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Come Fan with UsThursday, July 2, 2026

Youppi! lost the saddest bet of all time over Habs-Rangers

Youppi! had to take pictures in a Rangers jersey. He chose to make them sad carousel pictures.

The life of Youppi! is a sad one. He used to be the mascot of the Expos, but since the Expos no longer exist, he’s now the mascot of the Montreal Canadiens. He is a fuzzy orange thing who loves baseball, but is pretending he loves hockey, and as such has a permanent frown on his face.

During the Canadiens-Rangers series, Youppi made a bet with Jimmy Fallon stipulating that if the Habs lost, he’d take 10 pictures in a Rangers jersey and ride a mechanical bull. Sunday, he paid up.

Warning: Do not look at these photos if you do not like incredibly sad things.

okay that's not that sa-

oh jeez

he’s in front of his old stadium crying

this is youppi!‘s way of getting drunk and texting his ex-girlfriend

oh no oh no why why

HE JUST SAID YOU HAVE TO TAKE PHOTOS. HE DIDN'T SAY THEY HAD TO BE SAD CAROUSEL PHOTOS

just play some damn sarah mclachlan already

okay this one isn't that sad again

I hope those kosher meats cheer you up, Youp.

make it stop only one more make it stop And here he is, being sad on the mechanical bull.

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