At twenty-six, at the embarrassing end of a series of attempts at channelling Kerouac, I was beyond broke, back in my home town, living in my aunt and uncle’s basement. Having courted and won a girl I had courted but never come close to winning in high school, I was now losing her via my pathetically dwindling prospects. One night she said, “I’m not saying I’m great or anything, but still I think I deserve better than this.”

That fall, my uncle called in a favor and soon I was on a roofing crew, one of three grunts riding from job to job in the freezing open back of a truck. My fellow-grunts, Leon and John, were the only black guys on the crew, and hence I was known as the Great White Hope. Once everyone had seen me work, I became the Great White Dope. Our job was to move the hot tar from a vat on the ground to the place on the roof where the real roofing was done. Leon had a thick Mississippi accent and no top teeth. He stayed on the ground, pulleying the smoking buckets up to us, muttering obscenities at passing grannies and schoolgirls. John was forty-two, gentle-voiced, and dignified, with a salt-and-pepper beard and his own roofing tools, which he brought to work every day, even though he was never allowed to do anything but lug tar. John had roofed all his adult life, and claimed to have virtuosoed his way into this job by appearing on the job site one day and outshingling the best white shingler.

“I guess I don’t remember that,” said Vic, our supervisor.

“I don’t think you were there that day maybe,” said John. “It was Lawrence hired me.”

Lawrence was dead now, a famous Fezziwiggian presence, mourned by all.

“You are so full of shit,” said Vic. “If you were so fast then, why are you so shitty now?”

“You roof like my mother,” said Gary, the owner’s brother.

“Maybe your mother roofs good,” John mumbled.

“She don’t,” said Gary. “But still she’s faster than you.”

All that fall, John grieved over the fact that he was not allowed to do the real and dignified work of a master roofer.

“It ain’t right,” he’d say to me. “I can do it. They need to give me a chance. I’m an older man. Got responsibilities. Can’t just keep carrying tar my whole life.”

In late November, talk turned to the yearly Christmas party. Drinks and food were on Warner, the owner. People got shitfaced. Also, there was gambling.

“Then we’re gonna see,” Vic said one day. “We’re gonna see if John here is a better gambler than he is a roofer.”

“You gotta hope,” said Gary.

“As a roofer, John, face it, you suck,” Vic said. “Nice guy, shit roofer.”

“Too fucking slow, John,” Gary said. “We keep giving you chances and you keep screwing it up.”

“But maybe why he’s a shit roofer is he’s a gambling man,” said Vic.

“What y’all are gonna find out is I’m a roofer and a gambler both,” said John.

“Excuse me saying it,” Vic said when John had gone down to help Leon load the cauldron. “But that is a prime example of nigger-think. He thinks he’s a roofer because he says he is. Thinks he can gamble because he says he can.”

“Has fourteen kids and lets the welfare pay,” said Gary.

One payday John asked could I give him a ride home. I gave him a ride, but, it turned out, not to his home. We drove deep into South Shore, past houses we’d roofed, then into an area too poor to roof, down a block of slumping two-flats.

“My friend’s place,” John said. “I’m gonna get you and your lady some Sherman Juice so you can have a little party.”

What was Sherman Juice? We’d started drinking at the shop and I was now too drunk to ask. In the kitchen, under duelling photos of M.L.K. and J.F.K., sat an ancient black woman in a rocking chair. A mad kid dashed around, humming at me: You devil, you white. John’s friend did not have any Sherman Juice but did have a Polaroid of his girlfriend going down on him. In the photo, taken from his P.O.V., we could see, in addition to his penis, his feet, in black socks. She was looking at the camera, smiling, sort of.

“Wow, is she pretty,” I said politely.

The friend and I sat there together, admiring her. Then John and I went somewhere else. Where we went was John’s wife’s apartment. They lived apart. Living apart, they got more money, and with more money they could buy a house sooner. In the apartment was a TV and fourteen kids around it. John named them, rapid-fire, with only a few stumbles.

“You really have fourteen kids,” I said.

“Yes, I do,” he said. “Every one mine. Right, baby?”

“I should hope so,” said his wife.

No chairs, no couch, newspapers on the windows. John and his wife cuddled on a blanket.

“When we get our real house, you come over,” John’s wife said. “Bring your lady.”

“Bring your lady, and we’ll all of us have dinner,” John said.

“I hope that day come soon,” said John’s wife.

“I hope it come damn soon,” John said. “I don’t like all this living separate from my babies.”

The kids giggled that he’d said “damn.” He went around kissing them all as I paced and lectured myself in the hallway, trying to sober up for the long drive home.

As long as it didn’t snow, we could roof. Every morning, I woke at four, checked for snow. If there was no snow, I called in. If someone skillless and slow might be useful that day, Warner told me to come in. I rose, put on all five of my shirts (I had no coat), and drove down in my Nova, de-icing the windshield as I went, via reaching out the window and hacking with a putty knife I kept for that purpose.

From the roofs, the city looked medieval, beautiful. I wrote poems in my head, poems that fizzled out under the weight of their own bloat: O Chicago, giver and taker of life, city of bald men in pool halls, also men of hair, men who have hair, hairy men, etc., etc. On the roofs, we found weird things: a dead rat, a bike tire, somebody’s dragon-headed pool floatie, all frozen stiff.

Mid-December then, and still no snow. Strange Chicago crèches appeared in front yards: Baby Jesus, freed from the manger, leaned against a Santa sleigh half his height. He was crouching, as if about to jump; he wore just a diaper. Single strings of colored lights lay across bushes, as if someone had hatefully thrown them there. We patched the roof of a Jamaican immigrant whose apartment had nothing in it but hundreds of rags, spread across the floor and hanging from interior clotheslines. Nobody asked why. As we left, she offered us three Diet Rite colas.

Then it was the Christmas party. The way we knew it was festive was the garage had been cleared of dog shit. It had also been cleared of the dog, a constantly barking mutt who even bit Warner. He bit Warner, he bit the shovel head Warner thrust at him, sometimes we came in and found him resolutely gnawing the leg of the worktable with a fine sustained rage. Tonight, festively, the dog was locked in the cab of a truck. Now and then, he would hurl himself against the windshield, and somebody, festively, would fling at the windshield a plastic fork or a hamburger bun. The other components of the festivity were a plate of cold cuts on the table where normally the gutters were pre-bent, a garbage can full of iced beer, and a cardboard box holding some dice.

We ate, we drank, the checks were distributed, we waddled drunkenly across South Chicago Avenue to the Currency Exchange to cash the checks, after which the gambling began. I didn’t know a thing about gambling and didn’t want to. I rolled my four fresh hundreds and put them in the front pocket of my tar-stiff jeans, occasionally patting the pocket to make sure they were still real.

Finally, in terms of money, I got it: money forestalled disgrace. I thought of my aunt, who worked three jobs and whom I had not yet paid a dime for food, and of my girlfriend, who now paid whenever we went out, which was never, because my five shirts were too stained with tar.

“You ain’t gambling, Leon?” said Vic.

Leon said something nobody understood, and disappeared out the door.

“I suspect Leon is pussy-bound,” said Gary.

“Smart man,” said Vic.

John did gambler things with his shirtsleeves, spat on his hands, hopped around on one foot, blew on the dice. Then he laid his four hundreds out near the craps box and gave them a lecture: They were to go forth and multiply. They were to find others of their kind and come scampering back.

Vic had gone to the bank that morning. He showed us his roll. It held maybe three thousand dollars. His wife didn’t dare say shit about it. Who earned it, him or her? “I do,” he answered himself.

The gambling began. One by one, the guys lost what they felt they could lose and drifted back to stand against the worktable and diddle with the soldering irons. Soon only John was left. Why was John left? Vic kept taunting. A whole autumn of such taunts now did their work. All belittled men dream of huge redemption. Here was John, dreaming. In response to John’s dreaming, Vic and Gary began to speak with mock-professorial diction.

“Look at this, kindly look at this,” Vic shouted. “John is not, after all, any more a gambler than he is a ergo roofer. That is, he is a equally sucky gambler as he is a suckass roofer.”

“Are you saying,” said Gary, “that his gambling, in terms of how much does it suck, sucks exactly as much as does suck his roofing?”

“Perzackly, yup, that is just what I am saying, doctor,” Vic burped.

John burned. They were going to see. They were going to see that the long years of wrongs done him had created a tremendous backlog of owed good luck, which was going to surge forward now, holy and personal.

And see they did. Soon John was down to his last hundred, and then he broke it, and then he was down to his last twenty. Then Vic cackled, and John threw his sole remaining five at Vic’s chest. Vic caught it, kissed it, added it to his tremendous wad.

A light went on in my head and has stayed on ever since: It was all about capital. Vic could lose and lose and never really lose. Once John dipped below four hundred, he was dead. He was dead now.

Which was when Warner came in and passed out the bonus checks.

Warner was the owner, the big man. Tonight he was wearing a tie. Afternoons he drove from site to site in his Lincoln, cranking out estimates, listening to opera, because, he said, though it was fag music, it floated his boat.