Drake and gambling . These two things go together like peanut butter and jelly or maybe more like champagne and diamonds for the 6 God. We all know Drake loves to bet big and he's definitely not shy about sharing his wins and losses. Recently he spilled the tea on his biggest gambling victory ever and let's just say it involves a random girl some roulette and a whole lot of cash. But that's not all folks because Drake also shared an epic gambling story involving none other than the legend himself Michael Jordan and it involves Ping Pong!
Drake's Wildest Gambling Night: $40 Million at Dave & Buster's Seriously?
When asked about his biggest win Drake didn't hold back. In a promo video for Stake the betting platform he reps he laughed and said it was kind of a "tax question". Then he dove into the story of one truly unbelievable night at Dave & Buster's of all places.
Apparently Drake had this "random girl" calling out roulette numbers for him. Sounds like a movie scene right? Well it worked like magic! Drake says he hit "like eight out of 10 numbers". By the end of the night the winnings were just mind-blowing . He estimates they walked away with around "$38 million $40 million. Yeah $40 million." Can you even imagine? Drake called it "the craziest night ever gambling " saying January 2024 was just unreal for him. He even remembers getting back to his hotel and still feeling like they were on a winning streak.
Drake vs. Michael Jordan: The Ping Pong Gambling Showdown You Had to See to Believe

But the gambling story that really caught our attention? Drake's tale about playing ping pong with Michael Jordan . Yes THE Michael Jordan. Drake calls MJ his "gambling G.O.A.T." and after hearing this story you might agree.
It all went down during All-Star Weekend in Toronto. Drake and Jordan faced off at the ping pong table and things got intense fast. Drake says he beat Jordan a couple of times and MJ was not having it. "He just wouldn’t leave the ping pong table" Drake recalls. Jordan kept betting Drake getting more and more competitive with each game. Drake remembers Jordan betting "bands" like $10000 then $20000 a game! Just trying to win back his losses. Drake admired Jordan's hardcore competitive spirit saying "He’s definitely not a quitter. I respect him deeply for his gambling nature." It just goes to show even legends like Michael Jordan hate to lose especially when there's a bet on the table even if it is just ping pong.
Drake's Gambling Rollercoaster: Big Wins and Painful Losses It's All Part of the Game

Of course it is not always wins for Drake in the gambling world. He's had his share of losses too. Remember last year when he bet a massive $355000 on Mike Tyson to beat Jake Paul? Yeah that did not go as planned. Tyson lost and Drake lost a ton of cash. He also lost a cool $2 million back in 2022 betting on a UFC fight. Despite the losses though Drake clearly loves the thrill of high Stakes betting. And let's be real he has probably got the bankroll to handle a few ups and downs.
Drake's Gambling Adventures: Key Takeaways

- Biggest Win Ever: Drake claims his largest gambling win was around $40 million playing roulette at Dave & Buster's in January 2024.
- Roulette Strategy: His winning strategy involved having a "random girl" call out roulette numbers.
- Ping Pong with MJ: Drake played ping pong with Michael Jordan during All-Star Weekend in Toronto and gambled with him MJ kept betting bigger amounts because he hated to lose.
- Jordan's Gambling G.O.A.T Status: Drake considers Michael Jordan his "gambling G.O.A.T." due to his competitive nature and willingness to bet on anything.
- Big Losses Too: Drake has also experienced significant gambling losses including a $355000 bet on Mike Tyson and $2 million on a UFC fight.
Drake and MJ: Just Two Super Competitive Guys Who Happen to Gamble (and Play Ping Pong)

So there you have it. Drake's gambling stories are always entertaining whether he is winning millions at Dave & Buster's or battling Michael Jordan in a high-stakes ping pong match. It is clear Drake loves the game and he is not afraid to bet big. And his story about Michael Jordan just proves that even the greatest athletes in the world have that competitive fire especially when there is a little friendly wagering involved. Who knows what wild gambling tales Drake will share next? We will definitely be listening.