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The Bootleggers

One night in the life of two street hustlers

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A dark, dirty bit of sidewalk outside a south-side Red Line station doubles as the office of Chris and Henry*, partners in a small-time bootleg CD hustling operation. It's ten o'clock the Friday night before Independence Day and scraggly fireworks blossom over the roof of a high-rise across the street. The bootleggers are planted between the Plexiglas station doors and the bus stop at the curb, barking at strangers making their way to the train. "Get your Lil Wayne get your Young Jeezy get your R. Kelly while it's hot! Cheap CDs, cheap CDs, cheap sex--I mean cheap CDs!"

A tomboyish girl steps off the bus and looks around uncertainly, hugging her backpack. There's a cluster of guys hanging while Chris and Henry work, most of them friends and acquaintances of Chris's. He affectionately calls them the "white T-shirt posse" since they're all in big white T-shirts. "It's kind of like a camouflage for when the cops come around," he says. A couple of his friends are hustling too. One hands out glossy postcards for a tattoo parlor, another sells "squares"--single Newports from the carton--for 50 cents.

"Two for five, five for ten!" Chris sings, and the girl sidles over. "What you got?" she asks softly. She's the night's first customer. With a friendly nod Chris directs her to Henry, who stands in a dark corner under the station's steel roof, rolling a messy cigarette with one hand and checking his phone for texts from his girlfriend with the other. At 32 he's almost ten years older than Chris and has his own name for his partner's friends: "the degenerates." He's in wrinkled khakis and a worn plaid shirt, a duffel bag hanging around his ample waist. He sticks the cigarette between his lips, unzips the bag, and pulls out a stack of jewel cases. The girl takes a handful and turns away, silently reading the track listings.

"That's a fabulous collection right there," Henry says politely. His dark eyes, behind thick glasses, are shadowed by the brim of a baseball cap. She doesn't respond.

"No--that's a fabulous collection right there!" Chris shouts as a woman in tight pink pants walks into the station. His friends burst into laughter and trade insults about who spends the most time masturbating. "We call Henry 'Obi Hand Kenobi' down here," says Chris. "You can't love someone till you love yourself," Henry shoots back. The girl hands over three dollars for a Lil Wayne album--the summer's hottest seller by Henry's count--shoves it in her backpack, and saunters down the sidewalk.

Between the sales pitches, insults, and catcalls, it's never quiet at the curb. Henry has a little battery-operated CD player propped up on a trash bin, bleating out a new Kanye West mix he's selling. Joints and plastic bottles of liquor emerge from back pockets, and pretty girls constantly drop from the crowded buses lurching up to the station.

Sudden shouts explode from a nearby liquor store. Three guys run out, swing into a rusty car, and peel off. Chris hollers, "If some of you ain't seen your cousins in a minute, you can find 'em at county tonight!" Henry rolls his eyes. He kicks away a burger wrapper and sits down heavily on the sidewalk, shaking his head as the white T-shirt posse whoops and high-fives at the getaway.

This is Henry and Chris's third summer working together. They met outside the station, where Chris was already hustling. He'd started selling squares after dropping out of community college at 21, four semesters shy of graduating, because his girlfriend at the time was pregnant. He's not sure why they're called squares. "Maybe it's because of the square box," he says. "Maybe, if you have to ask, you might just be one." He says squares are a gateway product for lots of hustlers--squares to bootlegs to weed to harder drugs.

Chris picked this spot partly for what Henry calls its "structural advantages." It's easy to keep an eye out for police coming by car or on foot. It's not foolproof; Henry was caught with a few hundred CDs by an undercover cop last summer and spent a few days in lockup. Chris's CDs were out of sight, so he pretended not to know Henry and walked off like any casual witness. Henry could have faced a $100,000 fine and three years in jail, but the charges were dropped for lack of evidence that he was actually selling the CDs. Chris has been hauled in three times for bootlegging, but he says nothing ever stuck and the most he's spent in lockup is half a day.

Chris's merchandise is stashed downstairs, in the CTA booth by the turnstiles. He says he's made friends with all the guards; they exchange friendly hellos with him throughout the night. "See, they know that it's to their advantage to keep me around," he says. "'Cause when I'm here, no one's gonna try to start any bullshit." He bobs and weaves like a fighter while he talks, elbows up and knees cocked. The white T-shirt posse laughs, but no one contradicts him. "Security, they get paid by the hour, they don't give a fuck about me selling on CTA property. If nobody gets hurt, they don't have to do anything."

A boy of maybe 12 wheels up on a red BMX, pulls out a roll of singles, and waves it under Chris's nose. "Baby hustler," Chris calls him. "These kids ride the train asking for money for their basketball camp or whatever. There is no basketball camp, but there is this bike over here." The boy smiles, suddenly shy, and hides behind Chris's broad back, peeking over his shoulder and fanning out the wad of bills.

Chris takes a slow drag off a Newport, leans back, and blows the smoke over his friends' heads. "Everything you see here, I built this from the ground up," he says, sweeping his palms over the sidewalk, dark with old gum and tobacco spit. "There was nothing here, and now look. It's like a community sprang up. We are here for the people, man. We're like a nonprofit organization."

Henry breaks from rapping Jay-Z under his breath and shoots Chris a look. "Might as well be nonprofit, at two for five."

Two summers ago, right around the time Chris upgraded from squares to CDs, a hustler friend who'd recently gotten out of Stateville agreed to teach Henry how to bootleg. Henry had just been fired from a pizzeria and decided to end the long string of boring, low-paying line-cook and cashier jobs he'd held through his 20s. He started out working buses and busy north-side stations. Looking for a vacant spot to make his own, he rode up the escalator at Chris's station one Friday night, introduced himself, and bummed a cigarette, expecting to talk trade for a few minutes and move on. He'd heard stories of territorial bootleggers, especially on the west side, who'd get violent with competition that lingered too long. But Chris drew him in, extolling the advantages of the location, and suggested Henry start selling there too.

"Me and him, it's like we're intertwined at the hips," says Chris, pressing his palms together hard, knotting the fingers. "We both love weed and we love women." Chris figures he smokes a dozen joints a day, significantly less than Henry, but they're usually high while they work. Chris turns to give his partner an affectionate smile, but Henry is shuffling down the sidewalk along the overpass, his duffel bag swinging heavily at his waist. "Bathroom," Chris says, shrugging. "That's the only thing he walks away for. Pop and piss. The two Ps, the fundamentals. Oh, and pot. Me, I also believe in the three Bs: beer, blunts, and burgers. Get high, get head, and go home. The necessities of life. This is why me and Henry go together. We believe in the simple things."

Henry and Chris have an arrangement. Twice a week Henry calls up Ernie, a forty-something Latino he met through his friend who was in Stateville. Ernie sells first-generation bootlegs--copies made from legal pressings--from the back of a painter's van. Henry has no idea where Ernie gets them. "He's got his own bootleg man," he says. "I don't know who that is, and I don't want to know." Their conversations are short. Henry asks, "Hey Ernie, can you come out and play today?" and Ernie names an intersection, usually somewhere along Cottage Grove. Ernie then picks Henry up and drives around while Henry flips through the CDs in milk crates stacked to the ceiling in the back. "Early-90s party mixes are the big thing right now," Henry says. "Jagged Edge, Silk, Brownstone." He's also looking for bold cover images and tidy track listings that will reproduce nicely on a photocopier. "That's how you know a novice bootlegger," he says. "There won't be a cover image. There might not even be track listings, and if there are, they'll be all spelled wrong and out of order, or even just inaccurate. Then you can bet the CD won't play right either."

He buys 30 to 50 CDs at a time from Ernie for a dollar apiece and brings them back to his apartment on the north side. Since neither he nor Chris owns a computer, Henry and his girlfriend of two years make copies on a stand-alone CD burner and Henry photocopies the track listings and covers at an employment-resource center nearby. He says the employees there probably think he's working on his resume. "You're supposed to be copying documents for your job, and, goddamnit, this is my job!"

Chris, who's perpetually between addresses--he lives with family members, girlfriends, ex-girlfriends, and sometimes on the el--comes over to Henry's place with a stack of 100 blank CD-Rs from Micro Center, which they've found to be the cheapest source. Chris gives 50 of the CD-Rs to Henry as his share of the cost for Ernie's bootlegs and burns the other 50 to sell himself.

Henry and Chris say they each make $700 or $800 a month, moving the most product the first and third weeks of the month--paydays--and the least right before rents are due. Henry does most of the grunt work, but Chris says he pulls his weight. "See, the way I see it, I'm the attraction of this operation. I'm friendly with people, I build up the relationships that keep them coming. When people like you, they want to spend their money on you. Henry is the abacus, I am the mouthpiece. I bring the people, he counts the change. Without one, there is no other."

Around 11 PM Henry shuffles back to his corner post. The folks getting off the bus aren't in work clothes anymore; they're dressed up to go out. A short guy in a hoodie with a skeleton printed down the front runs up the escalator, laughing hard. A very drunk woman downstairs wet her pants and he saw her do it. The white T-shirt posse laughs. Henry stares. "What does this have to do with money?" he says to no one, with a dismissive nod. "If it's not about money, then I don't care."

A little bottle of Hennessy emerges from the waist of someone's jeans and makes its way to Chris. He catches a hard glance from Henry and waves off the liquor. "Henry won't let me drink anymore," he says, looking a little sheepish. One night last summer, Chris got belligerently drunk, started a couple fights, then passed out inside the station doors. A little later, Henry got jumped by three guys. They took two CD players, three cartons of cigarettes, and nearly 300 CDs--about $1,000 worth of merchandise. Henry refused to work with Chris for weeks afterward, giving in only after Chris swore not to drink on the job. Henry's girlfriend never forgave Chris, though, which is why Henry's apartment is no longer on the list of places Chris can stay.

Between getting arrested and jumped, Henry doesn't like being at the curb late. He'll head home as soon as he's hit his Friday-night target of $75. Chris will stay out on the curb until about 3 AM. "Henry is strictly business," he says. "I'm mostly out here to have some conversation with some girls, look at some nice derrieres, do the hustle on the side. I'm just in this till I go back to school anyway." Chris's plan is to go back next year and become a registered nurse; he's already a certified nursing assistant, though bootlegging is his only job right now. "Henry is overqualified for this, mentally. He may have gone to retard school, but he is in fact a very intelligent individual. Which reminds me--Henry, did they let you use normal forks in retard school, or did you eat with your hands, like animals?"

Everyone goes quiet in expectation of a good comeback. "Sporks," Henry replies, affecting an aristocratic whine. "They gave us sporks. Part spoon, part fork." Chris grins, but it's not the slam-dunk insult everyone else wanted. The other guys turn to flirt with a group of giggly high school girls filing past. "See, that's Henry," says Chris. "He tries to talk to you and it all goes right over your head. People out here don't know how to react to that."

As a kid, Henry was in and out of foster homes, and right before high school he was diagnosed with a learning disability and put onantidepressants, which he still takes. Freshman year he was sent to a special-education high school and the kids in his group home picked on him about it. He struggled to bring his grades and behavioral marks up, and by junior high he was back in a mainstream school. He still sees a therapist, and he gets nearly $800 a month in disability for a heart condition, diabetes, and depression. Between his and his girlfriend's disability payments and his bootlegging money, their rent and bills are covered.

But Henry wants this to be his last summer out on the curb. He's taking classes to become a real estate appraiser and figures he'll make $700 or $800 a week doing that. The licensing exam makes him nervous, though. Written tests have never been his strong suit; he didn't get his GED until he was 21. It won't be his first try at a real career, either. In his early 20s he was accepted at a culinary school, where he did well at hands-on tasks but not on the tests, and he left after a year and a half without a degree. Now he wants a tutor to help prepare for the real estate appraiser's exam, and though a welfare-to-work program he's enrolled in gives him some money for one, he says it's not nearly enough.

A little after midnight a security guard who's friendly with Henry and Chris finishes up his shift and struts out the door, his uniform shirt unbuttoned to reveal a clean white undershirt. The guys on the sidewalk make space to let him pass as his ride pulls up to the curb. "Hittin' the clubs man?" Chris calls. The guard grins slyly, not saying a word, and the guys whistle their approval. Leaning back against the car, he nods at Henry. "When are we gonna see you come in for a form?" he says. He's been trying to get Henry to apply for a job. A couple of the guys start in on Henry too. "Man, would you go in and fill out that form? Grown man with his ass out here on the street, like a thug." Henry avoids the guard's eyes, flicking threads of tobacco from his shirt, and mumbles, "Soon, soon." Between his weed habit, he says later, plus a growing reliance on Vicodin he was originally prescribed for back pain and his difficulty with paperwork, he doubts they'd take him. The guard shakes his head, laughing, and slides into his friend's car.

"Man, fuck being a security guard," Henry says, watching the car charge down the overpass. "Anyone can be a security guard. Fuck tests. There ain't no tests in real life. No geometry, no pi."

Chris slaps Henry's stomach. "That's right, Henry, just apple pie." The white T-shirt posse explodes into laughter, and the smell of weed wafts on the warm air under the station roof.

Henry leans over the curb. "There ain't no pi in life!" He's almost shouting.

"Just blueberry pie, sweet potato pie, apple pie," Chris sings. "There ain't no pi in life."

Art accompanying story in printed newspaper (not available in this archive): Photographs by Jim Newberry.

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