Nov 17, 2023; Toronto, Ontario, CAN; Recording artist Drake wears headphones to conduct an in-game media interview while watching the Toronto Raptors host the Boston Celtics at Scotiabank Arena. Mandatory Credit: Dan Hamilton-USA TODAY Sports via Imagn Images

Link Copied to Clipboard!

Anthony Joshua knocked Jake Paul out six rounds into their boxing match, blocking Drake and other Paul supporters from a big payout.

If you have been around hip-hop and sports culture over the past 15 years, you may have heard about “the Drake curse.” It’s the presumption that his constant betting, specifically in sports, doesn’t turn out well for whatever he’s betting in favor of. Sadly for Jake Paul, this turned true when Anthony Joshua knocked him out in the sixth round of their Netflix-streamed boxing match last night (Friday, December 19).

As caught by AllHipHop, the Toronto superstar had bet $200K on him to defeat Joshua, which would’ve netted Drizzy a whopping $1.64 million if Paul had won. Of course, not many in the boxing world expected him to do so. As such, for a high-stakes player like the 6ix God, his risk shouldn’t come as much surprise. Also, it’s not like he doesn’t have millions of other dollars at his disposal to wipe his gambling-afflicted tears away.

Still, we doubt Drake will change his betting ways anytime soon, because he prioritizes the love of the game over any potential rewards. Jokes about his “curse” continue to ring off, yet he never chose to slow down. At the end of the day, The Boy’s fine with losing more money than most people make in a year.

Drake Bets On Jake Paul

Dec 19, 2025; Miami, Florida, UNITED STATES; Jake Paul looks on after losing against Anthony Joshua during a heavyweight boxing bout at Kayesa Center. Mandatory Credit: Sam Navarro / USA TODAY NETWORK via Imagn Images

However, Jake Paul isn’t breaking much of a sweat over this. He revealed he got surgery for the broken jaw he left the Anthony Joshua fight with, and he challenged Canelo Alvarez to fight in just a little over a week.

As for the Stake partner who unsuccessfully bet on Paul to win, Drake’s taking a risk with his ICEMAN album. His livestreams for its rollout could’ve been technically disastrous, but it seems to have paid off for his very excited fanbase. We’re still waiting on the final one before the LP comes out, and it seems like 2026 will be the year.

Elsewhere, Drake’s also dealing with legal updates in his dismissed UMG defamation lawsuit’s appeal. Well, actually, he won’t be having to deal with them as much these days. The Court of Appeals delayed both parties’ mediation to early next year, giving everyone a substantial holiday break.

Ironically enough, though, this isn’t these two’s only betting crossover. Jake Paul lost after Drake bet on him to beat Tommy Fury, Drizzy lost his bet on Mike Tyson beating Jake, and he lost his bet on Nate Diaz to beat Paul.