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Drake Opens Up About Wildest Betting Moments: “$40 million” at ‘Dave & Busters’

March 22, 2025
Sourcestaff

We all know Drake has always been open about his passion for gambling, and now he’s sharing the story behind his biggest win. For the record, the Drake gambling curse is NOT a real thing. Read on …

In promotional content for Stake, the online betting platform he’s partnered with, the Toronto born rap icon took fans inside one of his most memorable gambling nights.

Get this: when asked about his most significant win, Drake couldn’t help but laugh, calling it a “tax question.” That part.

He then dove into the details of a crazy night at Dave & Buster’s that led to a staggering payout.

We’re talking Dave & Busters. Not Monte Carlo or Macau, but Dave & Busters.

“I was getting this random girl to call roulette numbers, and I hit, like, eight out of 10 numbers,” Drake recalled. “By the end of the night, we had won like $38 million, $40 million. Yeah, $40 million.” The star described the experience as “the craziest night ever gambling,” adding, “January of 2024 was crazy. There’s not even a word for it.”

$40 million at Dave & Busters. Basically hit a Powerball ticket.

But wait, in addition to his personal wins, Drake also reflected on a memorable betting session with NBA legend Michael Jordan, who Drake refers to as his “gambling G.O.A.T.” The two went head-to-head in a fierce ping pong match during All-Star Weekend in Toronto, with MJ not backing down easily. “He just wouldn’t leave the ping pong table,” Drake shared. “He kept betting bands. Like, 10 bands, 20 bands. He kept betting ’cause he just couldn’t stomach the loss.” Despite the competitive tension, Drake admired Jordan’s drive, saying, “He’s definitely not a quitter.”

Of course, Drake’s betting adventures haven’t always gone his way. Last year, he placed a $355,000 bet on Mike Tyson to defeat Jake Paul, only to watch Tyson lose by unanimous decision. He also lost $2 million in 2022 after backing Israel Adesanya in a UFC match against Alex Pereira.

Those so-called Drake curse losses seem like peanuts compared to that Dave & Busters win, which would possibly keep him up for a long time.