Drake Says This NBA Star Is The ‘Gambling GOAT’

Drake recently revealed that he once won $40 million at Dave & Buster’s while gambling on roulette.

In a promotional video for the Australian online casino Stake, Drake opened up about some wild experiences he’s had gambling in the past. Aside from winning $40 million at the popular restaurant chain, the “Family Matters” rapper also spoke about wiping an NBA champion of thousands after beating him during a ping-pong match.

Since Drake is a partner with the online casino Stake, the rapper occasionally appears in promotional videos for the company.

In one ad, reported by Complex, the “Only” performer shared who he believed the “real-life gambling GOAT (greatest of all time)” was.

He started his answer by saying it would be controversial before revealing that Michael Jordan would “gamble on anything.”

Drake recalled one NBA All-Star weekend in which he beat Jordan at ping-pong. According to him, Jordan “just wouldn’t leave the ping-pong table.”

“He just kept betting me, like, bands,” said Drake. “10 bands, 20 bands. Just kept betting because he just couldn’t stomach the loss, you know?”

Drake, 38, praised Jordan for his relentlessness, adding, “I respect him deeply for his gambling nature.”

Although Drake won several thousand betting Jordan in ping-pong, that doesn’t even scratch the surface of his biggest victory.

Elsewhere, during his promotional ad, the father of one opened up about a “crazy” night he had at Dave & Buster’s in which he hit “like eight out of 10 numbers” playing roulette.

“I think by the end of the night, we had won like 38 million? 40 million? Yeah, $40 million,” he said.

Drake continued: “It’s crazy, the craziest night ever gambling for sure. January of 2024, it was crazy. That’s not even the word for it.”

After his massive win at Dave & Buster’s, Drake won another couple million dollars betting on the Kansas City Chiefs during Super Bowl LVIII.

On February 10, 2024, the “Rich Flex” rapper posted a screenshot of his Stake bet slip, showing he wagered $1,150,000 on the Chiefs to win.

“I can’t bet against the swifties,” he wrote, referencing Taylor Swift’s highly-publicized relationship with Chiefs’ tight-end Travis Kelce.

As reported by PEOPLE, the Grammy winner also shared his wager in his Instagram Stories and told his followers that he’d be blessing a fan during a concert.

“If I win, somebody getting super blessed at the show tmrw,” he wrote.

Despite his big wins, Drake’s 2024 started going downhill after he became embroiled in a rap battle with Kendrick Lamar.

The two powerhouse musicians released several tracks about each other; however, Lamar was declared the winner once he dropped the Billboard Hot 100 chart-topper “Not Like Us.”

The song became a viral hit and slammed Drake for being an alleged “pedophile.” Lamar even performed the song live during Super Bowl LIX in 2025.

Weeks before his performance, Drake filed a lawsuit against Universal Music Group (UMG), claiming the music distributor paid to boost Lamar’s song to the top of streaming charts.

The lawsuit alleged that UMG prioritized “corporate greed over the safety and wellbeing of its artists” by distributing “Not Like Us” and claimed they spread “false factual allegations” against Drake.

Drake’s legal team also commented on the shocking lawsuit and shared bold claims about the company.

Michael J. Gottlieb accused UGM of being a “greedy company” that cared more about “profiting from dangerous information” about its artist rather than defending the truth.

Drake’s attorney also mentioned how dangerous the rap battle had become, referencing the security guard who was shot outside of the rapper’s home in Canada.

The security guard reportedly suffered gunshot wounds to his chest and was rushed to the hospital for emergency surgery.

UMG responded to Drake’s lawsuit, vehemently denying his accusations and pointing out that he owes them a good chunk of his success.

“Not only are these claims untrue, but the notion that we would seek to harm the reputation of any artist – let alone Drake – is illogical,” a spokesperson for the company said.