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Rb Hip Hop

Drake on Playing Ping-Pong With Michael Jordan: ‘He’ll Gamble on Anything’

The Toronto rapper said Jordan wouldn't leave the table until he won.

Drake attends the Toronto Raptors and the Sacramento Kings basketball game at the Scotiabank Arena on Nov. 2, 2024 in Toronto, Canada.

Drake attends the Toronto Raptors and the Sacramento Kings basketball game at the Scotiabank Arena on Nov. 2, 2024 in Toronto, Canada.

Mark Blinch/Getty Images

It’s no secret that Drake enjoys gambling, and his partnership with Australian online gambling company Stake is a testament to that.

The Toronto rapper posted of clip of him sitting down with the company for their online series House Money, where he answered questions about his biggest win and his gambling GOAT.


When asked about his biggest win, Drake revealed that he once won around $40 million playing roulette one night while in Dave & Buster’s. “I was getting this random girl to call roulette numbers for me,” he said. “I hit like eight out of 10 numbers and I think by the end of the night, we had won like $40 million. It was crazy. The craziest night ever gambling for sure. I remember getting back to my hotel, we were still winning.”

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Drake then talked about playing intense games of ping-pong with Michael Jordan during All-Star Weekend in Toronto one year. “Controversial take, but probably Michael Jordan,” he said with a laugh. “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 a couple times and he just wouldn’t leave the ping-pong table. He kept just betting me, like, bands. 10 bands, 20 bands. Just kept betting because he just couldn’t stomach the loss, you know? He’s definitely not a quitter. I respect him deeply for his gambling nature. So, yeah, I’d say Michael Jordan’s definitely one-of-one.”

In other Drake news, his joint album $ome $exy $ongs 4 U with PartyNextDoor currently sits at No. 3 on the Billboard 200 and his lawsuit against UMG is in full swing.

This article was first published by Billboard U.S.

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EMPIRE's Tina Davis (left) and Girl Connected's Lola Plaku at Conversations with the Pros at Toronto Metropolitan University in Toronto on March 28, 2025.
Courtesy of Girl Connected

EMPIRE's Tina Davis (left) and Girl Connected's Lola Plaku at Conversations with the Pros at Toronto Metropolitan University in Toronto on March 28, 2025.

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EMPIRE President Tina Davis Gives Strategic Advice to Women in Music at Girl Connected's New Speaker Series

On Friday (March 28), the president of EMPIRE, the Bay Area-independent label and music company, came to Toronto for Conversation with the Pros offering tangible advice to the mentorship program's community. Davis also spoke to Billboard Canada about her impressive journey in the industry.

Girl Connected has launched a new series that connects the next generation of women in Canadian music with powerhouse executives for the global industry.

On Friday (March 28), Tina Davis, president of EMPIRE, sat down with Girl Connected founder and music industry veteran Lola Plaku at Toronto Metropolitan University for the first in-person Canadian edition of Conversations with the Pros (Billboard Canada was a supporting partner). The series brings in inspiring music industry figures from Girl Connected's international network to talk about their journeys and offer actionable information and advice to help the budding music professionals develop their skills and reach the next level of their careers.

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