In Paul’s highly controversial fight against Mike Tyson last November, Drake wagered a huge $355,000 bet on Tyson to beat the YouTuber turned boxer, subsequently losing his money. However, after going ...

Drake has lost of $500,000 betting on Jake Paul. Paul's latest match was against former heavyweight champion Anthony Joshua.

Drake was confident that Jake Paul could pull off an upset victory over Anthony Joshua in their heavyweight boxing match on Friday night. He was so confident, in fact, that he posted an image of a ...

Drake has placed a major wager on Jake Paul to defeat former heavyweight champion Anthony Joshua, inserting a significant financial layer into an already high-profile boxing match. The size of the bet ...

Jake Paul’s loss to Anthony Joshua added another chapter to the “Drake curse” saga after the rapper’s $200,000 bet failed to deliver a win. Drake watched his $200,000 bet crumble Saturday night as ...

Drake’s reputation as a terrible sports bettor remained intact Friday after he showed his personal pick for the Jake Paul-Anthony Joshua fight. Drake posted a bet slip on his Instagram story hours ...

Drake is once again putting serious money behind a high-profile fight, this time backing Jake Paul with a massive wager ahead of his matchup against Anthony Joshua. On Friday (Dec. 19), the Toronto ...

Grammy-award-winning artist Drake is unloading his wallet ahead of Jake Paul vs. Mike Tyson. Drake is no stranger to taking massive risks on and off the mic. Ahead of Jake Paul vs. Mike Tyson, one of ...