Drake placed a $200,000 wager on Jake Paul defeating Anthony Joshua, but the infamous ‘Drake curse’ seemed to strike once more.
In reality, a match between a YouTuber and a former heavyweight champion is quite a mismatch, and it played out as expected with the British boxer knocking out Paul in the sixth round.
After the fight, Paul found himself spitting blood and speculating if Joshua had broken his jaw.
“Anthony’s a great fighter, I got my ass beat, but that’s what this sport’s about,” Paul commented. “I think my jaw is broken by the way.
“Yeah, it’s definitely broken. But man, that was good. A nice little a** whipping from one of the best to ever do it.
“I love this so I’m going to come back and get a world championship belt at some point.”
Paul later confirmed that his jaw had suffered two breaks.
Given the clear disparity in experience, Joshua was favored to win, but Drake’s bet on Paul compounded the odds against him.
For those unfamiliar, the Canadian rapper has a history of losing significant bets, prompting online jokes that he might have jinxed Paul’s chances.
Drake, who placed the $200,000 bet on Stake, referred to his hopeful ‘biggest upset in sports history’ wager: “Jakeyyyyy boy. Lock in.”
The Drake curse continues 😂😂😂#JakeJoshua pic.twitter.com/gXPkxW5AEP
— Mosheki Daniel (@MoshekiD) December 20, 2025
Previously, Drake risked $565,000 on Tyson Fury to beat Oleksandr Usyk in May 2024, but it was Usyk who emerged victorious.
In another instance, the Toronto rapper lost $355,000 last November after predicting Mike Tyson would defeat Paul; instead, the YouTuber won against the former heavyweight champion by unanimous decision.
Despite appearances, Drake isn’t completely unlucky with bets. According to a site analyzing this supposed ‘curse,’ he is actually $413k ahead from his public bets on sports events.
From 82 bets shared publicly, the 39-year-old has wagered an astonishing $35.75 million, achieving a return of $36.17 million.
Drake’s greatest betting success is in the NFL, with a $1.68 million profit. Conversely, he is $1.90 million down on soccer bets.
Among all sports, Drake seems to favor betting on the UFC, with 25 public wagers.