At one point in the 1970s, if you were smoking a joint anywhere from Vancouver to rural Indiana, there was a good chance Robert “Rosie” Rowbotham was responsible. Rowbotham, whose nickname stems from childhood, was the preeminent hippie capitalist of his day, spreading peace, love and red eyes across the continent. He was one of the largest suppliers of marijuana and hashish in North America and he did it all with a smile plastered on his face.

It isn’t rude or sexual. It is a practical discussion about the carrying capacity of a particular body cavity and one I feel at once captivated and trapped by. I am here to chat with Rosie about his life and that is exactly what I am getting.

As we sit around a picnic table in his Toronto backyard, Rowbotham, is munching on a burger and bickering with his lifelong buddy, Billy, about the veracity of anal fisting. It began innocently enough with the two near-70-year-olds debating just how much hash you can stuff up your ass to smuggle into prison. But, when Rosie suggests an amount of hash so vast that Billy can only recoil in horror, Rosie is adamant that humans have amazingly flexible assholes. A discussion about anal fisting between the grandpas ensues.

Now 67 and retired, Rowbotham, once described as the “Mr. Big” of the soft drug trade in North America, is an anti-establishment senior citizen on the outside looking in. His convictions make it impossible for him to participate in the economy he kick-started 50 years ago.

Rowbotham was back in the news as Canada legalized weed last October, this time as an outspoken critic not only of the country’s approach to legalization, but of those who are implementing and profiting from it.

And for his service, he went through four criminal trials, was given Canada’s longest ever sentence for cannabis in 1985 and, spent more than 20 years in prison for conspiracy to import, distribute and sell cannabis.

Without hesitation, Rowbotham says, “No, not at all.” Billy, looks at me, and says, “Yes, you do.” I believe them both. Billy’s answer reflects the rule. Rowbotham’s answer is the exception. Rowbotham, charming and unflappable with a gift for selective introspection, has been the exception that proves the rule most of his life.

The shock registers on my face, I know it. I ask if it in that moment, when you accept you are using your ass as a suitcase, do you ask yourself, how the hell did I get here?

He was an unbridled success and expanded his business interests to include a vegetarian restaurant, a music promotions business called Fillmore North and developed what today we would call a “lifestyle brand” with his Sweetwater boutique. By his mid-20s, Rowbotham estimates he was clearing close to a quarter of a million dollars a year, but he never flaunted his wealth.

Without a high school diploma and already possessing a criminal record, he wasn’t rife with job prospects upon arriving in Toronto. Rosie did what guidance counsellors the world over encourage young people to do: he turned what he loved into his job.

What began with selling grams from his dorm room morphed into renting six apartments at a time to stash the one thousand pounds of product he was wholesaling per week.

“The cops had dragged me right outta class to jail, I did my 30 days then they sent me right back to class and I hated it. I borrowed ten bucks from my mother and took off for Rochdale,” he told me.

In the summer of 1968, Rowbotham was 17 and had just completed 30 days in the Belleville, Ontario jail for pot trafficking. He couldn’t get out of town fast enough.

Rowbotham, though certainly enamoured with all his lifestyle afforded him—he partied with everyone from Alice Cooper to Norman Mailer and loved fine dining—was conscientious of the challenges facing his hippie brethren. He funneled his drug profits back into his other businesses and offered employment to an endless stream of young people deemed “unhirable” by the straight workforce.

But more than just profiting off weed and serving as a Robin Hood figure for the hippie community, Rowbotham endorsed and defended the use of cannabis. Charismatic and committed, he was unrepentant as he challenged the courts to address their backwards attitude towards weed.

In the spring of 1977, Rowbotham stood trial, charged with conspiracy to import and distribute one ton of hashish in 1974. Rowbotham was convicted and sentenced to 14 years, which was reduced to nine years through appeals.

Rowbotham believes there were a couple of contributing factors for the stiff sentence. “I did this big spread in Maclean’s that drew a lot of attention, and then, secondly, I got up in court and did my little ditty with the judge,” he explains.

The “little ditty” Rowbotham is referring to is the hour-long impassioned speech he gave to the court regarding his belief that putting him, a peace-loving hippie, into a den of violence for selling a drug that does no harm was wrong. He went on to proclaim that if he were put in prison, he would continue selling cannabis upon his release.

“I was unrepentant and they didn’t like that. It also didn’t help that I ate a quarter ounce of hash that morning in the Brampton jail before addressing the judge. It likely contributed to the length of my statement and my sentence but I believed it and still do,” he said.