Drake, the globally renowned Canadian superstar, has lost a $355,000 bet after Mike Tyson was defeated by Jake Paul.

The rapper had posted a screenshot of the wager on Instagram just before the fight took place.

However, the bet didn’t go in his favor as Jake Paul triumphed over Tyson by unanimous decision in an eight-round heavyweight bout at AT&T Stadium in Arlington, Texas, on Friday.

Had Tyson won, Drake would have walked away with $1,000,000.