You’re not a coward,” says David “Awesome” Lawrence, the former Wall Street executive turned fight trainer, poet, and rapper. Awesome says I’m not a coward, even though I know he’s wrong. He says I only think I’m a coward—because I only think I don’t want to climb in the ring with another fighter. What I’m really afraid of, he says, is killing the other guy. I think he’s wrong; I can’t count the number of times I've turned the other cheek. I've turned so many cheeks I feel like a figure from a Picasso painting.

Yet here I am, back at Gleason’s Gym in Dumbo. Gleason’s is an anachronism in the New Improved Dumbo, where Lawrence—also something of an anachronism—has been a trainer since the late ’90s. I'm there to confront myself and develop some swagger along the way. By becoming a boxer—or at least training to be one—I am enjoying the fantasy that maybe I could get into the ring with someone and box them. Someday. I will enact payback, I believe, that will purge me finally of some horrors from my past: when Kerry Fordyce beat me up in the high school gym, and the time the redneck scout troop from Wakulla County beat up my brother while I stood by.

Lawrence trained me briefly a decade ago along with a fellow reporter from The Chemical Market Reporter. We had decided to box in one of the White Collar tournaments invented by Lawrence that Gleason's hosted on a regular basis. This was before White Collar got collared by the boxing commissioner for not being “sanctioned,”whatever the hell that means.

“Where did you disappear to?” he said once he’d figured out—sort of—who I was. Actually that was not the first thing Awesome said when he strolled up to the entrance desk. “Who are you again?” was the first, then apologetically, “Memory, too many fights. Brain damage.” He says CAT scans showed he’d taken too many punches, had been knocked out too many times as an amateur and pro. “I didn’t want my fights to go to the score cards,” he said. Who does?

“First amateur fight, I was knocked out by a transit cop from the police team who hit me with an overhand right. Woke up on the canvas,” he tells me. “I was unconscious on my feet so I fell awkwardly; separated my shoulder and tore ligaments, but I woke up enjoying myself because I said, ‘I’m still alive.’ It wasn’t a slow beating, the way it can be in other fights: chin broken, nose broken. It was fast.”

The walls of Awesome’s office are festooned with stories about him from the ’90s in all the New York papers, in USA Today, health magazines, hip-hop magazines, fight books, you name it.

With a Ph.D. in literature, Lawrence did a stint teaching at Hunter College, then left in the ’80s to start an insurance business. “I was basically an intermediary for other brokers on big accounts. I had several offices, fifty people working for me. I had all the money I could ask for.” His toy of choice was motorcycles, but his chauffeur, a young kid, died on one, so his wife made him quit the bikes. He took up boxing.

After his first fight in a Wall Street charity match—“All the brokerage firms sent their errand boys. I sent me. I got stuck against a kid who had 25 fights, he knocked me down three times.”—Awesome became an amateur fighter until the early ’90s, when the state boxing commissioner discovered his age. “I was fighting illegally because there was a 35 age limit and I was 38.” That’s when he started the white-collar league, basically for anyone who wants to lace up gloves and fight. “I fought twenty of those and won all of them. Then the commissioner closed it, so I went pro.”

Pro at age 43. Bernard Hopkins is the oldest fighter to hold the Middleweight World Championship, and George Foreman was the oldest to win the heavyweight belt, but Lawrence has the distinction of having been the oldest person to turn pro. His first bout was in Denver, where he climbed into the ring with a Mexican fighter “Who knocked me out cold in the first round. But I was off to the pros now, and I thought, ‘So I didn’t do too well but maybe I could do better next time.’”

His next fight was in Vegas, through Don King Productions, who got him sanctioned with a phony birth certificate, “So they put me on the card. And I knocked the guy out in the second round, came back, and the commissioner who blocked me now let me fight because I had that knock out. So I was one and one. Then I went to Atlantic City and knocked out a guy in Trump Plaza, then another guy.” He knocked out the next four, then went up to Boston for a fight and the guy was too strong, too big. “He knocked me down three times in the first round and they stopped it.”

It was 1993: Awesome was signed up to fight in Madrid when his business crashed and he was sent up river for two years on a tax felony. “I got in there, and these black guys came up to me in jail, and I didn’t know what was going to happen. But they said, ‘Aren’t you the Renegade Jew?’ and suddenly I was protected.”

Awesome did three rap albums: one in the early ’90s and a couple when he got out of jail upstate. “Then I came out, and didn’t know what to do so I continued with my rap, and was at the gym, hoping to get another fight at 46 years old. I was just crazy enough to think I could do it, get a fight; and also my rap was coming along, and I was getting noticed a little, on TV, on radio, getting charted on Billboard.” He came out with his business gone and not much money. What cash he had he spent trying to kick-start his music career. “I got some radio play, but you need to spend big marketing dollars to get produced.”

One of the things he did when he got out of stir was modeling gigs. Awesome was on those subway posters with MTA employees kneeling down to help a homeless guy beside a station staircase. He was the homeless man.

Lawrence started training fighters and wannabes in the late 1990s when White Collar was still happening at Gleason’s. And he traded hip-hop for poetry. “Because I know I’ll never have to worry about making it as a poet,” he says. When he isn’t writing verses about the three-minute buzzer, the racket of loose-jointed lockers in the men’s room, or shouting trainers (“Come on, man, move to the right, man! To the right! Stay off the ropes”), he’s training people—most like me, plus a couple of Golden Gloves contenders. No serious fighters. “I can’t make money training fighters unless the fighters make money. I’d rather get paid,” he says.

In our hour together on Fridays, I feel lucky if I don’t have a heart attack by the end. The workout is anaerobic, which means you can’t breathe. It’s not like riding a stationary bike. Between rounds Lawrence tells us the next routine, slipping on a pair of mitts. “Duck under left, right and five hooks to the body.” And you do that again and again, hoping after two minutes that the three minutes are up and you didn’t hear the bell.

Then you go to the heavy bag, maybe: “Okay, I call this the Hobbit: hunch down, hard body shots, left-right, put your whole body into it.” Afterward, he pulls me aside while another trainee, Hamilton, works the heavy bag. “You want to spar? Maybe four weeks?” “Sure, why not.” “With Hamilton?” “He’s like twenty years younger than me; he’ll kill me. Look at him.” Hamilton is destroying the heavy bag. “Okay, okay,” he says. “We’ll go with someone older.” I’m thinking of ways to get out of it already. The bell rings, round over.

“All right. We’re finished; I’m tired. I’m going home,” he says. We head for the locker; Awesome grabs the mitts, speed bags, gloves and heads for his office. “Hey,” I call after him, “you coming to the fight?” There’s to be an amateur series on Saturday, fourteen bouts, three rounds each. “No,” he calls back. “My wife won’t let me watch any more. She’s afraid I’ll get back in the ring. See you next week. Hey, don’t disappear again for ten years,” he adds. “I may not be here.”

He heads back to his office and I head to the locker room. I hear a trainer calling to his fighter sparring in the middle ring, “Come on, man, show him where you from! Show him where you from!”