(Photo: Christopher Anderson/Magnum Photos/New York Magazine)

On the wall of David Lawrence’s office at Gleason’s Gym is a copy of a Top 40 hip-hop chart from 1992. “This was a midwestern market,” says Lawrence, pointing. “I’m in the No. 2 slot. My rap name was Awesome D, a.k.a. the Renegade Jew. Second place. I beat Cypress Hill!”

A year later, in 1993, Lawrence, the chief of a Wall Street insurance firm and a semi-successful professional boxer (career record: 4-2), pleaded guilty to tax evasion, and went to a medium-security prison in the Poconos. “In the real world, I might have been a sleaze, but up there, I was the man,” Lawrence recalled. “The first thing I hear is ‘Oh, shit, it’s the Renegade Jew!’ Lawrence had obtained his Ph.D. in literature in 1976 from CUNY—his dissertation topic was the “metanovel”—and he spent most of his time behind bars writing poetry and lifting weights.

When he got out, he had barely a penny in the bank. So he went to Gleason’s, his former gym, and asked for a job. He’s been training fighters ever since. “I’m a brilliant coach,” he says, notwithstanding some new sidelines: Lately, he’s been writing anti-Obama screeds for tea-party websites. “I used to be a liberal, but I’m fed up with the dimwitted electorate,” he says, shrugging. “I should probably move to Alabama. But no. I was born in New York, and except for prison, I’ve never left. I belong here.”

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• Table of Contents: Dec 17, 2012 issue of New York | Subscribe!