Drake's penchant for gambling has been well-known, yet even for someone accustomed to placing high-stakes bets; his latest tale sounds almost too weird to be true. In a just-released video ad for the online casino Stake, the Toronto-born rap superstar relayed one of the wildest nights of his life to hit a jaw-dropping $40 million jackpot at none other than Dave & Buster's.
Surreal stuff, man Drake revealed that the jaw-dropping win occurred in January 2024, and it all began with a stranger. He was playing roulette when he asked an unknown woman to call out numbers for him. What happened next was nothing short of phenomenal.
"The biggest win I ever had. I was in Dave & Buster's," Drake added. "I was getting this random girl, a girl, to call out all these roulette numbers for me. I hit probably eight out of 10 numbers, and I believe we won by the night's end. Like, 38 million? 40 million? Yeah, $40 million. "It's crazy, the craziest night ever gambling for sure. January, January of 2024."
It's unclear whether the woman received money for her good fortune; she was present for one of the most legendary gambling nights in hip-hop history. Drake's relatives seemed to be playing roulette between Big Roller and oafish.
This isn't Drake's first time in the news over his high-roller lifestyle. The "God's Plan" rapper is no stranger to placing jaw-dropping bets, a pattern that leads to both monumental wins and crushing losses.
One of his notable wins was when he turned $220,000 into $17.9 million in a single roulette spin in May 2022. A few months later, he won over $24.9 million while playing roulette with rapper French Montana. He's also hit big on sports betting, winning $3.2 million on a series of UFC London fights in July 2022 and $2.7 million backing Israel Adesanya in April 2023.
But he has not bet on every gamble to his advantage. Drake has also taken multi-million-dollar hits, including nearly $25 million during a casino session with French Montana and $2 million on a losing wager on Adesanya at UFC 281. In addition, he was dealt a $1.6 million loss when Adesanya was defeated by Alex Pereira in November 2022, a $1 million loss on the 2022 FIFA World Cup Final, and $700,000 on a single NBA/NHL betting spree montre, Unpacking the Stake footage, Drake saluted the legend: the real-life gambling G.O.A.T. NBA legend Michael Jordan.
The real-life gambling G.O.A.T., in my humble opinion, is a controversial take, but honestly to God, Michael Jordan, probably," Drake said.
He even remembered his brush with MJ on an All-Star Weekend in Toronto, when he claimed to have beaten Jordan in ping-pong.
"He was just betting bands after bands," Drake chuckled. "10 bands, 20 bands, like, just kept betting because he just couldn't stomach the loss."
Drake gambling stories are always legendary, whether it's the roulette wheel, some sports bets, or even a friendly ping-pong bet with a basketball king. Oh, but as nights to remember go, it's hard to beat a $40 million jackpot at Dave & Buster's.
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