
The Sexiest Man in Winnipeg
From Canada is Boring by Jesse Harley, Rhys Waters
March 30, 2026 · 43 min · Episode 510
About this episode
The episode explores the bizarre life of Steve Vogelsang, from local celebrity to bank robber and mental health advocate.
In this episode of Canada Is Boring , Rhys and Jesse dive into the bizarre true story behind Amazon Prime’s The Sexiest Man in Winnipeg , following former Winnipeg TV news anchor Steve Vogelsang from 1990s local celebrity and “sexiest man” titleholder to financially ruined, depressed journalism instructor living in his truck and ultimately turning to a hilariously low‑yield bank robbery spree across Regina, Saskatoon, and Medicine Hat. They unpack his “plan” to rob 25 banks for a few thousand dollars at a time using fake bombs and a glue gun, the legal quirks of what counts as armed robbery in Canada, how he was eventually caught after his truck broke down near the scene, his 6.5‑year prison term, and his attempt to rebrand himself as a men’s mental health advocate For premium content, socials, merch, to leave a voicemail or message us go to canadaisboring.com Hosted on Acast. See acast.com/privacy for more information.
People in this episode
Hosts: Rhys Waters, Jesse Harley
Topics covered
- true crime
- mental health
- bank robbery
- Canadian culture
- local celebrity
Keywords
- Steve Vogelsang
- bank robbery
- Winnipeg
- mental health
- true crime
- Amazon Prime
Mentioned in this episode
Organizations: Amazon Prime
Places: Winnipeg, Regina, Saskatoon, Medicine Hat
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