A little more than a year ago, one of the world’s wealthiest financiers spent 67 minutes on a grass tennis court with three professional tennis players, playing a match in the sport’s minor leagues at one of its most hallowed venues.
It didn’t go well.
The financier was Bill Ackman, the 60-year-old chief executive of Pershing Square Capital Management. He has an estimated net worth of about $10.4 billion, depending on the day, the shifts of the financial markets and the success of the bets he has placed within them. He was at the International Tennis Hall of Fame to try to fulfill the pipe dream of a wealthy amateur athlete — to see if he could become the oldest player to collect ATP Tour points, by testing his wares against the pros in an actual professional tournament.
Ackman also can sometimes seem like he is nearly everywhere in tennis these days, the man behind the curtain prompting certain things to happen in the sport. That day, he was visible and his tennis was vulnerable.
A promising junior from a family with limited means needs money for coaching and travel? There’s Ackman, who provided a teenage Frances Tiafoe with more than $100,000, which changed his life. Tiafoe will play Friday for a spot in the U.S. Open men’s singles final.
Novak Djokovic, the 24-time Grand Slam champion, wants to create a players’ union, and he needs money to launch it? There’s Ackman again.
Tennis centers in the Bronx and Washington need to rebuild or refurbish courts — or end up on the receiving end of a $10 million endowment? Ackman.
An annual team tennis event among members of the financial world that includes solid club players, former college stars and some former big and small names from the recent and distant past of professional tennis? That is Ackman’s event.
So last summer, when the International Tennis Hall of Fame in Newport, R.I., had granted a wild card at its Challenger Tour event to a doubles team that consisted of Jack Sock, a former world No. 8 in singles and a four-time Grand Slam winner in doubles, and a 59-year-old who had last played competitive tennis in high school, it was no surprise to those in the sport that Ackman was a part of it.
Ackman declined to be interviewed for this story.
Lots of wealthy people write big checks to gain access to world-class athletes and professional sports. But almost none of them would ever dare to step onto a playing field with those athletes in an official event.
After 20 years of using his money to embed himself within tennis, funding its development and regularly playing with and against former top college players and touring pros of nearly every level, Ackman’s part in the wildest tennis match in recent memory was, for some, an affront to the fundamental integrity of sports.
For Ackman, it was just an inevitability.
In 2004, Jeff Appel, a top-ranked tennis junior in the 1970s and 80s, was rising at a hedge fund and becoming known for helping bring talented tennis players into new careers on Wall Street. He has since recruited and mentored more than 150 players into finance careers.
He also paired the best players for friendly matches. 22 years ago, he emailed Ackman, who was developing a reputation as a successful activist investor, on a whim. He asked him to play.
A doubles outing ended with Ackman taking everyone to dinner at Sparks Steak House, in midtown Manhattan.
So began Ackman’s 20-year odyssey in the sport. Tennis became an obsession. He began hiring top talent to coach and hit with him; he built a tennis court on top of the midtown Manhattan office building that serves as the Pershing Square headquarters. That way, at any time he could grab one of his employees and practice.
There wasn’t much about the tennis world he wasn’t interested in.
In 2008, Ray Benton, a longtime Washington lawyer who helped create the men’s professional tennis tour, took over the Junior Tennis Champions Center. JTCC’s mission was giving less-advantaged children with tennis talent an opportunity to develop into top players, without having to move to Florida or Europe to attend an academy.
Benton eventually connected with Appel, who led him to Ackman, and brought a young Tiafoe to Ackman’s house in the Hamptons for an introduction. It changed the trajectory of Tiafoe’s career and his life. He and Ackman remain pals to this day.
In a recent interview, Tiafoe, whose father was a maintenance worker at JTCC, said he remembers first laying eyes on the houses of the ultra-wealthy, from whom Benton sought donations.
“Eye-opening,” Tiafoe said. “Like, this is where tennis can take me, to be in houses like this and play, you know, against CEOs and CMOs, big billionaire-type guys, hedge fund guys.”
Frances Tiafoe, who will play in the U.S. Open men’s semifinals, is a beneficiary of Ackman’s financial involvement in tennis. (Mike Segar / Reuters)
Robin Montgomery, a promising American who has had to manage a wrist injury in recent years but who on Wednesday made the U.S. Open women’s doubles final, also met Ackman on one of those trips and has received significant support from him. It’s common for Ackman and Appel to email her after her matches.
As he was building up his relationships, Ackman was also working on his game. There was no level of player he didn’t want to play with or against, especially given Appel’s access as a matchmaker with all the tennis talent in the industry.
Mario Ančić, a former world No. 7 who went on to a career in private equity. Amer Delić, an NCAA singles champion and top-60 player who entered wealth management and real estate investment. Richey Reneberg, a former world No. 1 in doubles and the 1992 U.S. Open men’s doubles champion, who became a highly successful hedge fund executive after his tennis career.
In 2015, Ackman and Appel created the Finance Cup, a tennis networking event for Wall Street’s highest-level players. It has become a two-way pipeline between the sport and Wall Street’s riches.
Milos Raonic, the former world No. 3 and 2016 Wimbledon finalist, as well as a recent addition to the private equity division of Goldman Sachs, played this year.
Raonic has been getting to know Appel, Ackman and Reneberg and playing tennis with them the last couple of years as he began to plan his transition to his post-tennis life. They helped him get an offer at Goldman.
During the last decade, Reneberg has become Ackman’s favorite doubles partner, Appel said. Reneberg did not dispute that assessment.
Reneberg’s status may not be a coincidence. Over more than 25 years, he has perfected the art of making weekend-warrior financiers feel very good about their tennis skills, whether he is playing with or against them. It’s a common approach for strong tennis players who coach or hit those with weaker skills.
Tennis pros have a phrase to describe this: “customer tennis.”
“You try to put the ball in a good spot,” said Reneberg, who doesn’t use the phrase but is familiar with the concept. “You’re not hitting heavy topspin and throwing them up against the fence.”
In some ways, the best possible outcome is when the customers, so to speak, become deluded into thinking they are not that far off from the pro, a not uncommon conclusion for some highly successful people. They forget the man or woman on the other side of the net is mainly interested in their enjoyment, not showing them the vast gulf between their skills and talents.
“A lot of people think just because they’re very good at one thing that it naturally transfers to the next,” Raonic said, speaking generally about high performers in every realm.
A lot of people, he said, don’t realize how hard tennis is. Top players have to execute so many specific techniques while in constant motion. Hitting from both sides. Serving. Volleying. The best players in the world do almost nothing else from the time they are small children.
During his playing career when he participated in sponsor events and in casual games in his retirement, Raonic has become accustomed to handling people with self-aggrandizing views of their tennis abilities. Unless they ask him not to, he refrains from using his cannon serve. And even if they do want to see it, he hits it down the middle so they don’t get hit in the face.
“You kind of learn this ability to just adjust to make sure everybody is having as good of a time as possible,” he said. “Whoever is on the other side that’s kind of looking forward to that opportunity, you’re trying to make it as enjoyable and fun for them as well.”
Bill Ackman playing during the first Finance Cup in 2015. (Michael Nagle / Bloomberg)
Reneberg said Ackman had mused a couple of times in recent years about trying to enter a professional doubles tournament with a wild card. His confidence in his game had grown, and with good reason. By all accounts, he is a strong player.
Last year, Ackman rented out the lush grass courts of the International Tennis Hall of Fame to hold the 2025 Finance Cup. Within days, the facility was set to host the Hall of Fame Open, a Challenger Tour event with prize money of $200,000.
Officials had an extra wild card. In what they later described as an effort to drum up excitement, they offered it to Ackman, one of the country’s biggest tennis benefactors. Ackman had donated significant sums of money to the organization, but not in several years.
Reneberg said Ackman asked him to be his partner. He told him he was thinking all wrong. Reneberg has the serve of a 60-year-old former pro.
“Playing with me, we could easily lose love and love,” Reneberg said he told Ackman. “I said, ‘John Isner’s your guy.’”
But the 6-foot-10 Isner, who retired in 2023 and is known for his big serve, was not available.
Sock was. He retired in 2023 after a solid career, especially in doubles. Sock and Ackman practiced at Ackman’s home in Bridgehampton, N.Y., over a weekend, then headed to Newport for their opening-round match July 9.
Ackman had high hopes. On social media he wrote: “I am playing the best tennis of my life and Jack is one of the greatest doubles players ever… so you never know.”
As he always does, he backed himself.
Why not? Backing himself had earned him a roughly $10 billion fortune. Plus, he’d spent all that time on the court with all those terrific players. He was friends with guys on the tour such as Tiafoe and had hit with some of them, too.
Sock and Ackman drew two journeymen, Bernard Tomic and Omar Jasika, hardly Bob and Mike Bryan.
Still, this was a real match, with money and rankings points on the line, even if it wasn’t much. First-round participants earned $1,120. The winners received another $930. But no professional wants to lose to a retiree and a 59-year-old hedge fund guy. It didn’t take long for the world to see that money can attain proximity to top tennis talent but not create a transformation into a top tennis talent.
It wasn’t pretty.
Tomic and Jasika did what pros do. They exerted enough effort to prevail, and not much more, in their 6-1, 7-5 win. It didn’t take very much.
Ackman struggled to keep the ball in play. Sock appeared to remind him before the fourth game that it was his turn to serve. Andy Roddick called it “the biggest joke I’ve ever watched.”
Ackman said he succumbed to nerves.
“Throughout the match, my wrist, arm and body literally froze with the expected negative outcomes,” he wrote on social media. “I had difficulty breathing, and it was not a fitness issue. It got a bit better as the match progressed, but I was not able to overcome it.”
He described the experience as “humbling.”
In the days after the match, a firestorm erupted after Ackman offered to create a $10 million endowment to the Hall of Fame. Under mounting public criticism of what looked like a quid pro quo, the Hall of Fame turned down the endowment offer. Officials wrote in a letter to their members that they regretted the decision to give Sock and Ackman a wild card.
Ackman donated the money to JTCC instead.
In a statement, the tournament organizers said “in no way did Bill buy his way into the Hall of Fame Open.” They gave Ackman and Sock a wild-card entry to “bring further excitement to (the 2025) tournament.” They called it a “learning experience that will help us make better decisions in the future.”
Tiafoe said he was glad the friend and patron he used to hit with had played the match. Asked why, he offered his trademark wide grin.
Appel said Ackman is a far better player than the one who was on court that day. Reneberg, who had traveled to Newport to watch the match, said he admired Ackman for taking a shot.
He wasn’t all that surprised by the outcome.