Drake has never been shy about his love for high-stakes gambling, and now he’s revealing his biggest win yet. In a recent promo video for Stake, the online betting platform he endorses, the rap superstar opened up about his most unforgettable victory.
Drake’s Insane $40 Million Win
When asked about his largest gambling payout, Drake laughed and jokingly called it a “tax question.” He then recalled a wild night at Dave & Buster’s that led to an unbelievable fortune.
“I was getting this random girl to call roulette numbers, and I hit, like, eight out of 10 numbers,” Drake said. “By the end of the night, we had won like $38 million, $40 million. Yeah, $40 million.”
Describing the night as “the craziest ever,” the Toronto rapper emphasized how surreal the experience was. “January of 2024 was crazy. There’s not even a word for it.”
Betting Against Michael Jordan
Aside from roulette, Drake has also tested his luck against some legendary competitors. One of his most intense gambling sessions, he revealed, was against NBA icon Michael Jordan.
Drake recalled an unforgettable night during All-Star Weekend in Toronto, where he and MJ faced off in an intense ping pong match—each round coming with high stakes.
“He just wouldn’t leave the ping pong table,” Drake said. “He kept betting bands. Like, 10 bands, 20 bands. He kept betting ’cause he just couldn’t stomach the loss.”
Despite the fierce competition, Drake admired Jordan’s relentless drive, calling him “the gambling G.O.A.T.” “He’s definitely not a quitter,” the rapper added.
Drake’s High-Stakes Gambling History
While Drake has celebrated major wins, he’s also suffered some huge losses.
- In 2023, he placed a $355,000 bet on Mike Tyson to defeat Jake Paul—only to watch Tyson lose by unanimous decision.
- In 2022, he lost $2 million after backing Israel Adesanya against Alex Pereira in a UFC bout.
Despite the losses, one thing is clear: Drake loves the thrill of gambling, and he has the bankroll to keep playing.
