Former Headingley inmates in a new kind of fight: one for a sober, better life

Two ex-inmates at Headingley Correctional Centre are now on the outside and looking in, but not because they want to return to jail. They're just unsure of where to go next.

'I'm trying to correct all the harmful things that I've done,' says Jeremy Raven

'I wasn't living with any kind of boundaries' before jail, says former Headingley Correctional Centre inmate Jeremy Raven. (Jeff Stapleton/CBC)

They're two ex-inmates who are now on the outside and looking in.

But it's not because they want to return to jail. They're just unsure of where to go next.

"It's overwhelming," Jeremy Raven says softly. "I'm trying to correct all the harmful, destructive things that I've done, but there's all the pain and the hurt."

It is March 2020, and Raven is three months out of jail. He's seated next to Jason Walmsley, who is in his ninth month of freedom.

In the warm glow of a softly lit CBC Manitoba studio, it is a reunion of sorts.

Both were formerly incarcerated at Headingley Correctional Centre, just outside Winnipeg. Both spent their time behind bars as participants of the Winding River Therapeutic Community, undertaking intensive and unique addictions treatment. 

I drank. I drugged. I was selfish.- Jeremy Raven

It was then that CBC first met with Raven, Walmsley and two other participants on their turf — in the locked confines of a cinderblock jail room — to learn more about Winding River. 

At the time, the four inmates called it an emotional game-changer. It was the first time they'd gotten the help they needed to take on the demons of their past traumas — demons that, for most of their lives, were fuelled by the drugs they abused and the crimes they'd committed to buy those drugs.

It also meant that all of them, upon their release, would face life on the outside in a new, unfamiliar light — sober.

It's not easy.

Two of the four are again struggling, they say. One of them is back in jail, the other one lost to the streets.

In April 2019, the CBC's Marcy Markusa listened as Jeremy Raven, right, then an inmate at Headingley Correctional Centre, shared his story. (Donna Carreiro/CBC)

Raven says he is not the same man as the one before he entered jail.

"I drank. I drugged. I was selfish," he said.

But eschewing that former life meant changing everything about it, and his past is present everywhere.

"It could be just walking down the street or going to catch a bus," he said. "I run into friends and family members that are triggers for me."

Explaining himself to them, which sometimes means turning his back on them, is hard.

"I feel like a sense of guilt, almost, because we've been through so much," he said. "But in the same sense, I'm trying to live a better lifestyle than what I was doing, because the end result was that I ended up in jail."

Jason Walmsley can relate.

Friends from the past will tell him, "Hey, let's get high," he said — and he says no.

"When have I ever said 'sorry, I can't?'" Walmsley said. "You're telling them things you've never told them before."

Searching for support

Seeking out supports is tops on their daily agenda. And most often, it's up to them to find those supports, whether they be housing, counselling or schooling. Once they stepped foot out of jail, they were on their own.

Walmsley spent months in daily rehab, before transitioning into the community.

Raven still spends mornings in a treatment program and afternoons busing from one drop-in addictions meeting to another.

Jason Walmsley, left, and Jeremy Raven, centre, speak with Information Radio host Marcy Markusa in a CBC Manitoba studio. (Jeff Stapleton/CBC)

He also reads a lot (both he and Walmsley read the dictionary while in jail).

"Now, I'm reading The Power of Positive Thinking," Raven said.

Both of them admit they feel a bit lost. 

"Lots of anxiety," Raven said simply. "Anxious."

Sometimes, it's exhausting. 

"I'd just like for there to be one day when I'm not 'Jason in recovery,'" said Walmsley. "I just want to be Jason."

Every time he shows me love, I love it.- Jason Walmsley on his brother's support

But while the hard of recovery is bad, the good of recovery is great, they say.

The first time Raven was reunited with his almost four-year-old son was emotional, he says.

"It's a wonderful feeling," he said.

WATCH | Jeremy Raven on talking to his son for the first time after jail:

Jeremy Raven on the gift that comes with sobriety

2 years ago
Duration 0:53
Jeremy Raven describes the first time he communicated with his hearing-impaired son, since his release from jail.

An even better feeling? The first time he communicated with his son, who is hearing impaired.

"That's the best feeling in the world," said Raven, adding that he's teaching himself sign language.

"So it was just a simple 'hello' and him telling me to sit down, so he could crawl on my back and play."

His six-year-old daughter is now helping him learn more sign language.

"Just being able to spend time with them and run around with them is so good."

Reconnecting with Walmsley 'was good,' says Raven, 'because I heard he was still pursuing the life that he's chosen.' (Jeff Stapleton/CBC)

Walmsley has reconnected with his brother.

"Every time he shows me love, I love it," he says. "He called me 'bud' the other day, and it means a lot."

These are the payoff moments, they say — the moments that reinforce their journey into uncharted sober waters is the right course to take, despite the sometimes rough tide.

It's why Raven (who says he has only a Grade 6 education) is actively seeking out adult education. It's why Walmsley is making his way back into the work force. 

It's why both of them, now reconnected after their time in jail, plan to together attend the monthly Winding River meetings in the community.

"I'm just trying to lead a better life," said Raven. "My recovery must come first, so the people I love in life do not have to come last."

Sober and better life

2 years ago
Duration 4:37
Former Headingley inmates say the moments that reinforce their journey into uncharted sober waters is the right course to take, despite the sometimes rough tide.


Donna Carreiro

CBC Radio Current Affairs Producer

Donna Carreiro is an award-winning producer and journalist, who has worked for more than 27 years with CBC Manitoba. Prior to that, she was a print journalist for a daily newspaper and local magazines. She is drawn to stories of social justice (or injustice) that give a voice to those who most need one. She can be reached at