Ever made a bet you thought you had no chance of losing, but somehow – even with all the odds stacked in your favour – the world worked against you and you managed to lost it anyways?

That’s probably how Toronto mayor John Tory is feeling right now. 

No one thought the Montreal Canadiens had any chance at all against the Maple Leafs, and no one predicted that they would sweep the Winnipeg Jets, but here we are. 

If you’re a Toronto fan, this one stings particularity badly. 

This season (like many others) was supposed to be theirs, and suddenly, the CN Tower is lit up in Canadiens colours. 

Life comes at ya fast, Leaf fans. 



Today, Toronto got even more Hab-ified when John Tory had to make good on a bet he made with Montreal’s mayor and fly a Canadiens flag at city hall. 



Dang, this loss truly just keeps getting worse for Leafs fans. 

Hey, there’s always next year! 

(H/T: JohnTory)