Drake Confirms Michael Jordan Gambling Rumors

The many stories of NBA Hall of Fame legend Michael Jordan being a big gambler have been substantiated over the years and Canadian rapper Drake just added another story to what people have been saying about the former Chicago Bulls All-Star.

In a recent video clip posted by RapTV on social media, Drake tells a story about going up against who many feel is the greatest NBA player of all time several years ago. The “OVO (October’s Very Own)” label owner claims that he was beating Jordan in ping-pong but the oft-talked-about competitive nature of Jordan appeared in a big way.

Drake explains that it took place during All-Star Weekend when the game was being played in Toronto (2016). He said that after beating the legend, he “wouldn’t leave the ping-pong table” and kept betting against Drake, to the tune of tens of thousands of dollars.

“Gambling GOAT? To me? Controversial take but Michael Jordan,” Drake stated. “He’ll gamble on anything. I think I remember it was All-Star Weekend in Toronto, and he had an event to be at. I beat him at ping-pong, like, a couple times, and he just wouldn’t leave the ping-pong table. He kept just betting me, like, bands. 10 bands, 20 bands.”

Drake did not state if Jordan ever won or how much money he did eventually lose or won back, but he spoke of the constant betting that went on, eluding to Jordan making more bets, signifying that Drake may have beaten Jordan more times than he would have liked.

“Just kept betting because he just couldn’t stomach the loss, you know? He’s definitely not a quitter,” Drake continued.

Drake stated he appreciated his “gambling nature” and determined that the G.O.A.T. (Greatest of all time) was one of the best gamblers to add to what’s been said about Jordan throughout his playing and retirement years.

“I respect him deeply for his gambling nature. So, yeah, I’d say Michael Jordan’s definitely one of one.”

Drake reveals during an interview with Stake that he beat Michael Jordan for over $20k in ping pong 🏓 👀 pic.twitter.com/xQZ46sgKbU

— RapTV (@Rap) March 22, 2025