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In 2008, New York City Special Narcotics Prosecutor Bridget G. Brennan began leading a team of undercover investigators targeting the drug dealers who used Craigslist to advertise their wares.

She sounded confident.

“It’s like shooting fish in a barrel,” she told the Daily News. That year, a Citigroup vice president, Mark Rayner, was caught moving ecstasy and cocaine from his Midtown offices using Craigslist. “We see lots of professionals, people with good jobs, doing it,” Brennan said.

Three years later, drug dealing on the classified-ads website is still blatant and ubiquitous.

Sellers thinly camouflage their activity by posting ads for “420 T-shirts” or “tickets to the 420 show,” using the numerical calling card for marijuana, or referring to “Tina,” “T,” and “parTy” for crystal meth. “Snow” or “skiing” is a cocaine reference. “Relief” calls up a healthy section of pills: Xanax, Ambien, Ativan, Klonopin, morphine.

Ironically, no search term is more productive at bringing up drug ads than “law enforcement,” standard words for a buyer or seller who insists he’s not with the NYPD.

Only a man named “Kai,” however, appears to sell heroin openly on New York’s Craigslist pages. And he’s not very subtle at all.

“Want to ‘nod out’? Ride the ‘H’ train,” reads one subject line. The body of that advertisement offered “H, d@pe, diesel” for purchase “anywhere in Manhattan public or private.” Sometimes he throws in the term “Papaver Somniferum L.,” the Latin name of the plant that opium and poppy come from. For good measure, Kai insists in his ads that he’s not law enforcement “and you shouldn’t be either.”

“We continue to conduct investigations into narcotics-related activity on Craigslist,” Brennan tells the Voice. “Clearly, Craigslist and social-networking sites provide new opportunities for drug traffickers. It’s something we’re aware of and continue to investigate.” Craigslist itself, however, did not respond to Voice requests for comment.

On a recent evening, Kai—who asked the Voice to use that name as an alias—finishes up a rack of ribs and a slice of cheesecake at a barbecue restaurant in Harlem. It’s only 7, but it’s been three hours since he last shot up. “I want to use right now,” he says, looking nervous. “I’m thinking of how, I’m thinking of how.” He takes out a cell phone and double-checks the Craigslist ad he had put up the day before, hoping someone will answer it soon. He sells drugs, he says, to support his own addiction, a fact that gets more obvious every minute since his last fix.

Despite the city’s crackdown, Kai says he has gone untouched by law enforcement for the seven years he’s been dealing on Craigslist. In his ads, he lays out strict e-mailing rules for his clients: include only a name and cell phone number. If a potential buyer follows the rules to the letter, he sets up a meeting in a public place—but he arrives without drugs. He says he can tell in a few seconds if a potential customer is legit, but makes each buyer lift up their shirt to show him that they’re not wearing a wire, and lift up each pant leg to show him that they’re not carrying a gun. Small talk builds to questions about drug use and then to specifics like quantity and price. Kai says he doesn’t negotiate.

When Kai and his customer have agreed on a price, he makes the customer wait on a corner while he goes to pick up the drugs from a “stash house.” The hand-off with the customer occurs back on the street. He says he tries to accommodate unpracticed buyers by hiding the heroin, “like in an empty cigarette pack.” Then he circles back to the stash house to buy his own fix.

Kai estimates that he introduces 10 percent of his customers to the drug for the first time, almost all of whom he says are graduating from addictions to other opiates.

He looks dumbfounded when he’s asked if anyone he introduces to the drug doesn’t like it: “It’s heroin!”

Selling drugs on Craigslist is less fraught for “Andrew,” an Adderall dealer. First of all, he’s not a heroin addict. The 30-year-old Queens resident and former “Tina” user trolls Craigslist with ads that offer “study aids” and “concentration tools,” and finds a bigger market than Kai for a drug that people perceive as less illicit.

[Using the same keyword searches that turned up numerous drug ads on Craigslist’s New York City pages, we found only a single ad, in several variations, offering illicit drugs on local pages at The Backpage ad was repeatedly flagged and taken down, and reappeared over several weeks. is owned by the same company that owns The Village Voice.]

While Kai says he’s “lucky to make $100 in a day,” Andrew claims to sell about $8,000 worth of Adderall every month, but only clears about $2,000 in profit. He says that his clientele is “60 percent female,” made up of “mostly students and professionals between the ages of 23 and 45.” He suspects that many of his customers use the amphetamine as an appetite suppressant.

“I guess the idea came to me when I was on the site constantly looking for a job,” Andrew says with a hint of frustration in his voice. He moved to New York eight months ago and has been unable to secure steady employment despite his college degree.

He says a friend of his offered to pay him to get an Adderall prescription from a doctor and supply him with the pills. When he realized that what his friend was doing was lucrative, he turned around and enlisted some of his own friends to do the same thing. He sends them all to the same “cool doctor,” who is both loose with the pen and “actually cool.”

Like Kai, Andrew also claims that he has never been caught on Craigslist, although his friend who got him into the Adderall trade was arrested in a sting. His friend still sells Adderall on Craigslist, and Andrew seems to understand the risk involved: “You think he’d be, like, once bitten, twice shy. But he’s not.”

Another Craigslist dealer, “Maleek,” also says he was caught in an NYPD sting. He sold prescription opiates to an undercover cop on four separate occasions, and the officer would never get out of the van he drove up in. “I thought that was normal; I was very naive then.” He says that he paid his bail with the money he’d earned selling pills, and completed a program intended to reform nonviolent drug dealers instead of serving jail time. He still sells drugs on Craigslist, but has downgraded from Schedule I narcotics to the muscle relaxant Soma and the painkiller Tramadol, which are not controlled substances and carry diminished penalties.

In a Midtown bar on a Tuesday afternoon, Andrew downs three beers, a cocktail, and a shot within an hour, but is still speaking quickly and gesticulating with a vigor that indicates, like Kai, that he may be dipping into his own supply. He says that he has to go meet a customer, and then he goes into the bar’s bathroom to wrap 10 Adderall pills, totaling $200, in the plastic wrapping of his cigarette pack.

On the walk west through Midtown to meet Andrew’s customer, he reveals some tricks of his trade: to stifle competition, “Dealers flag other dealers’ posts.” If a post is flagged for removal enough times, it is automatically taken down. “Sometimes posts are only up for five minutes before [competing sellers] get to them,” he says. He adds that he personally never flags other dealers’ posts.

Andrew says he also checks potential customers’ Facebook profiles to make sure they’re legitimate before he meets them, reasoning that an undercover cop wouldn’t go to the trouble of creating a fake Facebook profile and adding hundreds of “friends” just to catch small drug-dealing fish on Craigslist.

He meets his customer in the Chipotle restaurant on 37th Street and Broadway. She turns out to be a voiceover actor who speaks with a similar speedy intensity and swears a lot. She theatrically delivers the voiceover from a commercial for a household cleaning product, suggests that she and he hang out some time, and then heads back to work.

Later on the same afternoon, with Andrew on to other business, Kai describes his plight on a bench in Manhattan’s Morningside Park. He is clean-shaven, dressed in jeans and a black peacoat. His hair is cropped close on the sides, combed forward, and flipped up in the front like a schoolboy’s. He speaks with clarity and enthusiasm, especially about heroin. “If there’s one thing you can do every day, that you can fall in love with ritually and romantically, it’s this.”

He says he has been addicted to heroin for 13 years, since attending an elite private university in Boston. He pulls up his sleeve to reveal his tracks, the series of scabs, scars, and black-and-blue marks lining his veins between his forearms and his biceps. At moments during long spells of conversation, he scratches at his chin and neck. When he does, he pulls the high neck of his cashmere sweater down slightly, revealing a glimpse of his hidden skin, which seems like it should give away more about his destructive habit. Asked if his turtleneck is meant to cover up tracks or scratch marks on his neck, Kai insists the sweater is just warm. “And stylish,” he smiles.

But he concedes that his put-together appearance is the only thing in his life that’s “not a mess.” He doesn’t remember the last non-drug, nonessential item he purchased or the last movie he saw. He says he went to prison for heroin possession in 2003, and again for “dirty urine” three years later, but not for selling on Craigslist. He teases that most of the other people who looked like him in jail were there for “computer crimes.” He chuckles when he says this.

Since getting out, Kai’s business has been steady and uninterrupted, but he hasn’t exactly built a lucrative hustle over the years. “Customers go to rehab or disappear,” he says. And regardless, “All my profit goes back into my vein.

“I’m not the guy going to buy a Beemer and going to shop all day in Soho. I’m the guy who’s doing it to support my habit. I am so far from the pimp daddy, American Gangster dealer,” he says, sounding nerdy enough to rule out “rock star” as well. Selling and shooting up, he says, “have no effect on making me feel like a badass. It doesn’t give me a swagger or a jolt in self-esteem. It doesn’t make me feel cool.”

Though Kai can’t afford to always be carrying drugs, he always has his supply kit, including about 10 fresh needles, a bag of tiny cotton balls (each about one centimeter in diameter), three non-matching bottle caps called “cookers” (obviously taken off soda and beer bottles), a large rubber band called a “tie-off,” Band-Aids, alcohol swabs, and tubes of purified water. It’s all free and comes from a public needle exchange in New York City that exists to prevent the spread of HIV. Kai picks up supplies there about once a week.

The needle exchange also grants him some degree of legal immunity if he is caught with the paraphernalia; one night, he overdosed, passed out on the subway, and woke up in the hospital. When asked why he wasn’t arrested, he responds by taking out his needle exchange ID card. Kai says he would never share a needle; he is HIV-negative and gets tested every six months.

He also notes that he doesn’t like other people touching his kit. Despite having an addiction that many think of as dirty and excessively risky, Kai is obsessive about germs and claims to look out for his health. He is an avid walker, says he eats mostly fruits and vegetables, and takes an intense regimen of health supplements. “I take a multivitamin, a calcium-magnesium supplement, a B-vitamin supplement, omega-3, 6, and 9, choline, inositol, an amino-acid tablet, vitamin-C supplements,” he explains. “It’s for my general well-being.”

At the restaurant in Harlem a few days after our initial meeting, Kai uses the salt shaker from the table to demonstrate the amount of heroin that comes in one “bag,” a tiny, taped-off piece of wax paper, each of which he sells for $10. The salt pile is about the size of a dime. Ten bags, or a “bundle,” can fit in one needle, Kai says. He perks up and begins speaking excitedly about the process of shooting heroin. He mimes the motions of preparing his injection at the dinner table like he’s conducting a symphony. Each movement looks precise. Now he really wants to use.

“I have to either call these ad responses from Craigslist and go through that process, or I don’t know. . . .” his voice trails off. He starts to scratch his neck again. “I’m wondering why certain people didn’t e-mail me back. Is it a sign that they don’t want anything or that I should try contacting them?” On his phone, a “burner” that he switches every few months, Kai shows a response from a new potential customer, Jared. Kai notes Jared’s Long Island area code and praises his e-mail. “Straight to the point,” Kai says. “His name and his number. He says nothing about ‘What do you got?’ or ‘How much?’ ” He nods approvingly. “That kid, I might call back.

“It might take him a while to get here,” he worries. “And one thing about Craigslist: People will blow you off.”

A few minutes later, Kai is keeping warm in an ATM vestibule near the restaurant and waiting for a customer to contact him. He pulls a scrap of paper from his wallet. On one side, typed neatly, is a list of names, bold and underlined, alongside a list of phone numbers, presumably regular customers. Kai scribbles a new number in black pen on the other side. He calls Jared from Long Island. No answer. “Jesus, Jesus,” Kai mutters to himself. “What to do, what to do.”

“If I had unlimited money, I’d use it five times a day,” he says. On most days, he’s lucky to get high twice. Running on empty from the day’s first fix, he fiddles with his phone, waiting for contact from any buyer.

“I don’t like to push,” he says. Customers usually come to him. After another unanswered call to Jared, Kai goes for an 83-block walk to kill time as he waits for someone to call. Eventually, he goes home with nothing.

One customer who did come to Kai was “Mike,” a six-year intravenous heroin addict who teaches at an Ivy League university. The two met through a heroin sales ad on Craigslist, and Mike has since become Kai’s part-time partner.

“He’s the only guy I hang out with,” says Kai, and Mike counters, “He’s the only guy I hang out with!”

Despite his bond with Mike, Kai calls his business-and-addiction cycle a “lonely, bleak existence.” He grew up in an affluent suburb of New York, but says his “real friends” won’t see him while he’s using. Aside from family members and heroin suppliers, he met every single person he currently knows through Craigslist, and therefore through heroin.

Beyond Craigslist, Kai calls himself “Internet-savvy” and keeps up a presence on Facebook and Twitter. “For friends and family,” he says, but cautions, “What I’m doing most of the time, they don’t need to hear about.”

In addition to advertising his services as a seller online, Kai uses the site to seek companionship, based not around dating or sex, but drugs. “Run and dream with me through fields of opium poppies; feel their seductive, euphoric kiss,” reads one of his pleas for heroin-based companionship.

Kai explains that among junkies, friendship never includes gifting or even sharing drugs. Kai claims he has slept with customers, recently a stripper, and one of his customers became his girlfriend for several months. Andrew, the Adderall dealer, says he was offered “help downstairs” in exchange for Adderall, but turned the offer down because the woman was “trollish.” He also had an ongoing fling with a customer, which he says began after he advised her to “split the pill in quarters” because she was “really skinny.” Maleek, the opiate dealer, says customers have stripped for him and given him massages.

But Kai states flatly that he would never exchange drugs for sex. “I just don’t do that,” he says. The same goes for buyers, even regulars, hoping to pay later. “Giving a crackhead credit? Forget it,” he laughs, paraphrasing the Notorious B.I.G. “You’ll never see the money.”

Two days after dinner with Kai at the barbecue joint, he and Mike go to the needle exchange in Manhattan. It’s the afternoon of Kai’s 33rd birthday, a day that will pass like every other. Kai has convinced Mike to join the needle exchange, if only to save a few dollars per week on supplies. On the walk there, Mike, like Kai, is surprisingly comfortable telling his story in intimate detail, stopping only occasionally to fret about his anonymity. Also like Kai, Mike asks that certain details about his life be left out, for fear of being recognized by friends, family, or business associates. More often than not, both just seem happy that someone is listening.

Asked how he imagines a newspaper story might affect his business, Kai says he thinks it will lead to greater exposure for the heroin trade on the site, but that Craigslist might soon be flooded with heroin of dubious quality. Upon further reflection, however, he says he will probably lie low for a while.

He doesn’t account for the business he might miss, but says that he hasn’t held a legal job since 2007. Since his sales only cover his own drug use, Kai relies on food stamps and unemployment insurance to eat and Section 8 government assistance to pay rent. “I never have cash sitting in my pocket,” he explains, despite selling every day. “It sucks, right?”

Mike, on the other hand, has his university teaching job. He scored over 1500 on the SAT, played on an all-state sports team in high school, and grew up in an upper-middle-class suburb. Except for his $100-a-day heroin addiction, he says his life is going well, and he has plans to pursue further education. Mike says that his girlfriend and parents know that he has a history with heroin, but don’t know that he still uses it. “My girlfriend thinks my tracks are old.” When we ask Mike where his girlfriend thinks he is right now, he shrugs and says, “The library?”

As we near the needle exchange, Kai and Mike confer about whether to meet a new customer who has just e-mailed via Craigslist, looking for $50 worth of heroin. The customer says that he’s only willing to meet near his apartment on Canal Street, which strikes Mike as fishy. “He says he’s dope-sick and he can’t move, so that’s why he needs to meet there,” he says with more than a hint of doubt in his voice. Kai nods in agreement and says, “It’s suspicious.” They note that anyone who is dope-sick would be that much more motivated to move to wherever he can find a fix, rather than making an unwavering demand for a delivery at a specific location. They both say that they wouldn’t even be considering a transaction like this if they had a choice, but Kai and Mike need to score today, too.

Before the duo reaches the needle exchange, the customer relents and agrees to meet at Union Square, so Kai and Mike decide on a location and then e-mail the customer to give him the go-ahead.

Ten minutes later, in a sweltering basement office lined with cubicles, fluorescent lights, and hopeful posters reminding patrons not to contribute to the spread of HIV, Kai receives a fresh bag of supplies from the city. Mike signs up and receives a bag of supplies, too.

Walking to the subway downtown, Mike remarks that he’s found a buyer for a pair of headphones he has been looking to sell on Craigslist. But a problem crops up as soon as he emerges from the train: The person trying to buy the headphones needs them as soon as possible, and the heroin customer is still in a cab on his way. Mike and Kai split up, with Kai pretending to be Mike on a phone call to the headphone buyer, while Mike goes to the chosen meeting spot to find the heroin customer.

Kai tells the headphone buyer that he is running late, but will be at the corner of Bleecker Street and Broadway very soon, and then he finds Mike, who by this point is already in the process of “feeling out” the heroin customer. Kai keeps an eye on Mike and the customer from a distance, staying about 30 feet behind them, watching them as they duck into a covered driveway, exchange the heroin and money, and split. The customer looks barely 21 and is dressed in a bright-blue hooded sweatshirt.

“There’s no stereotypical junkie,” Kai insists. “If you saw the array of people I deal with, you wouldn’t believe it.” He counts “people who pay their mortgages on time,” including an ob-gyn doctor and two middle-school teachers, among his customers. But he even compares his appearance with his conception of a stereotypical dealer: “You see my ads, and you think you’re gonna meet some big African-American gangsters. But it’s just me!” He points to himself and laughs.

On the corner of Bleecker Street and Broadway, the man buying Mike’s headphones asks him why he’s selling them. He says, “I need the cash because my rent is due in about a week and I’m short,” which would place the due date of his rent well into April. The man doesn’t seem to notice, and he hands Mike a $50 bill. Mike holds it up to the sunlight to inspect it. He and the buyer shake hands, and then the buyer walks away. We wish Kai a happy birthday as he and Mike set off for the stash house.