Anyone who has followed the overlap between hip hop and sports over the last decade and a half has likely heard of “the Drake curse.” The idea suggests that whenever he places a high profile sports bet, the outcome rarely goes his way. Unfortunately for Jake Paul, that reputation held up once again when Anthony Joshua stopped him with a knockout in the sixth round of their Netflix streamed boxing bout on Friday, December 19.
As reported by AllHipHop, the Toronto superstar had placed a $200K wager on Jake Paul to pull off the upset against Joshua. If Paul had won, the bet would have paid Drake an estimated $1.64 million. Few boxing fans expected that outcome, though, so the gamble itself was not especially shocking. For someone who regularly makes big money plays and has plenty of resources to fall back on, the loss likely did little more than bruise his pride.
It is also unlikely that this result will change Drake’s approach to betting anytime soon. He has never been one to shy away from taking chances, often valuing the thrill of the game over the return. Jokes about his so called curse continue to circulate, yet he has shown no interest in slowing down. In the grand scheme, losing sums that would change most lives barely registers for him.\
Jake Paul, meanwhile, does not appear overly shaken by the defeat. He revealed that he underwent surgery to repair a broken jaw sustained in the fight with Joshua. Shortly after, he went as far as calling out Canelo Alvarez for a potential matchup just over a week later.
On Drake’s side, the loss came as he continues to take other calculated risks. As a Stake partner, he recently rolled the dice on the rollout of his ICEMAN album, hosting livestreams that could have easily gone wrong from a technical standpoint. Instead, the strategy energized his fanbase, with one final stream still expected ahead of the project’s release, setting the stage for what looks like a busy 2026.
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
Away from music and sports betting, Drake is also navigating legal developments connected to the appeal of his dismissed defamation lawsuit against Universal Music Group. That situation has temporarily slowed down, as the Court of Appeals pushed mediation for both sides into early next year, giving everyone involved a pause over the holidays.
Interestingly, this is far from the first time Drake and Jake Paul have crossed paths through betting. Paul previously lost after Drake backed him against Tommy Fury, Drake missed when he picked Mike Tyson to beat Jake, and he also came up short when he wagered on Nate Diaz to defeat Paul. The pattern only adds to the mythology that continues to follow Drake whenever money is on the line.
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