Opening a kilo of coke takes time. The outside layer of this particular package bears a colorful pattern of palm trees that makes it look like a birthday present, a thick paperback maybe. Other layers nest beneath the trees: layers of plastic, of carbon paper, of tracing and butcher paper, one stamped producto de calidad and numbered. Below the first layers, the entire brick is slathered in diesel-engine degreaser to keep it moist and mask the smell from detection dogs. Jesse attacks the package with a pocketknife and his fingers, showing neither haste nor undue caution. After all, he has done this many times before. Yet there is something about the kilo that makes it different from the rest; it is, Jesse says, the first kilo of the last shipment of cocaine that he will sell here in Pittsburgh, bringing to a close a successful career that began when he was eleven.

The kilo shucked, Jesse begins his real work: making the cut. Straight from the brick, the cocaine has a gummy texture that would prevent its being chopped into fine lines on tabletops, mirrors, and toilet lids. Jesse paid $187,000 for the shipment of seven kilos, or about $757 per ounce. Since Jesse sells ounces for a thousand apiece, he would make a profit of roughly $250 an ounce or $4,000 per kilo—a decent return. Yet, by using a proprietary recipe to double the weight of his product, Jesse will actually make more than three times as much on every kilo. Through an act of chemical prestidigitation, the seven will become fourteen and $4,000 will become $20,000. Even after Jesse treats it, the chunky coke retains a pearly sheen. “That ‘fish-scale’ shine is what you look for,” Jesse says, “but it’s not 100 percent reliable.” It matters little to Jesse that his buyers believe he is supplying them straight from the source. “They all beat the hell out of it anyway,” he says.

It’s hot in the attic in late July; Jesse is wearing a pair of Bermuda shorts, a carpenter’s mask, and a black bandana pulled low over his brow. (He calls it his “Hamburglar” disguise.) Just over six feet tall, Jesse has broad shoulders, though a flange of gut droops over his waistband. He sweats as he shakes the whirring grinder, fingers stained with ink from the degreaser-soaked carbon paper. Agitated molecules fly around the room. The smell of acetone and coke stain the air. “I used to get a room at a tellie [hotel] for this,” he says. “But that was actually pretty stupid. All weekend long the only thing you could hear coming out of there was the sound of the grinder: wheeeee-wheeee.”

It goes against Jesse’s instincts to have me watch what even his business partners haven’t seen. I’ve known him for less than two weeks. I’m a writer. My being here is the best measure of how serious he is about leaving.

Amid the grow lights, bongs, plastic baggies, and squeeze bottles, the attic holds hundreds of dancehall, funk, afro-beat, and hip-hop LPs, as well as turntables from Jesse’s second job as a nightclub DJ. While Jesse mixes and grinds, he has me put on records from the collection. He has only one request.

“Don’t play any roots reggae,” he says. “Because we are definitely not doing the Lord’s work up here.”

I first met Jesse at the Original Fish Market restaurant at the Westin Convention Center in desolate downtown Pittsburgh. Under a nebula of Japanese lanterns, businessmen with ties flipped over their shoulders lectured women in evening gowns. The Fish Market was a place to impress a date, to bring important clients, to celebrate an anniversary. The menu featured entrees like “Sous Vide of Label Rouge Scottish Salmon Filet” and three hundred wines by the glass. Jesse slouched through the room, his shambling walk the result of baggy jeans belted low and unlaced sneakers, tongues flopping out. Skinny dreadlocks stretched to his waist and his electric blue t-shirt bore a big print of the rapper Just-Ice. The waiters greeted Jesse by name and quickly ushered us to a table.

“I eat here like three days a week,” Jesse said. “And they know how I tip.” In his custom sneakers and designer baggies, Jesse could have been a music producer or an urban-wear entrepreneur.

At the Fish Market, Jesse may have been hitting a vodka-cranberry while sipping a fifty-dollar glass of wine, but he still knew the wine was corked and sent it back. After a flurry of text messages, Jesse announced that another guest would be appearing. “This isn’t one of my A girls,” he said. “More like the B squad.”

The B-Girl, aka Andrea, appeared and nestled into Jesse’s arm. With her soft voice and guileless brown eyes, Andrea radiated sweetness. She’d just finished a bartending shift and drained a double vodka tonic in one satisfied swallow.

“It’s like the commercial,” she said apologetically. “Vodka gives me wings.”

The waitress ran back and forth, sweat dappling her temples. A happy Jesse might pay her rent for the month. As a friend of Jesse’s put it, “He’s like Brad Pitt in that motherfucker.”

From our table, we watched Andrea walk off to the bathroom.

“They all got asses like that nowadays,” Jesse said. “I don’t know what they’re feeding them in high school. Maybe creatine and oatmeal.”

“Does she know about you?” the Mumbler said. A lanky man with ginger hair and a scruffy beard, the Mumbler favored shades of purple, lavender, and orange and looked like a cross between a candy raver and a Viking. He had brought me to Pittsburgh and introduced me to Jesse. We called him “The Boston Mumbler,” because he talked in a low tone that, combined with his New England accent, often made him incomprehensible.

“All she knows about me,” Jesse said, “is that I smoke copious amounts of trees and my paper just don’t stop.”

The gangster was talking like a gangster should. In fact, the whole night was a gangster paradise: pretty girl, fancy restaurant, fawning waiters, Jesse thumbing cash from a big roll. But I knew that Jesse had reasons to worry. The previous fall, his oldest friend had been arrested with nearly a million dollars in cash, much of it Jesse’s. Soon afterward, Jesse’s girlfriend broke up with him on the night of his twenty-ninth birthday (although Leslie still lived in his house). With his friend’s trial coming up, Jesse worried that he would be indicted too. His anxiety showed in small things. At dinner, he took two bites of his filet mignon then left the rest in a congealing pool of sauce.

On my second day in Pittsburgh, Jesse gave me a civic tour. The Mumbler was driving. The Mumbler steered his mauve rental Cadillac down side streets and back alleys while Jesse talked. Jesse knew the drug corners, he knew the boundaries of school districts, and he knew the cost of real estate. Pittsburgh had fallen a long way from being the industrial powerhouse of history, when schoolteachers brought students to classroom windows to see coal black skies. “That means your daddy is working,” the teachers would say.

Beautiful is not a word associated with that Pittsburgh. But I loved the views from the green hills, I loved the old mansions and ornate public buildings, and I loved the abandoned warehouses and dead factories. Pittsburgh felt like a frontier: rough but with more freedom than you could find in other places.

For the same reasons I loved Pittsburgh, Jesse hated it.

“There’s nothing to do here, man,” he said. Where I saw decaying grandeur and cheap rent, Jesse saw a wasteland where crime was the only way to make money. “This town is a desert with a keg of beer,” Jesse said. “There’s nothing here for me and I was born here. This city is full of people living below their capabilities because there’s only so far you can go. All people think about is where they’re going to eat, what they’re going to drink, and who they’re going to fuck.”

We drove through eastern Pittsburgh into Braddock where Jesse grew up. In the 1950s, Braddock had a population of over twenty thousand. In 2000, it had fewer than three thousand. The national media liked to highlight Braddock as an icon of metropolitan dysfunction. The movie The Road was also shot there. The Road is set in the United States after a nuclear holocaust. The Hollywood people didn’t have to change very much about the town.

“Look at that steel mill,” Jesse said, pointing out the Cadillac window. “It’s not running. They’re actually tearing it apart for scrap. So everyone you see working is here disassembling this bitch.”

Driving the Cadillac through his old neighborhood made Jesse uneasy. Despite his gangster uniform, Jesse worked hard to lower his profile. He didn’t own a car and paid his rent in cash. Only a few people knew where he lived, he used a “burner,” and once went a full year without a phone at all. If someone got an inkling of what he did, Jesse shrugged his shoulders and said, “That was years ago. My glory days are done. I’m retired now.” Unlike most criminals, Jesse saved his money and had stashed it in safes across the city. Jesse’s caution (and luck) explained why he’d never been arrested on drug charges. Caution also explained why he wanted to quit dealing. “Look at the odds,” he said. “The jakes only have to get lucky once to ruin your life permanently. And you on the other hand, you have to get lucky every second of every single day, forever. I can’t say I like those odds.”

We couldn’t go to the housing project where Jesse grew up—it had been demolished. Instead, we drove down the empty main street.

“When I was a kid,” Jesse said, “this street right here used to be the shit. There were three fucking movie theaters on this street. You could shop for anything under the sun. Now look at it.”

He pointed to the boarded-up storefronts, to the five closed banks.

“It’s early as fuck,” Jesse said. “That’s why you don’t see the hustlers out. Don’t think they ain’t out though. They’re just in all these weird-ass little cuts. The fucking feds be down this bitch now like heavy, man. They’ll just come out here and choke you out and make you eat a laxative and sit on a bucket right in the middle of the street. I’m not even fucking with you.”

I went with the Mumbler to pick Jesse up after he put in his coke order. Jesse jumped into the car, and we slid through the empty downtown Pittsburgh night. Unlike Jesse, the supplier, or “hook,” didn’t seem at all worried about drawing attention to himself.

“He’s got a guy who tastes all his drinks for him,” Jesse said. “And another guy who cooks for him. I mean, he went right into the restaurant kitchen and made the food. How is that not going to get people talking? Meanwhile, the dude’s got eight cell phones all ringing at the same time. Hanging out with him is not a fun experience. I’m sure the feds are checking him out. There’s probably CIA guys hiding in the bushes. It’s crazy, man.”

Jesse’s supplier came from Miami to Pittsburgh for business, always taking a suite at a luxury hotel. The man’s staff—his taster, his cook, his bodyguards—was made up of old friends. “Even the brokest dude drives a Bentley,” Jesse said. Having friends act as a support staff made perfect sense. Jesse’s supplier was running a multi-million dollar operation and needed to be able to speak freely (to an extent) and relax (to an extent).

“Did you tell him you were leaving?” The Mumbler said.

“Hell no. I’m just going to stop showing up.”

“Won’t he miss your money?”

“Let me tell you,” Jesse said, “this is just a sideline for him. He won’t miss it. He’s asked me numerous times to take fifty [kilos]. And when I’m like, no, I don’t have the paper for that, he says, ‘Don’t worry, you can owe me.’ But I say, ‘No thanks.’ I’m not about to start owing this guy money.”

Jesse never made more than one order per month and never for more than he could pay with cash on hand—usually five to fifteen kilos.

The supplier had told Jesse that the shipment would arrive the following Wednesday, at which point he would call Jesse. The money and the drugs were never in the same place at the same time.

“How do you know the hook?” The Mumbler said.

“I’ve known dude a long-ass time. His old man used to buy herb from my dad. He never liked me but he knows me.”

Jesse’s paternal grandfather was a West Indian numbers runner who committed suicide. His mother was the illegitimate daughter of a respected jazz musician. Jesse’s father was a hustler. Some of Jesse’s earliest memories are of bales of marijuana on his kitchen table. Jesse’s father made up for his infrequent visits home by knocking his son around. As Jesse put it, “He was into some crazy tough-love shit. Once he punched me in the chest so hard that I flew across the room and knocked over the refrigerator. I remember thinking, ‘Well, nobody my own age is going to hit me like that, so I got nothing to be afraid of out there.’” Along with beatings, Jesse’s father provided entrepreneurial advice. “He told me: ‘You’re not selling the product. You’re selling yourself. Remember that.’ I think I was like nine at the time.” Otherwise, Jesse’s father kept out of his son’s life. “I hated that man until I was twenty-nine years old, but he raised me just like he was raised,” Jesse said. “Now I realize that he was giving me the tools I needed to survive.”

Because of federal anti-racketeering laws, Jesse didn’t spend much time with his father. “I don’t need to have no RICO charge come down on us,” Jesse said. Jesse’s father had never involved his son in his illegal activities. When Jesse started dealing, it was entirely on his own initiative. Jesse discovered his calling in the third grade when he started selling candy at school. “I used to flip candy and shit,” he said. “Those rich kids didn’t know how cheap it was in the ghetto.” At eleven he turned to a more profitable Braddock staple: crack cocaine.

“I had thirty-five dollars and I wanted to make more,” Jesse said. “I’m dead-ass serious with you. So I bought what they call a double up and I just kept doubling it. Crack was everywhere. I was on the street, know what I mean? If you’re outside all day, even at six years old, you know the motherfuckers who got whatever. It’s not hard to tell the pimp. It’s not hard to tell the dude selling crack.”

Calculated risk taking, calm under pressure, and an ability to identify markets and suppliers: Jesse was a model businessman. At fifteen, he found a source for low-cost, high-quality marijuana: a hippie supplier in Vermont. Too young to drive, Jesse would ride Greyhound dressed as a soldier, going so far as to shave his head and bring the marijuana home in an army duffel bag. When the hippies began to treat him poorly, Jesse robbed them, carting away a trunkful of marijuana and cash. Jesse didn’t mind ruining the connection, as he’d already identified a better source: an Indian reservation on the Canadian border.

Yet Jesse had problems with his new supplier. “You got green berets up that motherfucker,” Jesse said. “You got border patrol and the res cops and you got the fucking UN police because of the terrorism shit.” There were also state police roadblocks just outside the reservation. Jesse found the Indians to be unreliable business partners. “They don’t like anybody,” he said. “Anybody. They’re still so pissed off that motherfuckers took their land. And on top of that, there’s no organization. Them sneaky crook fucks will fuck their own brother over.” Jesse managed the Indians by bringing them a drug that wasn’t available locally: cocaine. “You talk that ‘soft’ shit to ‘em,” he said. “Oh my God. They’ll fucking shoot their mom in the fucking forehead to get it.”

The reservation made Jesse as a dealer. The marijuana was cheap, high quality and abundant. “We were doing like three hundred [pounds] a weekend,” Jesse says. Soon the issue became finding someone to smuggle the drugs. Everyone was getting rich, and with money came caution. “So you can’t talk to the broke dude,” Jesse said. “Like, we know you need some money, so you’ll do it just because you got to.” They solved this problem by bribing the owner of a salvage yard near the reservation. Jesse would pack wrecked cars with marijuana. The cars would then be loaded on flatbeds and driven to Pittsburgh. As Jesse put it, “Who’s gonna fuck with the local dude who they call every time they tow a car?”

As Jesse got older, he dumped his money back into the business. Having a cash reserve meant he could wait for the best connection and buy bulk at the lowest price. With the Indians, Jesse found himself doubling and tripling his money until the money became a headache and he had to cram it into the succession of safes. As crazy as the reservation might have been, the money was good and nothing ever happened bad enough to make Jesse stop. “We did that shit for eleven years,” Jesse said, “and we never lost a load.”

Jesse preferred selling the high-grade marijuana to cocaine because the risk/benefit ratio was lower. “Clip me with a three hundred pack of weed,” Jesse said, “What’s that gonna do? Motherfucker, I’ll only do six months. But if I get hit with three grizzles [grams] of coke, I’m fucked. Especially if you have it in separate plastic bags.” But in that bad winter after his friend’s arrest, Jesse turned to cocaine. It started when Leslie’s mother complained about the quality of the cocaine she was selling to supplement the income from her hair salon. “I told her, ‘I can probably help you out,’ and I talked to some people.” Leslie’s mother also gave him the key ingredient to the recipe for his cut. Jesse’s entrée into the market came during a citywide cocaine drought and customers lined up. As Jesse said, “Shit ain’t worth dick if everybody got it. Sometimes I’ll pretend like I don’t got shit for two weeks. Just so I can charge a fucking hundred bucks more. Per clip. You do that three, four hundred times, that’s another fucking forty grand.”

“I’m just a piece of trash from the gutter,” Jesse told me with pride. “I was born to be what I am. I come from a family of hustlers. Know what I mean? Most people at family reunions. They talk about their kids and who got married and shit. At my family reunions, everyone talks about how much paper they made on their last hustle, and how bad they fucked somebody up.”

One night, as Jesse waited for the cocaine, he bought seven pounds of marijuana and brought it to Scooter’s house. Scooter was a big man with an even bigger beer belly and upholstered with tattoos. One of the biggest tattoos stretched across his gut and read, lunchbox. (Scooter had lost a bet.) I assumed he was in his forties, but he said he was only thirty-one.

“That’s not what you do Scoot,” Jesse said. “You got to peel the shit . . . ”

“I peeled it,” Scooter said. “And then I broke it up.”

“No, roll it around in your hand and shit so it breaks up.”

We were sitting in Scooter’s filthy bedroom where Jesse had opened the box full of midi-brick marijuana. “Midi” referred to the middling quality of the marijuana and “brick” to the fact that it had been compressed before shipping, probably in a trash compactor. Jesse was giving Scooter a lesson on separating the sticky marijuana buds.

“I peeled a piece off,” Scooter insisted, “and I broke that up.”

One of Jesse’s uncles had called a few hours earlier looking to get rid of the midi. Jesse knew someone who would buy midi and the deal was made. Now Jesse was separating the buds in an attempt to get more money out of his buyer. Separating the buds helped to restore them from their compressed state. While compression made the marijuana easier to transport, it diminished potency. The buyer would still know that it had been compressed, but if the buds looked good, he might decide that he could do further work and sell them for a higher price. (There were techniques for restoring bud volume involving humidifiers and steamers.) Breaking the buds only created “shake”—loose shreds and flakes.

Jesse’s cocaine order was supposed to have arrived a week earlier. The midi was an opportunity to make a few thousand dollars while he waited. Jesse wouldn’t even smoke the midi—“That crap gives me a headache,” he said. But money was money.

Jesse slowly parted two buds.

“See how it’s like pieces?” he said. “Peeeel it. Peel each piece. That’s the only way it’s going to pop back. It’s not going to make any difference if you just break the chunks into smaller chunks. See what I mean? They’re actual fucking buds that they just laid in the bitch.”

Scooter shook his head. When it came to drugs, he remained an earnest amateur. Scoot was part owner of the Darkside Lounge, a bar that provided most of his income. He referred to the money he made from coke as “play money.” Scooter used the play money to take women out, buy gifts and, when he was inebriated, emphasize whatever point he happened to be making by tossing handfuls of the money at you. The Mumbler had told me that Scooter’s father had been in the Mafia and died young.

“I didn’t break it like that,” Scooter said.

“I just watched you do it,” Jesse said.

Scooter had first gotten to know Jesse as a fellow DJ. Only after Scooter bought the bar and Jesse made it his hangout did the two start working together.

“This job sucks,” Scooter said.

“You wanted to be number two,” Jesse reminded him.