There was a time back in the 1990s when Steve Vogelsang was known as the “sexiest man in Winnipeg.”
A former sportscaster, college instructor and executive with True North Sports and Entertainment, Vogelsang helped several Winnipeggers shape their careers.
So when the Saskatoon native was arrested in 2017 for sticking up banks in Saskatchewan and Alberta, his once made-for-TV persona became rife with static.
“It raises a lot of questions,” said Charlie Siskel, a director and producer for “The Sexiest Man in Winnipeg,” a new documentary detailing Vogelsang’s rise and fall that releases Friday on Amazon’s Prime Video.
“What happened to this guy? Why did he end up robbing a bunch of banks? Why did he do it in such theatrically ridiculous fashion?”
Vogelsang was sentenced in 2019 to six and a half years in prison after pleading guilty to a string of bank robberies in Saskatchewan and Alberta between July and October 2017.
In one case, he walked into a Regina bank with a fake bomb strapped to his chest, slid a note to the teller demanding $50,000 and pleaded for help, saying “They’ve got my grandson.”
On its face, it’s a ridiculous but tragic story, says co-director Ben Daughtrey.
“We decided to embrace both sides of Steve’s personality,” he said in an interview.
“He is genuinely a funny person, but there’s also something ultimately tragic about a person going to these depths to try to change his life.”
In an interview from Washington state, Siskel said the documentary has been in the works since Vogelsang’s release from prison. Vogelsang himself was involved in its making, re-enacting elements and sharing his thoughts for the cameras.
The documentary also hears from several current and former Winnipeg reporters who knew Vogelsang and recall their shock at learning he had been arrested.
“The film is a character study, ultimately,” he said. “Not so much a whodunit because we know who committed the crimes, but a whydunit.”
Vogelsang’s trial heard the former broadcaster’s marriage had fallen apart, his prescribed medication for depression wasn’t working and he was deep in debt from lengthy unemployment.
Asked why Vogelsang gets a documentary when ordinary people convicted of bank robberies don’t, Siskel said humans are obsessed with true crime and fame. His crimes were minor, so it’s all the more surprising, the director said, that Vogelsang thought it was his way back.
“What is it about these crimes and criminals and crime stories that so fascinates the public and makes such a ready market for these kinds of stories ... Is this all fame seeking on his part? ... What role do we have in turning these people back into celebrities?”
Siskel said the viewer should “play jury” when watching the documentary. Was Vogelsang “some sort of monster,” he said, or an ordinary person who got a taste of fame, lost it and went about a “weird way” of getting it back?
Siskel adds that Vogelsang routinely points out in the film that he doesn’t want “that much fame.”
But Siskel thinks otherwise.
“I do think that fame and fame seeking is at the heart of Steve’s story,” he said. “I think there is an element of redemption in the sense that Steve is coming to terms with his own past and his choices.
“Is it a redemption story, is it exposing the deep flaws of another human being, or is it something in between?”
This report by The Canadian Press was first published May 9, 2025.
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