Photo: Noah Shelley

(1.) The Connection

One of four phones Lenny uses for business; this one is for staying in touch with runners making deliveries. The phone numbers are prepaid, attached to no name.

(2.) The Money

About $25,000, a fraction of his savings. He nets an average of $5,000 a week and stores much of his money in a safe bolted to the floor of his apartment.

(3.) The Tools

A portable digital scale used for weighing small quantities of cocaine. For larger amounts—between 100 and 500 grams—he uses a triple-beam balance.

(4.) The Product

One ounce of cocaine, purchased for $800 in Washington Heights, bagged and ready to be sold for $2,500.

Every day he tells himself the same thing. You are doing nothing wrong. It plays through his mind on repeat, keeping his nerves in check. You have no reason to worry. Tonight, a Friday, he is walking down a cobblestone street in Soho, hands wedged in his leather jacket, his posture slump-shouldered, as if he’s curling in on himself. In his right-hand pocket, there is a plastic bag containing numerous smaller plastic bags—“tickets,” he calls them—filled with either a gram or gram and three quarters of cocaine. The smaller ones he calls “chiquitas.” They cost $60. The big ones, known simply as “big ones,” go for $100. He is heading to see a customer, a twiggy, doe-eyed woman who asked to meet outside an art gallery. He thumbs through the Baggies, able to gauge the weight with his fingertips, and secures her order in his fist, all the while humming along to the voice in his head.

You are doing nothing wrong—

This is deluded, he knows, but in his business, delusion is everything: both what you’re selling and how you sell it. His name is Lenny Starke, or at least that’s what we’ll call him here, and seven days a week he moves through the city like this: making pickups and deliveries, a sequence of handshakes and handoffs that earns him, tax-free, about $5,000 a week. This places him somewhere in the middle of the $92 billion worldwide cocaine industry, above petty street dealers, below the organized syndicates that are his main suppliers. Given Lenny’s upbringing—the socially ambitious parents, the airy Manhattan apartment, the uptown private school—dealing seems an odd career choice. But to him, it’s almost logical. His financial portfolio is impressive: $30,000 in a safe bolted to the floor of his apartment, another $25,000 in storage at a “wholesome” friend’s house, and a steady stream being invested and washed clean in the stock market. And when Lenny wants to spend a weekend on Shelter Island or comes down with a cold or just feels like staying inside and playing Grand Theft Auto—a video game in which the hero is a drug dealer—he has a rotating cast of employees who do the work for him. All this, and he is not yet 25. “I’m going to be financially set,” says Lenny. “I can skip a step. I’m able to pay for my apartment without having to work a crap job or having to ask Mommy and Daddy to send me rent checks every month—that, to me, is just as bad.”

It’s an absurdly warm night for March, still early, edging on 6:30, that hour when the tension of the workweek gets eclipsed by a restive desire to get a little lost. Lenny’s cell rings repeatedly. Per dealer protocol, the number is prepaid, attached to no name, untraceable. The phone is an old-school, beat-to-hell Nokia that he refuses to upgrade, Lenny being somewhat superstitious. “Probably it’s the warm weather, but I’m thinking tonight’s gonna be busy,” he says after taking a call, this one from a 21-year-old kid so “papered up”—Lenny’s term for those with enviable wealth—that his parents bought him an entire brownstone. “The kid is a spoiled brat, basically, who wants to pretend he’s all thugged out,” Lenny continues, seemingly unaware that the same could be said about him. “Anyway, those calls just now? That’s three more orders, and we only walked, what? Four blocks. It’s cool, but I was hoping to kick it, have a beer. I’ve been working since, like, noon, right? Went up to midtown for the day shift. That’s finance types mainly, guys in suits, some people in fashion. I meet them at their offices. Or on the street, real quick, boom-boom, you know? Or in banks, right in the lobby by the ATMs. Banks are my favorite. Nobody is thinking people are buying coke at a bank.”

Dealing has always appealed to Lenny’s two most dominant personality traits: an obsession with money and chronic impatience, characteristics that don’t exactly set him apart from his peers, kids who came of age during the hip-hop and Internet booms, two movements united by the philosophy that money is something to be made quickly, dubiously, and only in large amounts. “I was always the kid that wanted more,” is how Lenny puts it. “I never grew up with nothing, but I never had enough. If you gave me $20, I wanted $40. I like eating out, I like nice things. I can’t really function if I can’t get what I want. Ever since I was little, I would just go out and get, you know?”

Photo: Noah Shelley

But, lately, as his friends settle into careers in private-equity consulting and cosmetics PR, Lenny has found himself questioning his profession. Whenever he tries to imagine himself five or ten years down the line, his mind either shudders and comes up blank, or spits back images of clichéd cautionary tales: Lenny the Addict, Lenny in Jail, Lenny Dead. “I’m not gonna be 30 years old and feeding my babies with this,” he declares, but given that he’s often in debt up to $15,000 to a man who regularly carries a gun, getting out is more complicated than suddenly growing a conscience and tossing your phone into the East River. “You have to get out smoothly,” says Lenny. “Same way you got in.”

With this in mind, he has recently set in motion a plan for retirement, one that gains momentum with each customer he greets—

“Hey, baby, what’s up?”

Outside the gallery, the doe-eyed woman hurries across the street, her vintage riding boots clicking on the cobblestones. There must be an opening tonight, because bodies are pouring into the street, blocking traffic. Beneath the thin yellow glow of the streetlights, the figures are silhouetted: a sea of conceptualized hairstyles all referencing bands that Lenny, who listens almost exclusively to hip-hop, has never heard of.

“Yeah, baby, long time no see.”

With that, Gallery Girl presses her waxen cheek to his, kissing the air just below his earlobe. Lenny can smell her perfume—vaguely citrus, superclean. He shakes her hand, sliding the two big ones she ordered into her palm. She slips the Baggies into her purse as they walk through the crowd making small talk, two old friends who know nothing about each other. Eventually, they stop and she gives him another delicate kiss, this time reaching out her other hand, the one that’s been palming $200 the entire time.

“See ya, baby,” she says, cantering across the street and disappearing through the gallery door.

Lenny, meanwhile, goes into accounting mode.

After every delivery, he pulls out his T-Mobile Sidekick and uses its tiny keypad to record the specifics of the transaction just completed: customer nickname, quantity purchased, cash received. This information will be erased later tonight, once he gets home and downloads it into a Microsoft Excel spreadsheet tracking every deal he’s made over the past year. That file is then purged from his hard drive and stored on an unlabeled diskette: a cheap, flimsy piece of plastic that Lenny hopes will make him a small fortune. Like many markets, the drug business thrives on mergers and acquisitions, or what is known in the trade as “selling your numbers”—giving up your phone and client list for a fee. Every dealer keeps track of his profits in one way or another, though Lenny’s Excel document is likely a rare prep-school touch, one he hopes will boost his sale price. Recently, he heard about a pot-delivery service going for $50,000, but cocaine is both a pricier drug and a growth industry—use among adults has been increasing nationally since 1999—so he’s thinking he could double that number. “The rule in any business is that you don’t sell your company for what it makes in a year,” explains Lenny, “but for what it makes in two or three or four years, right? Well, in my business, you can’t do that. Someone gets arrested and—boom—it’s over. So you gotta sell it based on what you make in, like, six months.”

And that, in outline, is Lenny Starke’s retirement plan: Cash in, cash out, and use the windfall to invest in something legitimate. A business of some sort. Real estate, for instance. Maybe get an M.B.A. Every now and then Lenny even thinks, half-seriously, about law school. “Yeah, it’s ironic or whatever. People say, ‘Oh, law school, yeah-yeah … ’ But doing this has made me better suited,” he claims. “I’m a good talker, good at sitting down with people and working out deals. Half of law is the pretrial stuff you don’t see on TV, striking deals behind the curtain, which all comes down to money. Well, that’s the shit I do every day.”

To find the origin of Lenny’s hustling instinct—to understand how an upper-middle-class kid becomes a serious drug dealer—you have to go back to high school. Freshman year, he was a skinny kid, decent at sports, interested in student government. But by the time he was 15, Lenny had joined the ranks of privileged children who, searching for appealing avenues of rebellion, choose to emulate the lower classes with a cartoonish take on black culture. “Basically,” he says, “I started running around acting like a fake thug,” a pastime that revolved around “local street-dogging-type things,” like stealing North Face jackets off the backs of younger kids and skipping class to smoke blunts in back alleys. Lenny loved pot, but he also saw it as a business opportunity, partly because selling would mean free product for himself. Like his favorite rapper, Tupac Shakur, put it: I smoke blunts on a regular, fuck when it counts / I’m tryin’ to make a million dollars outta quarter ounce.

Photo: Noah Shelley

“It was almost like a hobby at first,” says Lenny. “I remember when I got my first ounce, breaking it up, how it was like a little celebration.” Moving from buyer to seller proved surprisingly easy: Just tell the guy selling you that dime bag that you’re looking to buy in larger quantities; he’d rather sell an ounce all at once than move it one gram at a time. From the beginning, Lenny displayed a knack for business. He went down to Chinatown and purchased hundreds of tiny clear-plastic cubes: blue for boys, pink for girls, his first foray into elementary branding principles. He had a stationery company print up 1,000 business cards—the word juice surrounded by palm trees, his pager number in the bottom right corner. But his greatest innovation was his distribution method: “I made somebody else sell it for me. I got the stereotypes, one of the only black kids, so nobody knew it was me.”

Then, just as the business was running smoothly, something unexpected happened: High school came to an end. As Lenny watched his friends get accepted to places like Wesleyan and Yale and Skidmore, his mailbox filled with rejection letters. He ended up at a college never once mentioned by his school’s guidance counselor, which only reinforced the notion that his talents lay elsewhere. So he expanded his services to include Ecstasy, LSD, mushrooms, Special K. In a shift so subtle he didn’t even notice it at the time, Lenny went from being a fake thug to a kid who resembled the real thing. “I’m upper middle class,” he says. “I didn’t grow up with a gun in my house, but I fell in love with that gangster shit.” He looked sharp in a fur-trimmed hoodie. His velour track pants were Sean John. He walked with a no-bullshit swagger. When a heavily tattooed kid conned him out of 100 pills of Ecstasy, Lenny sought retribution: He set up a fake deal and hired an associate to press a pistol into the guy’s ribs as they drove around Queens. “Come on, man! Please! I don’t wanna die in these streets!” he screamed as Lenny, sitting in the backseat, looked on impassively.

It was only a matter of time before one of his friends—an increasingly shady lot of outer-borough roughnecks, none of them connected to his private-school past—introduced Lenny to the cocaine trade. “One day, he pulls me aside,” Lenny recalls, “and he’s like, ‘You’ve got to check this out.’ It was a fucking manila envelope full of cocaine. Pure, powdery. No rocks, nothing. He was like, ‘I got this girl in South America, she sends it to me.’ You wouldn’t believe how many of these fucking letters come through. You can put an ounce of cocaine in there”—28 grams, about $2,500 on the street—“and by the time it gets here, it’s like a thin piece of paper.” Lenny had tried coke once before but didn’t understand the fuss people made over a substance that, to his mind, made you nervous for fifteen minutes, a fiend for two hours, then depressed for an entire day. “But I’m like, Fuck it. I did a line, and it was amazing. I traded 60 pills of Ecstasy for 20 grams. I split it up into little Baggies, then I ended up sniffing all my profits away. But I sold a little bit of it and kept in touch with the guy, and from there … ” Lenny lingers on the memory for a moment. “Well, I was serious about it.”

“I meet them at their offices. Or on the street, real quick, boom-boom. Or in banks, right in the lobby by the ATMs. Banks are my favorite. Nobody is thinkng people are buying coke at a bank.”

He was 21, barely going to class, hooked up with an anonymous South American distributor, and selling coke to friends, friends of friends, and people he didn’t recognize who swore they were friends. Somewhat unwittingly, he was building a network that tapped into an underserved demographic: white kids in their twenties who were curious about coke but didn’t have a reliable source. These were customers born in the mid-eighties—too young to have vivid recollections of the crack epidemic. By the time they were entering the prime years of postadolescent experimentation, cocaine had been socially declassified as a scourge, doing a line no more frowned upon than puffing on a joint. “Now everyone’s into coke, talking about it openly, laughing about it,” says Lenny, echoing a 2005 report from the National Drug Intelligence Center, which noted that the perceived risk associated with powder cocaine has steadily declined, especially among the young, since the early nineties. “Do you listen to hip-hop?” Lenny asks. “Suddenly, every rapper’s talking about coke.” He mentions Cam’ron, the platinum-selling Harlem artist:What you want, coke or piff? / I got it all smoke or sniff … Bird’s-eye view / The birds I knew / Flip birds / Bird gang / It was birds I flew …

“Birds,” explains Lenny, “is slang for a kilo of coke.”

The letters from South America weren’t arriving fast enough, so Lenny asked around and found another connection: a surly older guy who often had a gun tucked into the waist of his pants. “We’ve never had a conversation longer than ten seconds,” says Lenny, but he suspected that his new supplier was “mobbed up.” His product was even more pure, and reasonable at $25 a gram, about a third of the street value. (The Bush administration claims that thanks to the $4 billion war on drugs in Colombia, cocaine in the U.S. now costs $170 a gram and is 15 percent less pure than it used to be. “I don’t know who their connection is,” Lenny deadpans, “but someone’s getting ripped off.”) Lenny would buy anywhere from 200 to 600 grams at a time from his new source, the coke coming not in powder form but in a hard, crystalline brick—not excessively “doctored up” with baking soda or baby laxatives. Sometimes, depending on how much he picked up, Lenny could see the symbol of the cartel indented in the brick.

He had money in his pocket, a Glock 9 hidden away for protection, and superfluous jewelry jangling from his neck and wrists. He was also dipping into the product with greater frequency, developing a habit that rivaled most of his customers’. He took a leave of absence from school and moved back into the city, holing up with a friend in an unfurnished apartment, his days an alkaloid blur of crushing up product, sniffing, selling, and muting cocaine’s tweaky comedown with heroic quantities of hydroponic pot. Nights rolled around, and Lenny, barely of legal drinking age, was cruising around in limos and spending $2,000 on bottle service. “I used to be the king of Suede,” he says, more embarrassed than proud of this today. It was around this time that he discovered “coke groupies,” quasi-anorexic girls willing to give up any last shred of dignity for a free line. But their presence was better in theory than reality. “Sex is overrated,” says Lenny, “or at least it’s only worthwhile if it’s with a girl you’re crazy into.” One night, he had to take a Viagra just to be able to perform adequately, an experience no 21-year-old man should have to live through.

Lenny was pushing it, he knew. Sitting on the couch in the middle of the day, he’d glance over at his buddy—his sallow skin, the way his eyes had caved into his face, the spastic twitch in his jaw—and some fogged-over cluster of cells in Lenny’s mind would remind him that he was practically looking in the mirror. Then one day he showed up at his apartment and right away he could tell something was off. He walked through the entryway and into the kitchen, taking in the upturned drawers, the broken dishes, the slashed mattress in the bedroom, the clothes all over the floor—it was so surreal that it took him a moment to process that he’d been robbed. His TV and DVD and VCR were gone. So were a pound of marijuana and a briefcase safe with $25,000 inside—the bulk of his life savings. And it wasn’t a random act. The thief had entered the apartment through the roof. Lenny had been targeted. The past few months flashed back like a checklist of how not to run a business. All those nights he tooled around in white stretch limos, just because he could. And the steady stream of nameless girls with Gucci-embossed leather bags prancing in and out at all hours. To say nothing of his own wardrobe of Purple Label cashmere sweaters from Ralph Lauren, Prada loafers, silk-lined Donna Karan motorcycle pants, and the eighteen-karat-gold Cuban necklace hanging stupidly from his neck—$2,500 worth of precious metal practically taunting someone to jump him.

“I blamed myself,” says Lenny, “for being so loose.”

He considered getting out right then. He owed his connection $5,000, which happened to be exactly what he had in his savings account. He could chalk up the burglary as some kind of accidental intervention, pay off his debts, and move on. Or he could get serious: Stop using, keep a low profile, stay in the game another year or two, and cash out. For all the talk of dealers inevitably imploding, Lenny knew scores of guys who owned buildings, small businesses, racehorses—guys you’d never suspect got started pushing product. His indiscretions aside, these had always been his business models.

He reached for his phone, dialed his connection.

“Yo, I’ve been jacked,” he said. “I need you to loan me some stuff, help me get back on my feet.”

Two years later, Lenny is on the move. He climbs the cracked tile steps of an East Village walk-up, delivering a chiquita to a painter who lives in a funky little studio. He’s got a $5,000 watch on his wrist, but other than that, he is inconspicuous, efficient, a pro. From the East Village, he hops a cab uptown—no driving for Lenny; owning a car is “too hot”—and drops off two big ones at an Upper West Side apartment, then another chiquita to an asset-management specialist standing outside an Irish pub in Hell’s Kitchen. “It’s all about the speed getting to each spot,” Lenny explains as he slides into the backseat of another cab, pouring the Baggies into his lap and counting them. “If I’m taking too long, someone will call back and say, ‘I’m gonna call someone else.’ That’s the competition, you know?”

Meanwhile, one of his “partners” is traversing the city making similar stops, staying in constant contact via Nextel. He’ll sell $1,000 worth of tickets tonight, keeping 20 percent of the profits and kicking $800 up to Lenny. Until recently, Lenny always hired other people to do the grunt work, just like in high school. “That way, I’m getting paid,” he says, “but no one’s putting my face to the service.” But these days, since he’s priming his company for auction, he prefers to do as much of the work himself as he can. In a business of deception, finding trustworthy employees is a challenge: A few months back, Lenny caught a worker cutting his Baggies with baking soda, pocketing the extra profits, and pissing off regular customers, which is just the sort of misstep he can’t afford to repeat. He’s already piqued the interest of a few potential buyers and plans to start showing them the spreadsheet over the next few months. (“Honestly, I don’t even know if drug people know how to read a spreadsheet,” says Lenny. “We’ll just have to see.”) Serious prospects will then trail him for a week, to see that the numbers add up. Then he’ll make the biggest deal of his life—assuming, of course, that he is genuinely ready to give up the game.

On the corner of 24th and Sixth, Lenny meets up with two club kids, followed by a bartender at a gay bar farther downtown. Then it’s another cab back to the East Village. He has just shy of 200 regular customers, and the list grows solely by word of mouth: When Lenny gets a call from an unfamiliar number, he asks for a reference, then calls that reference to make sure it’s legitimate. His primary market is still kids in their twenties, many of them new to the city, the majority living in the East Village and on the Lower East Side. But he does not discriminate. Among his regulars are strivers, slackers, black kids, white kids, Asian kids, NYU kids, socialites, agoraphobics, a lesbian couple, an Afghan lawyer, an Ivy League undergrad who deals Lenny’s product on campus, and a Russian “diplomat brat” who lives out of town but comes to New York twice a month to hole up in a hotel suite with his lover. “I’d like to market more in the finance world,” says Lenny. “One guy I know, he’s always telling me to go after that scene, dudes who have no issue burning through $500 on a Friday night. But it takes time. You’re basically saying to people, ‘Tell your friends about me,’ and hoping the message gets to the right people.”

At least 6 million Americans do cocaine every year, making it more popular than 50 Cent’s last album. Ninety percent of the supply comes from Colombian cartels, passing through numerous hands before it reaches Lenny. Because 72 percent of the cocaine comes across the Texas-Mexico border, Houston has emerged as America’s leading distribution center. (The rest arrives by ship via the Caribbean, with a small percentage coming directly from South America.) From Houston, the drug is shipped to other cities hidden in tractor trailers. Once it reaches New York, the supply is controlled mainly by the Mafia and Latino street gangs. Lenny has contacts in both worlds. That way, he can play the two against each other, keeping the price low and quality high. Whenever one supplier jacks up the price, Lenny takes his business elsewhere until the price comes down. “That’s why we call it ‘the game,’ ” he says.

Truly pure cocaine is impossible to come across on the street; most users are so accustomed to sniffing diluted product that pure coke would be too potent to enjoy. A kilo arriving in the U.S. tends to be 80 to 90 percent pure and cost between $17,000 and $25,000. Before reaching someone like Lenny, it’s cut twice to make four kilos with about 22 percent purity, each of which will then generate around $100,000 in street-level sales. (Some kilos are cut up to three times, bringing the purity down to 11 percent, but you can only sell this inferior product in “ignorant” markets—college kids, indiscriminate addicts, etc.) Lenny tests the purity of all his purchases by weighing it, cooking it, then placing it on a triple-beam balance: The additives sizzle away, revealing the weight of the pure drug. “My suppliers are straight with me,” he says, “because they know I’ll know if they start giving me shit. Since I’m making them money, fucking me on quality is not in their interest. So if it’s not that good, they tell me, and I only buy a little to keep them happy. When it’s good, that’s when I stock up, keeping my customers happy.”

Lenny prefers his “mobbed up” connection, because with him, Lenny can run a tab, paying only 50 percent up front. Also, the product is delivered to Lenny’s apartment, allowing him to avoid walking the streets in possession of enough cocaine to put him in jail for 25 years. But sometimes things happen—turf wars, executions—that temporarily pinch the supply and increase the price, at which point Lenny takes a nerve-racking trip uptown, where the cocaine trade is split between the blacks of East Harlem and the Latinos of Washington Heights. According to a report by the White House Office of National Drug Control Policy, Washington Heights is “the primary distribution center for retail and wholesale cocaine and heroin throughout the Northeast,” a fact that comes as no surprise to Lenny, who knows numerous blocks where half the crumbling buildings are fronts for bulk narcotics distribution. Each street has a boss, who employs women and children to do the work, so Lenny ends up buying two ounces of coke from “like a 20-year-old hoochie gangster bitch” who hides the product in her cleavage. “You give her a hug, cop a little feel, deal done,” Lenny explains. A white guy with a private-school diploma can easily become a piñata in this world, but Lenny knows how to behave. “You just have to show up with attitude,” he says. “Basically, you give them a look that says, If you don’t fuck with me this time, I’ll be back. Also, the first few times, I brought my gun. You know, just in case.”

At Tompkins Square Park, Lenny hops out of the cab. It’s well past midnight now, and the street is teeming with scraggly indie rockers, suburban pseudo-punks, and other kids giving new personalities a test run. Lenny hooks up two girls with rigorously straightened hair, then darts into a nearby bar, where he ducks into the bathroom with a graduate student, emerging $200 richer. On occasion, Lenny sells other drugs—pot and Ecstasy, mainly—but he has built his company around cocaine because it’s the most lucrative and, these days, the most in-demand. He could make substantially more selling larger quantities: moving into wholesale, supplying guys like him. But that would mean storing keys in his apartment, and Lenny rarely buys more than half a kilo at a time. He carries much less than that, so that if he’s arrested, his jail time would be minimal, likely just a few days. “It’s like this,” he says. “Whoever I deal with deals with a gang, someone who’s taking the risk of talking to the cartel. I pay a little bit more to stay disconnected from that.”

But staying disconnected from the syndicate level means being more connected to the spontaneous customer, an increasingly capricious contingent the later it gets. As Lenny walks out of the bar, his cell phone rings, beckoning him to a Nolita apartment, where a self-tanned, stiletto-heeled woman insists he kiss her new lapdog before she pays him for her three grams.

“Oh, come on!” she begs.

“I see the dog,” says Lenny. “Very cute. But I’m good.”

“Just a little peck! Don’t be a prude!”

“Sometimes I feel like a vulture, like if it wasn’t me selling it, half my customers wouldn’t be comfortable doing it. At the same time, I don’t create the demand, right? The product sells itself.”

Lenny rolls his eyes, obliging as she rummages through a drawer, searching for her money. The cash is buried under a stack of empty boxes of Lexapro, an antidepressant. Lenny walks out, shaking his head. “It gets mad lonely and depressing,” he says, ducking into a bar and ordering a beer. As he scans the crowd—kids his age, all huddled in groups, faces flushed, enjoying themselves—his melancholy turns bitter. “And here I am, a Friday night, running around like this. Do you see me with friends? No. Do you think I can have a serious girlfriend? Fuck no. How can I have a girl? They say I don’t commit, I don’t give back. Well, no shit. I’m too busy pretending to be nice to bitches like that, coke fiends I don’t even know.”

Lenny sighs, rubs his temples, orders another beer. Sometimes he can’t help but be disgusted by his customers, people living the heedless life he gave up when he “changed from being a consumer in that environment to being a provider for that lifestyle.” But Lenny is a consummate salesman, and to his customers he plays the role of cordial and crooked shrink, supplying all the hollow justifications that once kept his own fears at bay. When clients invite him to hang out, Lenny understands their motives: They need to convince themselves that he is merely a friend who happens to have drugs on him, not a dealer supporting an unhealthy habit. So Lenny chills, sips a beer. Sometimes customers insist he do a line with them, at which point Lenny, who no longer uses, “accidentally” blows out through the straw so the coke flies everywhere, and then laughs it off. Every morning, he wakes up to a dozen missed calls on the Nokia, all delivery requests made between four and six in the morning, all from a few jonesing clients. When he calls back, the customer always plays innocent: must’ve been a fluke of the phone, a mistake of some sort. And at least once a night, a client will hesitate at the last minute, coming down with a case of buyer’s remorse, at which point Lenny is forced to really turn it on. “I’ll sit back and reassure you,” he says. “Like, ‘Listen, I’m not going to criticize you for what you do. If you think you’ve done a lot, it’s nothing compared to what a lot of people do or what I’ve personally done in a week’s time. If you’re really stressed out from your girlfriend and you want to go out all night and have a good time—please, I understand where you’re coming from.’ ”

When Lenny thinks a customer truly is going too far, he will refuse to make the delivery. But even this is a subversive form of business management: “The client that buys a little bit consistently is way better than the client that, like, OD’s and then never wants to do it again.” This Lenny learned from a customer who lived near Union Square. First it was one delivery a week, then two, then three. On each visit, his customer seemed ten pounds lighter. Lenny noticed that the same miserable pizza would sit on his kitchen table for a week straight, clearly the guy’s sole source of nourishment. At one point, he owed Lenny $500 and disappeared completely. “Then he comes back, like, ‘Hi, I went to rehab!’ ” Lenny recalls. “I’m like, ‘That’s cool, man, pay my ass and stay away from this shit.’ I was happy for him. He looked better, was going to the gym. But sure enough, he starts smoking weed again, then doing coke again. And—boom—this time he left the country. Haven’t heard from him since.”

Lenny is not immune to guilt. “Sometimes I feel like a vulture, like if it wasn’t me selling it, half my customers wouldn’t be comfortable doing it,” he says, before reverting back to the entrepreneur’s selective, capitalistic logic: “At the same time, I don’t create the demand, right? The product sells itself. My job is to get the word around, let people know it’s available, and be responsible about making my appointments.” In the end, what’s most difficult for Lenny is admitting that the rush he gets from selling—the instant gratification, the bolstered confidence, the feeling that he’s the nucleus around which everything orbits—is in many ways identical to what his customers call him to experience. As much as he says he is working to sell his business, it’s hard to know if and when he’ll make the move.

’In September,” says Lenny. “I’m out in September.” It’s after three in the morning now, and he is walking along East Houston, past dingy bars serving last call and drowsy-eyed girls in heels and pre-torn jeans. The coke-to-cash ratio in his pockets has shifted, from about 30 tickets and $20, to three tickets and $2,500. A busy night, as predicted. “Or maybe October,” he goes on. “I don’t fucking know. November at the absolute latest. Or I might wait for the holiday season, that’s the hottest time of the year. Probably January ’07.”

Looking for after-work drinking partners, Lenny calls a few friends from high school and a girl “I’m, like, basically in love with.” But no one picks up. “I’m telling you, man, I’m sick of this,” he says. “I hardly go out with anyone, right? And when I do, guess who always picks up the bar tab? Everyone eats off me. Always. They don’t like what I do, but they like what it gets them. Girls act all worried, then ask to borrow my credit card. It’s fucked up, but there it is.”

It’s not that Lenny doesn’t realize how lucky he is. He has no police record, has never had a gun pulled on him, and hasn’t had to threaten violence since he switched to selling coke. But he also knows that everyone’s luck eventually runs out. Some nights, thinking about this, he can barely sleep. “I have nightmares all the time,” he says. “I’m getting shot in the head, or I’m awaiting bail. I shoot people in my dreams no problem, I go on all these murderous rampages. Someone steals $50K from me and keeps saying, ‘I didn’t steal it, I didn’t steal it!’ I have mad issues about trust. I’m sure that if I went to a doctor, I could get all sorts of drugs. Like anti-anxiety or whatever.”

Not long ago, Lenny was on one of his law-school kicks again. He bought a book of LSAT practice tests, turned off his phone, and sat down to see how he would do. They proved more challenging than he expected. So accustomed to being on the move, he hasn’t mastered the skill of sitting still for two and a half hours. He tapped his foot. His eyes darted around. His mind got snagged on more immediate business concerns.

“Thing is,” he says, “every six months I stay in it, I can throw another $25K onto my price. More people talk about me, more people call me, my number becomes more valuable. But then I get there, and I want more. That’s always been my problem. It’s a risk, but obviously there is appeal in that, you know? It’s not like I don’t want to get out. I do. It’s just … ”

But Lenny doesn’t finish the thought. His phone rings, a customer from earlier looking to replenish his supply. A seven-block walk for an extra $60. Lenny shakes his head. “Fuck it,” he says. “Let’s get on that.”