Put a Big Red Circle Around March 20th

Steven Colbert and Oshawa Mayor John Gray made a schoolyard bet not too long ago. The bet? Who was going to win a hockey match between the Oshawa Generals and Michigan's Saginaw Spirit in an Ontario Hockey League match. Colbert has been a huge fan of The Spirit since they named their mascot - Steagle Colbeagle the Eagle - after him. Mayor John Gray issued the challenge himself to Steven Colbert through a radio station.

The prize? If Oshawa won, then Colbert would have to wear a Generals jersey on his show. If The Spirit won, then Steven Colbert would get his own "Day" in Oshawa, the specific marker being on his birthday. Colbert decided the bet would be better if Steven Colbert Day was on the Mayor's birthday instead.

Can you guess who won? YouTube videos, after the jump.

The Colbert Report, January 27th, before the game

The Colbert Report, January 29th, after the game

No, it's not specifically Toronto related, but it's damn awesome nonetheless.


Latest Videos



Latest Videos


Join the conversation Load comments

Latest in Sports & Play

Runner turns Toronto map into a giant cartoon animation

Here's how to get tickets for the 2026 FIFA World Cup games in Toronto

William Nylander models for new Toronto Maple Leafs collab with OVO

Toronto's free outdoor skating rinks are about to open for the season

Toronto Raptor pulled over by police before attending party at nightclub

Andre 3000 just performed a set wearing a Toronto Maple Leafs jersey

Ex-Toronto Raptor OG Anunoby had hilarious encounter with Anne Hathaway

Toronto Blue Jays fans seem annoyed team is posting about Taylor Swift