Time served: What's life after jail really like? episode artwork

EPISODE · Mar 19, 2026 · 54 MIN

Time served: What's life after jail really like?

from Now or Never

Today an estimated 35,000 Canadians are behind bars in a provincial or federal prison. But what happens to people once they get out?Transitioning back into society can be challenging, with barriers around housing, employment, and the stigma of a criminal record. According to one study, around 70 per cent of inmates with addiction or mental health issues end up back in prison within three years.So what does it take to rebuild your life after incarceration? On this episode, meet former and current inmates doing the hard work of repairing relationships, finding a job, and staying sober.Yassir Kassam spent the last 30 years in and out of jail, drawing his family into his cycle of addiction and deception. Today, seven months out, Yassir sits down with his younger brother Omer for an honest conversation about the impacts of his actions on both of them, and what it takes to trust and move forward.When Darcy Beardy got released from prison last August, he had a hard time finding a job — until he met Sean Rayland-Boubar. Sean knows first-hand the challenges of turning your life around after prison, so he created Red Rebel Armour, an Indigenous streetwear company with the mission of giving a second chance to men just out of prison. Darcy and Sean talk mentorship, responsibility, and what it takes to "walk the good path."“I’ll either be doing life in prison, or I’ll be dead.” That’s what former foster kid and current gang member Devon Henderson told Now or Never producer Bridget Forbes this summer, after picking up a gun for the first time in his life. But when they first met five years ago, Devon’s future looked hopeful. So what happened? And is there any way Devon can see a third option? Bridget goes behind bars for a face-to-face conversation with Devon.

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Time served: What's life after jail really like?

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