Drake experienced a remarkable $40 million win while gambling at Dave and Buster’s in January 2024, and he revealed the story in a new promotional video for the online casino Stake that was released on March 20. During the unforgettable night, the music star credited an anonymous woman as his lucky charm while playing roulette, helping him hit numerous winning numbers. This win was one of his largest victories, with Drake expressing excitement over the $40 million triumph.

Drake has a reputation for engaging in high-stakes gambling activities, with both impressive wins and significant losses in his gambling record. Notable achievements include earning $17.9 million from a single roulette spin in May 2022, as well as winning over $24.9 million while playing alongside rapper French Montana a couple of months later. Additionally, he successfully wagered $3.2 million on UFC London bouts in July 2022 and earned $2.7 million by supporting UFC fighter Israel Adesanya in April 2023. However, he also encountered substantial losses, including reportedly losing almost $25 million during a casino session with French Montana and betting $2 million on Adesanya at UFC 281, among others.

In the promotional video, Drake discussed his admiration for basketball legend Michael Jordan's gambling skills, labeling him as the ultimate betting champion. Drake fondly recalled an instance where he defeated Jordan in a ping pong match during an All-Star Weekend in Toronto, with Jordan continuously offering larger bets while being unable to accept defeat gracefully.