Canadian rapper Drake loses big on Youtuber Jake Paul again

William Demamp
December 20, 2025
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Drake loses $200k on Jake Paul fight at Stake.com

Canadian musician Drake has lost $200,000 betting on Youtuber-turned-boxer Jake Paul to defeat former World Champion Anthony Joshua. 

The One Dance singer shared a Stake.com bet slip on December 19, showing he stood to win $1.6million if Paul could cause a massive boil-over at odds of 8.20. 

But Joshua was in a different class to Paul and ultimately ended the bout in the sixth round with a slick cross, and in the process, barely put a dent into Drake’s estimated $250million net worth. 

“It wasn’t the best performance,” Anthony said. 

“I wanted to pin him down and hurt him. It took me longer than I expected.”

While Joshua was complimentary of Paul after the fight, it was clearly a big step up for the controversial American after defeating a man half his size Julio Cesar Chavez Jr and ancient Mike Tyson in his previous two fights. 

Drake had previously made headlines after betting $355,000 on Tyson to defeat Paul, but 59-year-old looked a shadow of the fighter he was, and the fight barely got out of first gear, and Paul ultimately won. 

Drake has been in the headlines before for his gambling exploits, with the hitmaker once telling reporters about a night on the roulette tables, where his crew walked out with close to $40million. 

Drake is an ambassador for Stake.com, with the sports betting site and online casino enlisting high-profile names to promote the website across social media channels and via streaming platforms. 

Author William Demamp

Born in Ontario, Canada, William is one of the founders of the World Gambling List and an experienced professional punter. Specialising in sports betting, William has a special spot in his heart for NFL, ice hockey and football.

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