Credit: Frank Okay

Weedman’s workday began as the sun set on a clear December day. He jumped behind the wheel of a nondescript vehicle to start the night’s deliveries: $60 baggies of dry cannabis flower containing an eighth of an ounce each of strains with names like Black Cherry Pie, Cheesy Rider, Wedding Cake, Zweet Inzanity, and Gelato #45; a Mason jar filled with $10 pre-rolled joints; $20 packs of THC-infused gummies, chocolate bars flavored with raspberry and Himalayan salt, and bottles of tinctures.

If you saw Weedman on the street, and someone told you the guy sells weed, you wouldn’t be surprised. But you’d never pick him out of a crowd as the obvious dealer either. Dressed in a Bulls beanie and a puffer jacket, Weedman has a relaxed and confident manner. His sneakers hit the sidewalk at just the right pace. He’s a rare example of a man about midway through life’s journey who both projects total confidence and puts you at total ease. He leans Bob on the Jay-to-Silent-Bob spectrum. He is the opposite of creepy. He has the thoughtful, measured speech befitting a cannabis purveyor. When he says herb he pronounces the H.

His first customer was a white man in his early 20s with scruffy hair and a beard who emerged from a courtyard apartment building in Lincoln Square and got into the back of the car. He wanted tinctures. These are liquid concentrates of THC: a few drops under the tongue can get you high faster than an edible and keep you high longer than a joint. It’s $60 for a 600 milligram bottle. “Can I spot two joints?” the man asked, drawling the vowels à la Keanu Reeves in Bill and Ted’s Excellent Adventure. Weedman obliged. The man was a regular, so they briefly chatted about Weedman’s upcoming holiday road trip to the south, and wished each other well as he exited.

Weedman wasn’t concerned that someone might notice the traffic in and out of his car and call the police. “I don’t think the cops would even entertain it,” he said. “I’ve had friends call 911 to get an ambulance sent over to them and they had to call three times because the cops didn’t believe them . . . there’s people getting killed in this city left and right.”

Weedman’s customers are more often women than men. Most of them are white-collar types. There are a few lawyers and a lot of teachers. Some work in media or advertising, others sell medical supplies. He once had a client who made sets for Sesame Street.

The rhythmic sounds of Afro Medusa pulsed through the speakers as Weedman drove west. He pulled up next to an apartment building in Logan Square and parked in front of a fire hydrant. “Cops in Chicago don’t give a shit about this,” he explained in response to my perplexed look as he exited. “What are they gonna do? Give you a ticket? That’s fine.”

Ten minutes later he settled back behind the wheel. He was amused that the customer’s parents were there, visiting from North Carolina. “His dad bought the weed for him. He was like ‘Ooh the Afghani, we’ll take that!'” Weedman said in a creaky voice imitating the older man. “That’s one of the weirdest things I encounter. Americans are super casual about pot. White American people. The Hispanics that buy weed in front of their parents—that’s very unusual.”

Weedman’s been running his underground cannabis delivery business since the early 2000s, selling dry bud and THC-infused products sourced from growers in Colorado, California, and the Pacific Northwest. His clients text or call him to order, and he usually swings by later the same day. The legalization of recreational cannabis in Illinois is meant to put guys like Weedman out of business. But he’s not worried. In fact, he predicts he’ll thrive and perhaps even attract new customers as more people feel comfortable with cannabis. He’s also banking on the loyalty of his customers, their commitment to what he represents. While some might appreciate the anonymous consumer experience of buying weed at one of Chicago’s dispensaries, Weedman’s services cultivate a human connection that the Walmartization of cannabis could never replace. A person’s relationship with their dealer is one of mutual trust and vulnerability and offers as much of a respite from the grind of daily life as the intoxicating power of the herb itself.

Weedman’s longevity in the underground delivery business is unusual, according to him anyway. No city or state data offers a statistical perspective on the prevalence of services like his or the frequency of such dealers’ apprehension by law enforcement, but Weedman’s seen many competitors come and go over the years. His place in the cannabis ecosystem is somewhere on par with artisanal coffee shops. He’s the $4 latte on the spectrum between Dunkin’ Donuts and owning your own espresso machine.

“There are businesses out there that are way more brazen than I am,” he said. “A lot of rich white kids in this game, they sell stuff on Instagram.” These people tend to get caught for making stupid mistakes, he said, like flaunting their money in front of too many strangers. Meanwhile, street dealers work with lower-income clients and sell herb in packages as small as a gram, often sourced from Mexican cartels or other criminal organizations. “[Dealers] on the street usually buy from a guy who has an army of people,” he said, explaining that they often get caught because they’re working in neighborhoods oversaturated by police. These dealers’ supply chains also tend to be long and include a lot of middle men who may cut and mishandle the product. “With me, you’re probably one or two steps away, at most three from the main source. In some cases you’re the third person touching [the weed]. It’s the grower, me, and then you.”

Weedman’s carved out a safer space for his work. He operates at the intersection of his own sound judgment and neighborhoods with sparser policing. He describes himself as “cruising like a mouse in a field, just moving along. Or moving under a ledge—nobody sees you, you’re just chilling, hiding in plain sight.” He stays off the Internet and keeps his business to strictly weed: “I’ve never sold anything to anybody to put up their nose.” He only works with customers referred by people he trusts. Weedman buys herb from growers at wholesale prices usually ranging from $1,000 to $2,500 per pound. Sometimes he gets it delivered through the mail. “It just needs to be packaged really well,” he said. “Just like any other smuggling it needs to be sealed and not stinky.” Other times, he or someone he trusts drives it from the western states.

“If I’m driving it I’m going for the gold,” he said, meaning he buys up to 40 pounds of dry cannabis flower at a time. The weed gets secreted away inside inconspicuous vehicles, but since the consequences of getting caught transporting it over state lines would be severe no matter the quantity, “I just take as much as I can drive.” He never buys more than he can afford, though. He’s seen people take out loans to buy enough product to fill a semi truck and then have trouble selling it all and paying back creditors. “A lot of bad stories with debt.”

If he’s driving with his supply, he has a plan for how to deal with the cops if he’s stopped: “Never be in a rush, that will save you eight times out of ten.” The second rule is to never talk to the cops. “If you’re being stopped doing what I’m doing, you’re already being caught,” he said. “Your best bet is just to shut the fuck up.”

Weedman smokes his own inventory and sometimes worries about getting pulled over and called out on smelling like weed—which cops in Illinois will still be allowed to use as probable cause for a vehicle search despite legalization. But he’s also got a medical marijuana card and, if questioned, he’d just admit that yes, he had recently smoked. (Determining cannabis intoxication is notoriously difficult, but, according to the Chicago Police Department, no new field sobriety tests for figuring out if someone is high have been added to the existing DUI investigation protocol.) If he’s pulled over with his daily delivery supply, Weedman has a lockbox to throw his stash into. He’d refuse to open it if asked. “They can’t make me open it without a warrant,” he said. “And I would be ready to go to jail over not answering cops. They’d have to book me for who knows what, come up with a crime for me on the spot—they would have a hard time getting into that box.” Weedman has a lawyer. He declined to comment on whether he’d ever been busted before.

Weedman avoids texting too many details and talking too explicitly on the phone. His competitors often work with menus and when clients text, the dealers send back a list of what’s available. Customers have to make specific orders and then get only whatever they asked for delivered. Weedman operates more like the Avon lady and brings his entire day’s supply to every customer to let them peruse in person.

“People will be psyched about the dispensaries, but then I think people will call me back,” Weedman said. “Because of the prices.” At $60 for an eighth of herb, his prices are on par with what dispensaries charge for medical cannabis, but he’s sure that recreational pot will be more expensive—especially because demand will soar and supply will be limited. The state has warned that recreational dispensaries will run out of product quickly in the new year. Since the dispensaries will only be able to sell pot grown in Illinois and it takes a few months for a plant to mature and produce optimal bud, Weedman will be there to fill the void with his fully operational year-round supply chain. He’s been getting ready for months, “just stacking [one-pound] units, waiting for the dry spell.” He predicts that the recreational dispensaries will be “more for the guy who comes from Indiana with his friends.” Plus, he has a satisfaction guarantee. If someone finds something wrong with his product, or even just doesn’t like the taste, he’ll replace it for free. Even if the customer has already eaten all the gummies or smoked all the herb.

Another edge he’ll have on the dispensaries is that he’s able to sell much more potent products in larger quantities than will be permitted under the new Illinois law. While he can sell you as many $40 chocolate bars with 200 mg of THC each as you’d like, the dispensaries will only be able to sell 500 mg of edibles at a time. For people dealing with chronic pain, this is a crucial difference. One of his customers, for example, buys six chocolate bars every two weeks. “He says some days he eats a whole bar,” Weedman said. “Some people suffer from a lot of pain.”

Not all of Weedman’s customers are medicinal users though. Younger people buy more for the fun of getting high, while “the older ones—it’s their beer at night.” Many of his clients are “nine-to-fivers” and “office people stuck in cubicles.” Like him, they often turn to weed to unwind after a long day at work. “I like pot because it helps me relax,” he said as we drove south on Western to his next delivery. “Just the stupid stress that the city puts on you—it helps a lot with that.”

Weedman was born and raised in South America (but didn’t want to reveal which country). He grew up as a “latchkey kid” with a strict mom. Where he’s from, weed wasn’t seen as a harmless indulgence but as a hardcore drug, on par with cocaine, heroin, and the rest of it. “Pot was a big no-no for me.”

Still, teenage Weedman did try smoking once. He and a friend bought some herb, which “was all super shwaggy and dry.” They were rolling a joint behind a bush in a public park when a man pulled a gun on them and told them they were breaking the law. (Turned out he was a neighborhood watch vigilante, not an actual cop.) Weedman and his friend ran away, then smoked the joint. “I was so nervous I didn’t even feel anything, but my friend got sick,” Weedman said. They went to a local clinic, where a doctor brought in a gaggle of medical residents and used the stoned friend “as an example of what happens to people on drugs.” Young Weedman was freaked out.

He didn’t get back to pot until he came to America after high school to live with family in the southwest. He went to a community college where he first met “real” stoners who showed him that smoking weed was as much a culture as it was a fun way to temporarily mess with brain chemistry. Weedman dug the culture. “That’s when I started learning about Cypress Hill,” he recalled. “I was into Rage Against the Machine too. And I realized that it was on the left side of things, smoking pot.” Since the cops and other representatives of power and authority hate weed, he thought, there must be something inherently radical about it. “To this day I think it’s like a revolutionary thing to do.”

In the late 1990s, Weedman came to Chicago. For a while, he was a ramp worker for a major airline and also tried to start his own business. One day he met a man who ran a weed delivery service in New York City. Weedman figured he’d try supplementing his income by creating something similar in Chicago.

Procuring the wholesale supply at the time turned out to be a nightmare. “It was way out in the burbs and it was such an ordeal to get this weed and it ended up being super shitty weed,” he recalled. “I bought my first ounce of weed and it must have taken me a whole month to get rid of it,” he said. “I didn’t know that many people.” The stress of juggling three jobs was getting to him; his legal business faltered and he was eventually fired from the airport. “I was trying to hug too many things at once,” he said. “You can only hug one person at a time properly.”

Weedman got deeper into the weed business. He heard stories about the wonderful world of cannabis cultivation in Colorado and slowly connected with high-quality suppliers there. At first he rolled all the joints, packaged the flower, baked brownies, and made all the deliveries himself. He started out making a couple hundred dollars a week (“That was awesome”), then $500, then $1,000. Eventually he realized he couldn’t handle it all on his own and brought in some trustworthy friends to help. Weedman’s modest empire has grown to nearly 300 customers, most of whom are friends of friends of friends of friends. In a good year he now easily makes six figures. He said he’s poured much of his proceeds into retirement savings and health insurance costs, and also to help capitalize his legitimate gig, which now employs half a dozen people.

Weedman spends a typical day grinding at his day job, managing the mundane affairs of a small business. Most weed deliveries happen after hours, though some customers who work in restaurants like to buy in the mornings. He collects orders by noon so he can plan a route that’ll land him closer to home by the end of the night, usually around 11 PM.

The night I tagged along was unusually slow, just five scheduled drops. To kill some time, we stopped at Weedman’s legit business. Three of his employees were drinking beer and chatting with customers who seemed at home and lingered long after they finished what they came there to do. One of the guys who works in this business is also one of Weedman’s partners in the delivery business. He’s got a round face, short beard, and easy laugh. His client base is still small, only about 20 people, because he got “spooked.” Not long ago he was doing lunchtime weed delivery to office buildings, alongside delivering food through an app. A security guard in a Loop skyscraper searched him and found the weed and threatened to call the cops if he didn’t hand it over. Weedman Jr. lost an ounce of herb on that day.

The three of us talked in the back of the establishment. (Weedman’s casual about discussing the “dog walking” business here; his other employees know about it.) He’s proud of how he’s distinguished himself in the delivery game, even through small touches like the design of his inventory. The gummies, which contain 10 mg of THC each and come in packets of ten, are shaped like tiny monkeys, penguins, and lions. He opts for stiff brown paper pouches to sell the flower, with brightly colored stickers indicating the name of the strain. And he’s generous when he stuffs them, often putting in a bit more than the 3.5 grams equivalent to an eighth of an ounce. “My bags are fat,” Weedman said.

I asked how they make the pre-rolled joints, which are perfect cones packed tightly from filter to tip and twisted shut on the ends. Weedman pulled up a YouTube video on a dusty computer monitor. It showed a man’s meaty hands loading dozens of empty Raw brand rolling paper cones into a beehive-like machine. The man’s voice was matter-of-fact, and gallon-sized freezer bags of bud littered his work surface. “This guy’s doing a shitty job,” Weedman said as we watched the man using a coffee grinder to pulverize the delicate herb into dust. Weedman uses a hand-cranked grinder the size of a five-gallon bucket, which breaks the dry bud into more delicate chunks. “I’ve smoked pre-rolls all over this country, and I’ve paid top dollar for them,” Weedman said. “But to me, mine are the best. Mine are all flower.”

Weedman tries to stock only organic strains grown in the sun or in controlled indoor environments. (He spoke at length about the virtues of outdoor-grown versus greenhouse-grown versus indoor-grown pot.) His dry flower is carefully selected for potency and flavor and is “at most four months old from when you harvest it.” Weedman’s best-selling strains are indicas (which tend to relax and bring on drowsiness and the munchies) and “hybrids,” which are crosses between indicas and sativas (which tend to deliver a more heady, euphoric high).

Weedman predicts that legalization will make weed like craft beer. “I think there’ll be guys famous for the joints they roll—you want a joint shaped like a turkey for the holidays? There you go.” But he’s confident that the quality of his products will outshine what’s sold at the dispensaries. Plus, some customers will surely keep buying from him for political and philosophical reasons, as well as cost and convenience considerations. Many pot smokers who have long been into weed culture have no interest in supporting a state that criminalized them and their friends for decades and now aims to shore up its budget with tax revenue generated in businesses owned by rich white men.

Ultimately, Weedman wants to cut down his supply chain even more by growing his own strains “to have my own brand.” As he’s been dabbling in cultivation he’s learning that it’s “not rocket science” as long as you’ve got good seeds and the right conditions. “If you make the conditions of prehistoric times then your bud is gonna be strong and powerful.” It takes “a lot of CO2. When these plants were evolving that’s what the environment was like.” He seemed to notice me making mental calculations about what was going on in prehistoric times. “Dinosaur weed,” he said, his lips dissolving into a grin.

“I enjoy doing it,” Weedman said of his work as the car rolled east toward Ukrainian Village and the last of the night’s deliveries. “Ninety-nine percent of the people I’ve met doing this are just awesome people. Family people. They just love to smoke pot.” Most of his customers are white, perhaps because he lives mostly among white people. Weedman’s fine with it, though. “White people are chill, they’re never trying to find a deal,” he said. In his experience, people of color and immigrants like him love to haggle. (Weedman is the kind of guy who manages not to sound harsh even when he’s saying something judgmental.) “White people don’t haggle. I’m open to haggling but as long as it’s something reasonable—I can give you a better deal if you buy more.” He has a lot of south Asian customers. “Doctors. They like to haggle and they have money too. They’re rolling up in BMWs and Mercedes.”

Younger customers and first-time buyers can be shifty and nervous and in a rush. They don’t appreciate the romance of the weed deal, Weedman said. “Young people I don’t always groove with . . . But they usually don’t stick with me anyway because I’m not on their schedule. They want the Uber.” The on-demand commodification of almost every service has taken personal rapport out of drug dealing as much as any other business. But Weedman is old school. He doesn’t accept tips. He likes to “slow the roll” when he’s with customers, to ask them about stuff he sees in their home or how their day has been, to talk about Bernie Sanders, or breakups, or the Beatles for a spell.

Weedman treats each delivery like a visit with an acquaintance and not just a transaction, even though sometimes stepping into someone’s home can be unpleasant, especially if people hoard or don’t clean. “I’ve met a lot of gross people,” he said.

Sometimes, a relationship with a client fosters a deeper connection, even friendship. The next delivery is to a longtime customer who didn’t mind me accompanying Weedman into her home. A blond woman in her 30s with a bubbly voice, she welcomed us into her cozy living room wearing slippers and loungewear. Weedman opened his bag on the couch and pulled out a heavy-duty ziplock pouch full of herb packets. She described herself as a “really seasoned pot smoker,” and was relieved to find Weedman after moving here from Los Angeles where she’d been used to “really bougie” weed culture. She decides what strain to consume depending on her mood or the tasks at hand. “I do like a sativa when I need to clean my house,” she said. “A sativa edible and my house will be sparkling clean!” Weedman laughed and noted that people rarely buy sativa, which makes many paranoid. “I have a five-star review for this guy,” she said as we prepared to leave. “He always comes through for me.”

“My thing has always been just show up with some weed, that’s the reason I’ve been successful,” Weedman said. “I always come. The moment you don’t, someone else will.”

The last customer of the evening was running late, and Weedman parked his car in front of the man’s building in Ravenswood to wait. He used the lull to spark up a joint, one of his own pre-rolls kept in a long plastic canister in the center console. His tinted windows were shut and as he puffed, the vehicle fogged up with fragrant smoke. “It’s romantic,” he said, referring to joints, his favorite way to consume herb. “It’s nice to sit and grind the weed and smell it and have your own joint. It’s an event, it’s not just smoking weed out of a bowl. But hey,” he added, chuckling, “as long as you’re smoking weed it’s all good.”

We talked about music. Weedman loves punk and salsa—some of which is quite punk, he argued, and put on a Henry Fiol track to demonstrate. We talked about relationships, his decision not to have children, the difficulties of immigration. He still wants to go back to his home country one day, but, as the years go by, he finds it harder and harder to be comfortable there. The longer you live somewhere else, the more the place you’re from changes beyond recognition, “and you become a gringo too.”

This work has kept him grounded, though. His relationship with customers is based on a shared secret and on trust. Every transaction is an act of faith: he puts himself at risk being a dealer, but so do they, in welcoming a dealer into their homes. “You get to know people, you become friends with their pets,” he said, smiling through the cloud of smoke. He learns their tastes, the kind of art and music they enjoy, the ups and downs of their lives. Weedman’s sort of like a therapist. But even though he’s performing emotional labor, in the original sense of the term, it doesn’t weigh too heavily on him. “It’s mostly them telling me about their life and me, I’ll say stuff about myself that applies to what they’re talking about. I like to hype people up. If you’re having a shitty day and I can see it in your face, I’ll just tell you something to get you better.” Weedman’s happy to be part of customers’ self-care routine, to be a person they look forward to seeing and who connects them with something that brings joy and relaxation to their lives.

When the customer he’d been waiting for came home, Weedman went up to his apartment for the sale. He came back five minutes later. “Easy peasy,” he said. “There’s a cool kitty in there. This guy lets the cat pick his weed.”

The haze of the hotboxed car began to dissipate, and Weedman prepared to head home, looking forward to a hot dinner with his girlfriend and probably another joint. He told me he’d enjoyed talking about what he does. “It’s cool to get to say something,” he said. “I’ve never spoken about it.” I asked if there’s something he wanted people to know about weed, about people like him. He stared over the steering wheel for a few seconds. “Weed’s awesome,” he said finally. “Weed makes friends. Sometimes it makes things better. It makes you hungry, makes food taste better. It’s a lovely, lovely herb that someone put on the planet and you smoke it.” He paused again, weighing whether there was anything to add, or perhaps considering who that someone might have been. “Don’t hate on weed,” he said, “it’s been here longer than you have.”   v