Puffing a joint on his deathbed, Rosie Rowbotham is feeling fine. His shirt’s off, Muffin the cat is by his side, and he’s talking about the happiest days of his life. “Rochdale,” he says, and he smiles, all skin and bones, bottom teeth missing, a wisp of smoke now enveloping his tousled, long white hair. Rochdale, a now-defunct experimental college along Bloor Street in Toronto, is where Mr. Rowbotham set up shop in the late 1960s to become not just the biggest hash dealer in the country, but one of the most successful cannabis salesmen in the world.

“If you bought hash in the seventies, I don’t care if you were in California, Boston or Chicago, you got it from me,” says the man born Robert Wilson Rowbotham in Belleville, Ont., on Oct. 31, 1950, and who, in 1985, would begin serving the longest sentence for trafficking weed of any Canadian in history.

At his 1974 trial, Norman Mailer testified on his behalf, and when Mr. Rowbotham stood up in court and told the judge he’d continue dealing pot because there was nothing wrong with a hippie selling flowers, he’d eaten a quarter ounce of hash that morning in a Brampton jail.

“I felt good turning everybody on to a spiritual thing with the smoke. I wasn’t a criminal. I was a pothead, I was a hash man,” he says.

But the police took his grandstanding seriously, and after he was released in 1982, the Drug Squad tapped his phone and he was busted again, this time in 1985 with about 7,000 kilograms of Lebanese hash. Mr. Rowbotham told the cops he’d keep dealing weed and he did. He says, “I was General Patton in the War on Drugs.”

The war has taken its toll on Mr. Rowbotham and, after serving his 20 years, many of them at the Millhaven Institution in Kingston – a maximum-security prison for violent offenders – he was diagnosed with prostate cancer, which is currently stage four. He’s uncertain he’ll see his 72nd birthday.

At his tidy house off Bathurst Street where cannabis plants grow nine-feet-tall in the backyard, Mr. Rowbotham, who is awaiting a third round of radiation treatment, smokes now not for euphoria, but to feel momentarily transported from physical and spiritual pain.

“One thing about dying is you come to make a certain peace with yourself,” says Mr. Rowbotham, who has never inhaled a breath of legal Canadian weed. “I knew legalization was coming, but it doesn’t feel earned by the people in the business today. I gave up everything for the cause, for the movement – my freedom, my family – and what did it get me? I don’t even have enough money to pay for my grave.”

Legalization of cannabis was officially enacted in Canada on Oct. 17, 2018, and the country is on the eve of the fourth anniversary of becoming the first G7 country to legalize weed. Mr. Rowbotham, however, like many early activists and dealers (and sometimes it’s hard telling the two groups apart), says he feels disdain for the business he once ruled.

“The legal-cannabis industry in this country is going to collapse on itself because the karma is wrong – it’s all greed,” he says. “The industry cheats and thieves and hides pot in the walls. It’s dirty. I broke the law, but my karma is clean.”

Mr. Rowbotham says he had a Rockwellian home life growing up and that his parents, Alfred and Grace, a veteran and a homemaker respectively, were generous and attentive with their four kids.

Mr. Rowbotham has two older brothers and a younger sister and remembers his parents as happily married. His dad bought land on the same street as his grandfather and uncle for a buck on the GI Bill, and built a house there.

“I wasn’t running away from something, I was running to something,” he says, and found what he was looking for the first time he got high. “I was 15 at a local girl’s place, she was babysitting and her parents were out and she had ganja and we started smoking. It felt so hip.”

Mr. Rowbotham immersed himself in the nascent culture, digging Led Zeppelin and LSD, and began making trips to 1966 Yorkville, a counterculture neighbourhood in Toronto, to score cannabis which he would bring 200 kilometres back to Belleville and smoke with the girls. “I wanted to be a hippie. I had no intention of being anything else.”

He was busted at age 17 with an ounce of hash and served 30 days. “Reefer was so vilified that I wasn’t even old enough to serve, but here I am, a brown-shirt youth offender digging holes at Burritts Rapids jail – might as well have been selling fentanyl in today’s relative terms,” he says of the bust that had the inverse effect of straightening him out. Instead, he dropped out of tenth grade and moved to Yorkville, where he busked, washed floors and delivered the Toronto Star, until dealing hash and weed.

The vocation, he says, came naturally. “The small-town kids that came to Toronto ended up being the hustlers because we were hungry,” he says, then mentions the fortuitous moment that changed his life – a friend from Belleville had gotten a job as the renovation manager at Rochdale, and offered Mr. Rowbotham room 617 for $60 per month. “Males and females using the same showers – I walked into the perfect place for me,” he says. “If I was a pariah back in Belleville, now university kids were buying pounds of pot off me.”

Mr. Rowbotham says Rochdale was the ideal place to deal cannabis because security kept the drug dealers out, and left the pot dealing to him.

“My motto was: no speed freaks, no rip-offs, no guns and no bikers,” he says. “Everyone felt safe, and on a Friday night in 1969 I could do between $5 and $10,000. I’d have 60, 70 people lined up out my door and had to hustle real fast or the retailers would get together and buy wholesale, which was my bag.” Mr. Rowbotham cycled all of his earnings into buying more product.

“The story of my existence is spinning – a hundred grand here, fifty thousand there, let’s go.”

Moving as much as ten kilos per week, Mr. Rowbotham thought he was king of the world because he could splurge at Harvey’s, but his life as a hash man was about to explode. In front of Sam the Record Man, smoking a cigarette in the summer of 1970, Mr. Rowbotham was approached by two Lebanese businessmen. “Are you Rosie Rowbotham, the guy who sells hash at Rochdale?” one man asked him, and the 20-year-old demurred.

“If you’re looking for a confession, you got the wrong guy,” replied Mr. Rowbotham but, after a short conversation, the young dealer’s interest was piqued. The men made the kid an offer: In the trunk of a car parked beside Varsity Stadium at University of Toronto, there was a ton of hash. The keys were in the car’s ashtray. “Don’t worry about getting a hold of us,” the men told Mr. Rowbotham. “We’ll get a hold of you.”

Mr. Rowbotham remembers picking up the car with no licence and unloading 16 crates of hash into the freight elevator at Rochdale. He describes the eeriness of dragging the black tar down the hall. “It was the afternoon, 3 p.m., quiet, quiet, quiet – everyone still asleep,” says Mr. Rowbotham, who still marvels at how his life changed. “A year ago, I had bought 10-cent macaroni-and-cheese dinners to live on and panhandled 15 cents for the subway and now I had a ton of hash, and these new partners. I was also on the hook for a million bucks.”

Setting up six stash rooms at Rochdale, Mr. Rowbotham charged $590 per kilogram and maintained a reputation for quality, chill and fairness. “The people who used to sell to me were now buying 50 pounds of hash and I started supplying Montreal, Ottawa; plus, the Americans were coming up from Ann Arbor and buying dope left, right and centre. I had people from California buying 500 pounds.”

The initial load was gone in a month and Mr. Rowbotham expanded into mescaline and acid, but drew the line at cocaine. “When people started freebasing, I knew it wasn’t for me – bad karma,” he says, and maintains that he adhered to a strict moral code: Cannabis was not meant to be constricted by laws. “What I was doing was righteous,” he says. “Even my battles with cops.”

An important part of Mr. Rowbotham’s Rochdale existence was fighting the authorities, sometimes in the streets.

“We were always having riots – you can’t imagine the disdain we had for the pigs,” he says, “but the word ‘busted’ wasn’t part of my vocabulary because the pigs couldn’t get into Rochdale, though every once in a while they’d kick down the doors.”

Once, in the early 1970s, Mr. Rowbotham says he and his friends commandeered a TTC bus along Bloor Street after the police manhandled a pregnant woman and used rubber bullets on the hippies to disperse the crowd. “A hundred cops came and we’d play Sympathy for the Devil and I remember the Friday night in Toronto, the first cruiser got there and we smashed a brick through his window and this was cannabis – it was a way of life.”

Mr. Rowbotham had thousands of kilos of hash in six stash rooms above the riot, but physically confronted the police.

“The cannabis movement meant something to me. And if you fought for a cause,” he says, “you fought until the end.”

Mr. Rowbotham was arrested in 1974, then 1982, and then 1985, in a sting called Operation Rosie. By then, after a long spread written in 1977 by Barbara Amiel in Maclean’s, his activism had become renowned and he could count among his celebrity friends Alice Cooper and Neil Young.

Norman Mailer was fond of Mr. Rowbotham, who told the American author that he didn’t read books. “Some people read, some people write – and some people have books written about them,” Mr. Rowbotham said, and shared a pound of marijuana with the author who would later appear as a character witness at his trial.

Alan Young defended Mr. Rowbotham in 1984 and again at his appeal in 1989, and the two men shared a love of cannabis and cannabis culture. Mr. Young, who would go on to work with Health Canada on drafting the laws that would help legalize cannabis, which began in 2001 with the Marijuana Medical Access Regulations (MMAR), says the severity of Mr. Rowbotham’s sentence for cannabis trafficking made him reappraise Canadian justice.

“This was my client, my friend, who was being sentenced to more time than serious violent criminals for selling pot and the whole legal system was revealing itself as a farce,” says Mr. Young, whose experiences with Mr. Rowbotham would forge his legal career, trying cases for drug literature (1993), medical cannabis exemptions (1999) and compassion clubs (2000-2016), which set the template for the cannabis dispensaries we have today.

Says Mr. Young, “Rosie was a catalyst for all of this change.”

The MMAR laws were the first radical change in Canadian cannabis regulation. They allowed for medical consumption of cannabis produced legally by either designated growers – people legally entitled to grow cannabis for patients with a medical licence – or else Prairie Plant Systems, the first Canadian licensed producer, which was based in Flin Flon, Man., and grew their pot in an underground Hudson Bay mine.

From a halfway house into which he was released in 1998 and then during the ensuing years that he spent on parole, Mr. Rowbotham watched the cannabis culture morph into a regulated industry. “Eventually I was a casualty, but I never sold out and it was an honour as a warrior to serve 20 years,” Mr. Rowbotham says.

While Mr. Rowbotham found work at the CBC as a contributing editor, the country would extend its licensed producer system in 2013, ending the Prairie Plant Systems monopoly and allowing multiple companies to produce legal Canadian medical marijuana. This led to the rise of licensed producers such as Aurora and Canopy Growth, none of which could legally grant security clearance to a felon with a cannabis conviction, and none of which made inroads to Mr. Rowbotham. “Who are these people who come and sell pot and say, ‘Oh, I’m doing it for the government.’ Who are you? What have you done?” says Mr. Rowbotham, who, like Mr. Young, says that he always knew full recreational legalization was coming and that Justin Trudeau’s legalization campaign promise in 2015 was a fait accompli.

“The government got rid of me so it could set up its own pot companies, but karma is everything, and if you create an industry built on greed, there’s nothing it can do but collapse.”

Mr. Rowbotham knows it’s too late for him to get into legal weed and he feels conflicted – sometimes resigned, sometimes raging – but he still believes a hippie should be able to sell flowers. He blames the chemo for altering his lucidity, but the cannabis seems to replace the anger with nostalgia and something like grace. “Everything that’s happened to me sometimes feels like it was written,” he says, and dreams of passing onto the legal industry the lessons he learned in his youth, even as time is running out for him.

Since cannabis legalization, Canopy Growth had a peak valuation of more than $20-billion, but it lost $2.1-billion in the first quarter of its 2023 fiscal year. Mr. Rowbotham insinuates that he never went in the red because the Lebanese businessmen knew where he lived. Perhaps there could have been more accountability in the legal industry with real stakes around the bottom line. Meanwhile, over 425 tonnes of unsold cannabis were destroyed last year in this country. On his own, Mr. Rowbotham says, he could flip a ton of hash in three weeks – let alone mescaline and LSD. Selling pot, he continues, comes down not only to supply and demand, but also, he says, trust between buyer and seller.

“You got what I told you you’d get, the weight was there and the quality was there,” he says, describing his dealings in contrast to that of the government. “There was no fear of being ripped off and you could sit down, smoke a joint and relax.”

As we approach the fourth anniversary of cannabis legalization, the industry has generated more than $43-billion to the country’s economy, according to a 2022 Deliotte Canada report. But Mr. Rowbotham is skeptical of the industry, saying he doesn’t understand why some white-collared Canadian cannabis executives avoid prison while dealers from the 1970s who served their sentence are seen as convicts and crooks. “The guy who was honest gets crucified, but these government guys, they’ll do anything. Call me a fool, but I don’t want to have my name associated with them.”

Earlier this month, U.S. President Joe Biden called for a federal review of the American cannabis laws and announced pardons for all federal offences for marijuana possession. He also encouraged state regulators to do the same thing. It’s a start, Rosie Rowbotham says. But he sees the future of Canadian pot businesses in an initiative started in Oakland.

“Look at California, they did it right – let the dealers run the thing,” says Mr. Rowbotham, mentioning Oakland’s progressive social-equity initiative, which gives priority to run cannabis businesses to residents who have had non-violent cannabis arrests. While the California initiative was meant to empower minorities who are disproportionately arrested for cannabis crimes, Mr. Rowbotham believes the Cannabis Act, which legalized cannabis and is currently being reviewed, should learn from the cannabis culture that the legal system supplanted.

“Selling marijuana doesn’t have to be about thievery and greed,” Mr. Rowbotham says with a knowing smile as he takes a last pull from his joint. “It’s too late to hire people like me in Canada. I’m stage four, I’m dying – but us kids in bell-bottoms knew something that these rich guys in government can’t figure out: It’s not always about money.”

Story from – The Globe and Mail