A Winnipeg senior who spent four decades behind bars is now looking at the possibility of life in prison.

Gerald Joseph Pilon — or Joey as he's known to his friends — hasn't killed anyone, but he's done hard time at just about every maximum security federal penitentiary in Canada. Now 60, Pilon has spent more years locked up than some of this country's convicted killers, for crimes in which he didn't physically harm anyone.

But make no mistake, Pilon is no angel. On paper, he has an extensive criminal record and has been convicted 51 times for theft, breaking and entering and armed robbery.

"It's been a long ride for me," said Pilon in an interview with CBC at Milner Ridge Correctional Centre, where he's awaiting trial for two counts of armed robbery.

"You learn to live what you know. I learned a few things. I only quit stealing. Every time I did go back to prison."

Pilon hasn't lived outside a correctional facility for more than a few months at a time since he was 15. After serving sentence after sentence, the lifelong offender would eventually wind up right back behind bars.

Gerald Joseph Pilon, 60, is facing life in prison for two armed robberies. (Tyson Koschik/CBC)

After serving a total of 41 years and 25 days in custody for various crimes, Pilon was released in December 2014. Somehow, he survived for two whole years on his own.

That's an incredible accomplishment, criminologist and Okanagan College Prof. Melissa Munn said.

"Nobody predicted he would last two years on the street. Certainly the people within the system did not," Munn said in a phone interview from Vernon, B.C.

"So the fact that he did this well with the limited amount of support he'd been given post-release is testament to the fact he really wanted it. He really wanted to be able to go straight, to succeed afterward. He was tired of doing time."

Difficult childhood

Pilon grew up in Badger, Man., with his aunts and uncles. At the age of six, he and his five siblings moved to Winnipeg to live with their parents. But it didn't last very long. Pilon's mother and father struggled with alcohol addictions, so the children were apprehended by Child and Family Services and sent to live in different foster homes.

Pilon ran away from every foster family and group home he was placed in.

"I took my brother, my two younger brothers. We went back to the place we used to live, which was [on] Andrews and Dufferin in [Winnipeg's] North End," said Pilon.

When they got there, the place had been torn apart and the kids' parents were nowhere to be found.

"I found all the photographs in the backyard and I was wondering, 'Where are they?' So I kept running away, is what I basically did, from wherever they put me."

Pilon remembers stealing from an early age. At first, it was mostly food and candy, which he shared with his siblings. He was placed in a girls' and boys' home, then later a juvenile detention centre, but it didn't do much to curb his bad behaviour.

Pilon said no matter how hard anyone tried to convince him to stay in one place, he kept running.

"Always running away, looking for my parents kind of thing. I met them on the street a few times here and there but never to go to their place or whatnot. They were on welfare, moved all the time."

Sent to adult prison at 16

By the age of 16, Pilon had been convicted of 100 crimes. He had been in trouble with the law since he was eight years old and had no plans to straighten up.

On June 12, 1973, 10 days after his 16th birthday, Pilon pleaded guilty to three more charges after he and six other youths escaped from a juvenile detention centre and attempted to break into a number of homes in Winnipeg's West End. Pilon's 1973 conviction was featured in the Winnipeg Free Press at the time. (Winnipeg Free Press Archive)

At the sentencing hearing, the judge said the teen showed no interest in rehabilitation and that attempts to help him were "an exercise in frustration," said a Winnipeg Free Press article written at the time.

It was the last straw for Pilon, who received an adult sentence of two years to be served at a federal prison — Stony Mountain Institution.

He knew his father was serving time there for theft and that's where they reconnected.

"It was the only time I got to see him, basically, so it was good," said Pilon, who served just under a year alongside his father, whom he desperately wanted to know.

'This man has done enough time'

Munn works with long-term offenders to prepare them for life outside prison walls. She met Pilon five years ago after a fellow inmate she had been helping suggested she look into his case.

"This man has done enough time.… It's not acting as a deterrent. It's not meeting any of the goals of sentencing except to be punitive. It's the only reason that we're going to send this man to prison again, is to be punitive," said Munn.

"His is a heartbreaking story. Joey is … you know, on paper he is a chronic offender. On paper he is the cautionary tale but in reality, when you speak to him and when you get at the conditions under which he committed these crimes and he has done hard time, it points to a systematic failure," Munn said.

"It points to a systematic failure and one that we have to accept some responsibility for."

Gerald Joseph Pilon learned tattooing at the age of 15 from another inmate at Stony Mountain Institution. (Tyson Koschik/CBC) Munn said Pilon came up through the system under the Juvenile Delinquent Act and the justice system has evolved since then.

"I think to send a child to a men's penitentiary is, at this stage, incomprehensible. We would never do that. We have enough understanding of the impact of that kind of action to know not to do it. And I think the fact that we did that, and for what was relatively a minor crime, is really our shame, and Joey is the product of a system that failed him," said Munn.

Facing life in prison

Pilon doesn't blame anybody for his actions and takes full responsibility for the choices he made. Later this month, he plans to plead guilty to two counts of armed robbery.

Looking back on what he calls a "pretty bad life," the now 60-year-old wishes he had done things differently.

"I stayed away from most people. I did what I wanted to do. But I look back today and I think maybe I should have listened to this person, listened to that person," Pilon said.

"I wish I would have grown up sooner."

Munn believes it's unlikely Pilon can avoid additional prison time, but hopes the courts show compassion and don't sentence him to life.

Criminologist and Okanagan College professor Melissa Munn believes Pilon is a product of a youth justice system that failed him. (CBC) "I think the struggle became too much and so it's not surprising to me when you feel overwhelmed by decision making, by all the challenges that would have confronted him on a daily basis that he would have gone back to what he knew. Found a way, subconsciously or unconsciously, to go back to the familiarity of prison where he doesn't have all those decisions to make," said Munn.

If given another chance at freedom, Pilon plans to focus on his tattoos. His body is nearly covered in art, a skill he first learned at age 15 in Stony Mountain.

"I don't have much of a future left, to tell you the truth, but whatever there is left of it I want to make the best of it when I'm done with this," said Pilon.