Still on Top of Spotify – But Is Drake Gambling His Future on Casinos?

While his name still sits atop Spotify’s global charts, pulling in millions of streams daily, a much bigger question is quietly spreading across the music, finance, and even online gambling communities: Is Drake – the music icon of a generation – secretly gambling his artistic future on the casino industry?

Drake, born Aubrey Graham, has long been more than just a rapper. He’s a global brand — from his Virginia Black whiskey, to his OVO fashion line, to massive international campaigns with Nike and Apple. But his highly controversial partnership with Stake.com — a crypto-based online casino platform that has faced regulatory scrutiny in multiple countries — is triggering waves of speculation. Why would an artist still dominating the charts dive so deeply into one of the world’s most controversial industries?

Drake – Hip-Hop’s New “Casino Boy”?

According to a report by Rolling Stone and confirmed by Billboard Canada, Drake signed a multi-million dollar deal with Stake.com back in 2022. Since then, he has consistently livestreamed high-stakes gambling sessions on Twitch, sometimes placing bets of up to $1 million on roulette, poker, and even sports betting — notably, on NBA games involving the Toronto Raptors, the hometown team for which he serves as a global ambassador.

“I do it for the thrill, not the money,” Drake said during a March 2023 live broadcast, where he reportedly won over $3 million in just 15 minutes, only to lose $2 million a few days later.

However, music industry analysts aren’t convinced this is all just for fun. Many are beginning to question whether Drake is shifting his financial focus — from streaming music to streaming gambling — as a way to offset declining music revenues.

Streaming: Still Strong, But No Longer “Untouchable”?

Although tracks like “First Person Shooter,” “Rich Baby Daddy,” and most recently “The Heart Pt. 6” continue to dominate Spotify’s top charts, data from Chartmetric and Music Business Worldwide reveals a slight decline in Drake’s average streaming numbers compared to his peak years from 2018 to 2021.

In 2021, Drake had as many as 9 songs simultaneously on the Billboard Hot 100. By 2024, that number had dropped to just 3.

No one is calling Drake “washed up,” but it’s clear the musical landscape is evolving — the surging popularity of artists like Kendrick Lamar, Lil Baby, Travis Scott, and rising Gen Z names such as Ice Spice and Sexyy Red is putting pressure on the 2010s golden generation to reinvent themselves.

Casino – Lifeline or Firestarter?

Drake’s involvement with Stake.com goes far beyond simple sponsorship. He livestreams weekly, engages directly with fans, and has branded campaigns like #DrakeStakes and #BetWithDrake. On X (formerly Twitter), a video of Drake betting over $500,000 on a UFC match garnered more than 90 million views within 48 hours.

Stake even launched a dedicated section called “Drake’s Picks” on its website — allowing users to copy his exact bets in real-time.

“I’ve never seen an artist so actively pull fans into the world of gambling,” said Charlie Hanson, a financial analyst at CNBC Music Biz.

Hidden Consequences: From Ethics to Legal Risks

Stake.com is registered in Curaçao, a known tax haven. While legal in certain jurisdictions, the platform has come under investigation in Australia and the United Kingdom, and is even banned in several U.S. states, including New York, Washington, and Michigan.

Public criticism has mounted — especially given that a large portion of Drake’s fanbase consists of teenagers and young adults. A viral Reddit campaign once trended under the hashtag #StopStakeWithDrake, urging the rapper to cut ties with the platform. “He’s teaching an entire generation that gambling is cool,” one user wrote. “No one talks about what happens when you lose everything.” And the backlash isn’t just ethical — it may soon be legal. According to lawyers in Toronto, where Drake’s business is headquartered, he could face legal consequences if found promoting online casinos in regions where gambling is not licensed or regulated.

The OVO Empire – Is It Changing Direction?

Since partnering with Stake.com, the financial engine behind OVO — Drake’s globally recognized streetwear label — has started to show signs of a clear and deliberate shift. No longer just a fashion brand built on exclusivity, music influence, and Toronto pride, OVO is now increasingly tied to the world of gambling aesthetics and gamified marketing strategies.

Recent OVO collections have leaned heavily into casino-inspired visuals: graphic prints of playing cards, roulette wheels, and poker chips now adorn premium hoodies, snapbacks, bomber jackets, and even limited-edition accessories. The line, once defined by minimalist owl logos and muted luxury, now pulses with the energy of the casino floor — loud, flashy, and risk-driven. But this isn’t just about design.

In 2025, OVO stepped further into the gambling world by becoming the official sponsor of a series of international poker tournaments held in Macau and Las Vegas — two of the world’s most high-profile gambling capitals. These weren’t side ventures; they were branded events, with Drake’s OVO owl logo splashed across tournament banners, live streams, and every single gaming table, turning the brand into a visible force within the professional poker scene.

In a now-viral Instagram Story posted in April, Drake shared his vision bluntly: “I’m not just playing — I’m building a culture.”

To some, it’s a bold evolution of brand identity — transforming OVO from just a music-meets-fashion label into a full-blown entertainment empire with fingers in multiple industries: music, fashion, sports betting, and now, high-stakes poker. To others, it’s a risky rebranding — one that blurs the line between lifestyle and vice marketing, particularly when considering OVO’s younger demographic.

Whether this move proves visionary or volatile, one thing is clear: Drake isn’t just wearing the casino — he’s monetizing it. And in doing so, he’s taking OVO into uncharted territory.

Long-Term Strategy or a Dangerous Gamble?

When asked whether he had any intention of ending his public gambling activities, Drake offered a brief but telling response: “No. I’m winning.”

But the real question isn’t whether he’s winning now — it’s how long can he keep winning? And what happens if he loses — not just money, but credibility, cultural influence, and most importantly, the trust of his fans? At what point does this stop being a clever financial pivot and become a high-stakes risk to his artistic legacy? As Drake continues to merge his hip-hop empire with the world of online casinos, some are starting to wonder if he truly understands the game he’s playing — because he’s not just betting money anymore. He’s betting his legacy.