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Canadian rapper Drake is not afraid to put his money where his mouth is when it comes to placing massive bets on sporting events. 

The former heavyweight champion of the world Mike Tyson and YouTuber-turned professional boxer Jake Paul faced off on Friday night. The long-awaited fight garnered considerable interest and attracted a high volume of wagers.

Drake was confident the 58-year-old Tyson would be able to prevail in the match against the 27-year-old Paul and placed a wager of a few hundred thousand dollars on “Iron Mike.” But, Paul ultimately defeated Tyson in a unanimous decision. 

Jake Paul after being Tyson

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In a social media post, Drake showed his $355,000 bet on Tyson to win, which was made at +285 odds. Given those odds, the five-time Grammy winner would have been in line for a pay out of around $1 million dollars.

Drake was not the only notable person to lose a hefty sum following the fight’s outcome. UFC star Conor McGregor said he put down a total of $1 million on fights that were scheduled for this weekend.

Jake Paul and Mike Tyson head to head

One of McGregor’s wagers was for Tyson to win against Paul. He also placed a bet on Saturday’s UFC 309 event between Jon “Bones” Jones and Stipe Miocic. 

After Friday’s fight, Paul was asked about the possibility of a fight between him and McGregor in the future. “Yeah, he’ll never do that, though,” Paul said, before his manager Nakisa Bidarian jumped in and said, “One, he’s under contract. And two, he won’t do that. He knows better.”

The Tyson-Paul bout was also plagued by buffering issues. The bandwidth problems raised some concerns about Netflix’s ability to provide steady streams for NFL games this Christmas. 

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