The Sexiest Man in Winnipeg

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.

You can listen to The Sexiest Man in Winnipeg online on Radio and Podcast. Open the player on this page to stream the available audio.

The Sexiest Man in Winnipeg is an episode from Canadian Politics is Boring by Jesse Harley, Rhys Waters / Frequency Podcast Network.

This episode is 42:43 long.

This episode was published on Mar 30, 2026.

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