by Aaron Souse
The Canadain Press
Winnipeg’s Classic 107
May 9, 2025
A former sportscaster, college instructor and executive with True North Sports and Entertainment, Steve 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.
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