Jake Paul scored a unanimous decision victory over Mike Tyson in the boxing ring on Friday (Nov. 15), and Drake’s wallet took a hit because of it.
“I’m late, but I’m here [with] money on the line for today and [tomorrow]. Stake, I need some dubs,” Drake captioned his Instagram post alongside a screenshot of the wager. If things had gone his way, the payout would’ve topped $1 million.
Paul’s win, although bittersweet for many, wasn’t exactly surprising given the 30-plus-year age gap between him and Tyson. Not to mention, the boxing legend made the odds less favorable in his two sanctioned fights with Kevin McBride and Danny Williams in 2005 and 2004, respectively.
On the other hand, Paul is coming off of wins against Mike Perry and Ryan Bourland earlier in the year. During Friday’s post-match conference, the social media personality admitted to holding back. “I wanted to give the fans a show, but I didn’t want to hurt someone [who] didn’t need to be hurt,” he shared. "I tried to give the best fight I possibly could, but when someone’s just surviving in the ring, it’s hard to make it exciting. I couldn’t really get him to engage me or slip shots and do something super cool or whatever.”
As for Drake, his luck in betting against Paul seems to be running cold. In August 2023, he wagered $250,000 on Nate Diaz defeating the YouTuber-turned-boxer in Dallas. Then, in February of the same year, the Canadian rapper put $400,000 on Paul taking out Tommy Fury, only for the latter fighter to win by a split decision.
On the music side, Drake unloaded “No Face” featuring Playboi Carti, “SOD” and “Circadian Rhythm” in August. It served as the Grammy Award-winning artist’s second three-pack following his much-talked-about feud with Kendrick Lamar.