at Sparks Steak House in Midtown Manhattan grew into a full-blown obsession: Ackman hired touring pros as coaches, built a rooftop tennis court atop the Pershing Square headquarters in Midtown, and began quietly reshaping American tennis philanthropy. He funneled more than $100,000 into the development of a teenage Frances Tiafoe — whose father was a maintenance worker at the Junior Tennis Champions Center — a contribution Tiafoe credits with transforming his trajectory. Tiafoe reached the U.S. Open men's semifinals this year. American doubles standout Robin Montgomery has also received significant support from Ackman.

Ackman and Appel co-founded the Finance Cup in 2015, an annual Wall Street tennis networking event that has become a genuine two-way pipeline between elite tennis and elite finance. Milos Raonic, the former world No. 3, participated this year as he transitioned into a role at Goldman Sachs's private equity division — a move facilitated partly through connections made in Ackman's tennis orbit. Former world No. 7 Mario Ančić, ex-top-60 player Amer Delić, and former world No. 1 doubles player Richey Reneberg all moved into finance through this network. Reneberg became Ackman's favorite doubles partner and is widely regarded as a master of "customer tennis" — the art of making wealthy amateurs feel competitive without exposing the actual chasm between their skills and those of professionals.

The Newport debacle had the hallmarks of a slow-motion collision that insiders saw coming. Reneberg had warned Ackman against the idea of playing with him as a partner — "we could easily lose love and love" — and suggested John Isner, whose big serve might have compensated. Isner wasn't available; Sock was. Ackman practiced at his Bridgehampton home, posted confidently on social media, and then froze on court, later describing his wrist, arm, and breathing locking up under nerves. The firestorm intensified when Ackman, days after the loss, offered the Hall of Fame a $10 million endowment — an offer the organization publicly rejected under accusations of a quid pro quo. The Hall of Fame issued a letter to members saying it regretted granting the wild card. Ackman redirected the $10 million to the Junior Tennis Champions Center instead.