Fortress Chieftain Mike Novogratz Wrestles with Olympians, Youth…and Wall Street

“SMASH HIM,” said Ray Brinzer, the barrel-chested drill sergeant running Beat the Streets’ weekly Tuesday night workout in the old St. Anthony’s gym on Thompson Street. “If you break him, good. If you get him on the ground, sit on him. And if I see you lying there for the whole two minutes, I’m going to come and step on your head because you shouldn’t let him do that to you.” For more than an hour, 30 high school wrestlers had alternated one-on-one drills with laps around the wrestling room and other feats of exertion—wheelbarrow races, anyone?—that nearly made us sick. They wore spandex singlets and basketball shorts tucked in at the cuff in rough approximations of loin cloths and neatly proved what people around the sport kept telling us: Although the old rubber suit in the sauna routine is now illegal, the best wrestlers tend to be a little bit nuts.

The efforts appear to be paying off. In 2007, the Public Schools Athletic League fielded 19 wrestling teams. This year, there were 64, and Beat the Streets was funding another 35 programs at the middle school level—in total, the organization says it helps support nearly 3,000 wrestlers, about 85 percent of whom qualify for free school lunches. Last summer, a Curtis High School junior named Rosemary Flores won titles in two age groups at the youth wrestling national championships. And a high school junior named Cheick N’Diaye finished runner-up at the New York State wrestling tournament this year.

Unless you hail from Pennsylvania, cradle to the country’s best high school wrestlers, or Iowa or Oklahoma, the states that have long dominated the sport at the collegiate level, you may be forgiven for thinking of wrestling as a spectacle of piledrivers and body slams. But the amateur version of the sport has long been popular among future finance types.

“I wrestled as well as I could wrestle, and if I lost, that was my own fault,” KKR’s Henry Kravis once told an interviewer about what he learned from wrestling. “I had nobody to blame but myself.” Apollo Global Management co-founder Josh Harris wrestled at the University of Pennsylvania before deciding that making his 118-pound weight class didn’t allow either the time or calories for the old “college experience.” Former Goldman Sachs chief executive officer Stephen Friedman, an AAU champion who wrestled at Cornell, was known to challenge subordinates to impromptu matches. Former Merrill Lynch CEO John Thain was a college wrestler, though Mr. Novogratz pointed out that Mr. Thain, now CIT Group CEO, wrestled at the Division III level.

“Wrestlers are quick to qualify how good a guy was,” he said. Indeed: “Mike was a better wrestler than I was, but he never beat me,” said Richard Tavoso, Mr. Novogratz’s college roommate at Princeton, now the head of global arbitrage and trading at RBC Capital Markets.

Noel Thompson, a former Goldman Sachs trader who recently launched his own hedge fund, told us that wrestling was good training for traders because it taught them how to make the best of a bad position. “There’s the discovery of pain,” he said. “You learn how much you can take, and you learn how to cut your losses. You’d rather give up a takedown for two points than a throw for five.”

“A lot of the Ivy League wrestlers wind up in New York, so you have a strong set of wrestlers in the financial community,” said Martin Floreani, the proprietor of Flowrestling.org, the go-to website for American wrestling fanatics. “One of the things that Novogratz has done is to knit those guys together.”

We’d come across Mr. Floreani on Thursday evening, leaning against the mat-side risers near 47th Street and Broadway. Easily a thousand wrestling fans had gathered to watch the U.S.-Russia exhibition under a cloudy sky and millions of shifting lights, spilling out of the bleachers and onto the sidewalks, climbing atop planters and police barriers and whatever else they could find. Dan Gable, maybe America’s most famous wrestler, was there, as were John Smith, Cael Sanderson and a host of other gold medalists. An Ohioan named Logan Stieber brought the crowd to its feet with a last-second victory. Mr. Thompson donned a tuxedo and stars-and-stripes bow tie and hyped the crowd in a cheer of “USA! USA!”

“It’s surreal,” Mr. Floreani told us. “U.S. wrestling doesn’t usually get to do these kinds of things.”

Mr. Novogratz, dressed in a blue suit and purple tie, his bald head gleaming under the television lights, watched from a cross-legged perch on the edge of the mat, often zipping into the crowd to greet a friend, of which he appeared to have many. For the last four years, he’s served as something called “Team Leader” for the U.S. national team, fundraising and traveling to tournaments from Cuba to Russia and beyond. Recently, Mr. Novogratz and fellow Beat the Streets board member Dave Barry began funding a program that pays wrestlers for making the podium in international medals.

“Mike’s really injected a lot of energy into the program,” said Mark Manning, the head wrestling coach at the University of Nebraska and an assistant on the U.S. national team, adding: “He’s someone the guys can relate to. Would they like to get him on the mat and rough him up a little? Probably, but so far he hasn’t let them.”

Asked whether Mr. Novogratz had ever climbed into the ring with him, Mr. N’Diaye said he’d come close. “He tried to once, but I didn’t want to,” the teenager told us. “I’m bigger now. If he wants to step to me, I’ll step to him.”