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.