On Sunday morning at 9:15, I met up with investment banker Jeffrey Appel in Manhattan’s Upper East Side.
It was my second week in a row accompanying Appel for the ritual of Sunday morning tennis on Randall’s Island to play with some of Wall Street’s biggest names.
The previous week, Appel took two young investment bank analysts — who had both played Division I tennis — on the quick, seven-minute ride out to the courts.
Shortly after we arrived at the Sportime club at Randall’s Island, Pershing Square Capital CEO Bill Ackman walked in wearing shorts and a fleece with his tennis racket in tow. He immediately began to stretch.
Appel is affectionately known as the “Mayor of New York Tennis,” bringing together the titans and some of the younger generation on Wall Street. He’s also credited for bringing Ackman back into tennis world.
Ackman played in high school at Horace Greeley in the 1980s, but he did not play in college at Harvard.
Ackman returned to the tennis world after Appel sent him a blind email in 2005 inviting him to play with his Wall Street tennis crew. Within four hours, Ackman responded and joined him the following week. He played with Appel; Kyle Kliegerman, former No. 1 at Princeton and the current head of the equity portfolio at Taconic Capital; and Jeffrey Sloves, former No. 1 at Dartmouth and current managing director of Jones Trading.
Since then, Ackman has become extremely passionate about his tennis. He frequently plays in charity tournaments, and donates significant amounts of money to various causes supported by the finance tennis community.
Appel and Ackman share a court at the Sportime center on Randall’s every Sunday. Ackman was absent last Sunday, though, because he was in Amsterdam for Pershing Square Holdings’ initial public offering.
“It’s a ritual,” Ackman told Business Insider. “What I like is it’s competitive and [Appel] puts together the best tennis in New York.”
This week, Appel, who was recently ranked No. 12 in the US for his age group and No. 1 in the east, was recovering from a calf sprain. He had to sit this match out.
There never seems to be a shortage of players wanting to join Ackman and Appel’s court, though.
There was a last-minute substitution of Rob Pohly, the CIO of Samlyn Capital Management, a multibillion-dollar long/short equity hedge fund.
Pohly was the 1991 “Rookie of the Year” in Ivy League tennis. He played No. 1 for Yale University, and he’s part of Appel’s tennis network.
A minute later, the former pro tennis player James Blake, who was ranked No. 4 in the world in 2006, walked into the club. Blake and Ackman both headed off to the courts to warm up before the other players arrived.
Ackman decided to play against Blake in the first match, rather than be his partner as Appel had suggested.
A few minutes later professional poker player Stephen Bass arrived.
Bass recently joined Larry Penn’s hedge fund Ellington Capital.
Bass, who was ranked as high as No. 354 in the world, in 2009, met Penn — Appel’s high school tennis teammate — while playing tennis. Penn and Bass have been a top doubles team in the charity circuit on Wall Street.
“Stephen and Larry make a great team because their combined mental game is far superior than their competitors’,” Appel said.
On Sunday, Bass partnered with Ackman for the first match against Pohly and Blake.
Blake and Pohly won the first two sets in a heated battle. Then they switched teams, and Ackman and Blake, the two Harvard alums, won the third set against Bass and Pohly. They were on serve in the fourth set when the two hours were up and it was time to leave the court.
Ackman was hungry play more.
“Bill Ackman is the only guy over 40 when playing the young guys that I know that gets better as the hours go on,” Appel said. “The guy can never get enough tennis. If he could, he would play five hours a day.”
On the next court over was billionaire hedge fund manager Marc Lasry, who runs Avenue Capital, and his regular Sunday game crew.
“It’s actually sad because you realise how bad you are,” Lasry said, joking, about the level of players on Ackman’s court.
He continued: “No, it’s actually great tennis. It’s phenomenal tennis. They always have different guys who come. It’s also a lot of fun to watch everybody play. You see the calibre is actually really good. Sometimes it’s James [Blake]. It’s always different guys.”
One of Ackman’s usual doubles tennis partners is former No. 1 University of Pennsylvania tennis player Jason Pinsky, who is now an analyst at Wexford Capital.
Wexford Capital is a Greenwich, Connecticut, hedge fund/private equity firm run by Charles “Chuck” Davidson. Wexford actually employs a handful of top tennis players. Brandon O’Gara, who played tennis for UPenn with Pinsky, is also a research analyst there. Former NCAA doubles champion/pro player Kaes Van’t Hof works there, too.
Pinsky and O’Gara met their CEO while playing in a regular Wednesday night open-level doubles event at the Billie Jean King National Tennis Center that was organised by Appel and Whitney Kraft. Van’t Hof first met Davidson while playing in the Richardson Invitation in summer 2011 with Appel. At the time, Van’t Hof was at Citi in the Financial Institutions Group.
According to Appel, Davidson’s first words to Van’t Hof, jokingly, were, “You’re playing with Jeff and you already have a job?” He hired him within five months to work on the private equity side of Wexford Capital.
Another member of the Wexford tennis team is Jon Pastel. Pastel, a former professional tennis player, used to practice with Davidson’s Patrick, who is currently playing professional tennis. Pastel and his wife, Marjorie, also host “The Wall Street Challenge” tennis tournament that raises funds for Ovarian Cancer research.
It’s clear that there’s a strong bond between tennis and finance.
“Many firms like to hire Ivy League athletes because if somebody was able to be a good student while also playing a sport it shows they have discipline and a competitive drive in addition to being intelligent and are able to balance multiple challenges at the same time, which gives them a higher probability of success in the competitive world of Wall Street,” Appel said.
Just last week, I observed a match taking place on Appel’s court. One of the guys was an extremely tall 22-year-old, who was a former top-ranked NCAA doubles player with a 4.0 GPA at a southern university more known for its football. Appel has taken a liking to this young man and has already brought him to play with Howard Lutnick, the CEO of Cantor Fitzgerald, and Ackman.
“He’s developing a fabulous reputation amongst the business titans,” Appel said. “I really like this kid. He’s smart and mature beyond his years. I believe he has what it takes to be very successful and I am trying to help him transition into a career on Wall Street.”
You can see why they call him “The Mayor of New York Tennis.”