Drake Dry Snitches On Michael Jordan’s Gambling Skills
Written by djfrosty on March 24, 2025
It’s not a secret that Michael Jordan is an avid gambler, even if there’s been a scarcity of detailed stories revealed. But Drake unveiled a battle that he had with the NBA legend in an interview for Stake, the online casino and sports betting company. Drake has a longstanding endorsement deal with Stake. The Honestly, Nevermind artist shared how he wound up in a tight battle over ping-pong with Jordan in the video, which was posted via Instagram last Thursday (March 20).
“He’ll gamble on anything. I think it was All-Star Weekend in Toronto and he had an event to be at, and I beat him at ping pong a couple of times,” he recalled. Drake referred to the former Chicago Bulls guard as his “gambling G.O.A.T.” before adding: “He just wouldn’t leave the ping pong table. He just kept betting bands. Like, 10 bands, 20 bands. He kept betting ’cause he just couldn’t stomach the loss. He’s definitely not a quitter. I respect him deeply for his gambling nature.”
The interview initially began with Drake being asked about the biggest win he ever had in gambling. The first question simply asked the Canadian superstar what his biggest win was. “Fuck… tax questions,” he responded while laughing. “The biggest win I ever had, I was actually in Dave & Busters — and this is [a] testament to playing in a brick-and-mortar casino versus playing on Stake. I was getting this random girl to call roulette numbers and I hit, like, eight out of 10 numbers. I think by the end of the night, we had won like $38 million, $40 million. Yeah, $40 million.” Drake continued, “It was crazy. The craziest night ever gambling, for sure. January of 2024 was crazy. There’s not even a word for it.”
Drake’s gambling adventures have become a much-discussed topic among Hip-Hop fans, particularly his losses. He lost $355,000 betting on Mike Tyson to beat influencer-turned-brawler Jake Paul. Paul won the fight by unanimous decision, thwarting a potential million-dollar payday. Drake also lost a reported $2 million by betting on Israel Adesanya to defeat eventual victor Alex Perreira in their UFC bout in 2022.
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