Drake, Gambling, and $40 Million: Who’s the Real ‘Gambling GOAT’ in Showbiz?

Who’s the ‘Gambling GOAT’? Drake has an answer

In a promo video for the online casino Stake, Drake didn’t hesitate when asked who the greatest gambler of all time was. According to him, it’s Michael Jordan — not because he placed the biggest bets, but because he’ll bet on absolutely anything.

“He just couldn’t handle losing. He kept betting — 10 grand, 20 grand… he just wouldn’t leave the table,” Drake recalled, describing a ping-pong match during an NBA All-Star Weekend.

Drake said Jordan’s persistence and refusal to walk away, despite losing repeatedly, made him the true icon of the gambling world in his eyes.

How Drake ‘cleaned out’ Dave & Buster’s for $40 million

Drake’s most headline-worthy story wasn’t the ping-pong match, but a wild night playing roulette. In January 2024, he said he hit eight out of ten numbers during a roulette session at Dave & Buster’s and ended up winning $40 million.

“It was insane. The craziest night ever, no doubt. We won like 38, maybe 40 million. Just nuts,” he said.

Considering Dave & Buster’s is not a casino, the huge figure suggests it was most likely a private event — possibly set up by Stake — where the venue acted as the setting for high-stakes play.

Another win: $2.3 million on the Super Bowl

Drake doesn’t just gamble at the roulette table. He also places major bets on sports. For Super Bowl LVIII, he placed a $1.15 million bet on the Kansas City Chiefs, which paid out $2.3 million.

In his Instagram post, he offered a simple explanation:

“I can’t bet against the Swifties,” referencing Taylor Swift’s relationship with Chiefs tight-end Travis Kelce.

He posted a screenshot of the Stake betting slip and even promised that if he won, a fan at his next show would receive a generous gift. He won — so someone definitely got “super blessed.”

Strategic gambling: building a brand through high-stakes play

For Drake, gambling isn’t just entertainment — it’s part of his personal brand. His bets become stories, content, and ultimately — marketing assets. Here’s how it works:

• They drive media coverage and viral moments.
• They tie his brand to pop culture icons like Jordan and Swift.
• They create audience engagement through giveaways and promises.
• They promote his partnership with Stake — seamlessly blending business and image.

Let’s break it down in a simple table:

In other words, every win is a media campaign in disguise.

Quotes that capture Drake’s gambling persona

• “He’d bet on who drinks water faster. Jordan is a betting monster.”
• “Craziest night. That’s not even the word.”
• “If I win, someone’s getting super blessed.”

These quotes don’t just entertain — they build the image of a man who lives and breathes risk, and knows how to make it pay.

Final thoughts: When gambling meets showbiz

Drake’s stories aren’t just anecdotes — they’re part of a bigger picture. In today’s landscape, gambling is intertwined with pop culture. Michael Jordan, Drake, Stake, the Super Bowl, Taylor Swift — all these names blur the line between entertainment and high-stakes betting.

Whether or not the $40 million win is 100% accurate is beside the point. What matters is this: Drake knows how to bet on himself, and so far, it’s working.

Source: msn