Drake Talks Biggest Gamble and Ping Pong Bets with Michael Jordan

Drake is no stranger to the world of sports betting, and this time, he's opening up about his biggest gambling win ever. In a video promo for Stake, the platform he's been endorsing for a while, posted on Instagram Thursday (March 20), Drake answers a bunch of questions about his love for gambling.

When asked about his biggest win, he chuckled and said, “F---… tax questions.” But then, he got serious. “The biggest win I ever had, I was actually in Dave & Busters — and this is testament to playing in a brick-and-mortar casino versus playing on Stake,” he explained. “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.”

He added, “It was crazy. The craziest night ever gambling, for sure. January of 2024 was crazy. There’s not even a word for it.”

But wait, there's more. Drake also shared a wild story about his gambling encounter with NBA legend Michael Jordan, whom he refers to as the “gambling G.O.A.T.” The two got into a fierce game of ping pong with some serious money on the line. “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,” Drake recalled. “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.”

Even with those huge wins at Dave & Busters and against MJ, Drake has had his fair share of tough losses in the world of high-stakes gambling.

Check out the promo here.