Rap Roulette & Revenue: Drake’s Gambling Legacy Across Both Industries

Although Drake excels in the music industry with thirteen No.1 hits on the Billboard Hot 100 and most top 10 singles (78), his performance as a high-stakes gambler is less impressive. 

Drizzy has been undertaking significant financial risks in recent years since his affiliation with Stake.com, an online casino and sports betting enterprise he partnered with in December 2021. Since then, he has allegedly staked over a billion bitcoins on the platform and squandered a substantial sum of actual money on sporting events. 

Whether it’s rap, roulette, or revenue, Drake is leaving a legacy across all industries due to the eye-watering money he earns and spends. But win or lose, it would seem the Canadian rap legend has an endless pot of money, and a few million lost or gained, to him, is a minorrrrr.

Drakes Rise to Superstardom & Net Worth

Drake, a prominent player in the music industry, has had a remarkable career since his debut in 2001. Originally known for his role in the Canadian television series Degrassi: The Next Generation, Drake turned to music in 2006 and rapidly attained widespread fame.

His inaugural album “Thank Me Later,” launched in 2010, ascended to the pinnacle of the charts, and he has sustained his preeminence thereafter.

Drake’s net worth is estimated at $250 million, demonstrating his substantial accomplishments in several domains, including music, acting, and business.

Drake has amassed almost $500 million over his career, underscoring his status as one of the highest-paid performers worldwide, although his yearly income has fluctuated considerably.

From June 2017 to June 2018, he accrued $45 million, while his profits for the year 2017 amounted to $95 million. In the subsequent year, he generated $75 million; from June 2018 to June 2019, he accrued $50 million.

Drake generates roughly $30 million annually, primarily from his music, touring, and other commercial endeavours. Then, a substantial increase in his net worth resulted from his 2022 agreement with Universal Music Group. This “long-term global partnership” includes recorded music, music publishing, film, television, and brand partnerships. Reports indicate that this agreement may have encompassed a $400 million first payment, substantially improving his financial position.

Drake the Entrepreneur

Drake’s income is not only derived from his music and contractual agreements. He has expanded his revenue sources through endorsements with prominent businesses such as Sprite, Nike, Apple, Burger King, and many more.

His enterprises, including the OVO Sound record label and the Virginia Black whisky brand, augment his riches.

Furthermore, Drake’s real estate assets are significant. He has many high-value homes, including his previous YOLO Estate in Hidden Hills, California, and an expansive estate in Toronto. In 2022, he acquired a house in Beverly Hills for $75 million and subsequently listed it for $88 million in 2023 and 2024.

One of the primary and most spotlight-driven out-of-music endeavours Drake has been involved with in recent years doesn’t stem from any of those mentioned above. He loves to gamble, and whether it’s roulette or sports betting, you won’t find Aubrey far from a sports betting app or online casino. 

Drake’s Love for Roulette

During a 2022 Livestream interview with Stake, Drake identified roulette as his preferred game when using the best legal online casinos and remarked that his passion for gambling emerged recently:

“I wasn’t gambling five years ago,” Drake commented. “I wasn’t really into it. I started in Vegas. I had a residency at one point in Vegas, and I would perform at this hotel, and that kinda got me into it. I started to attach emotion to it, which people say don’t do, but I used to live by the mantra, ‘It’s business, not personal,’ but it’s personal and not business. Gambling is another thing I make personal. I bet my mom’s birthday. I bet my brother’s and kid’s birthday. I bet my birthday… and I just ride it out.”  

His most significant achievements occurred during live-streamed events in collaboration with Stake. Indeed, in May 2022, one play on a live roulette table resulted in a victory of over $17 million. 

In the same month, he incurred losses of over $660,000 from betting on Formula 1 and UFC. Aside from an eight-figure gambling loss (about $25 million alongside French Montana), all of Drake’s significant losses since January 2022 have been from his diverse sports bets.

Notwithstanding his setbacks, the Toronto native accumulated over $79.1 million in winnings since affiliating with Stake.com.

Stake.Com Partnership & ‘The Drake Curse’ 

The success of Stake Casino may be ascribed to its intuitive design, extensive game variety, and commitment to equitable gaming practices. The casino functions under a Curacao eGaming license, providing regulatory supervision and safeguarding for players.

Nonetheless, this crypto casino’s ascent to prominence in the online gaming sector was hastened by its unforeseen partnership with Drake, the renowned Canadian artist and entrepreneur. Drake’s association with the online casino was pivotal for the company, immediately enhancing its legitimacy and appeal.

The agreement significantly enhanced the visibility of the Bitcoin casino. Drake’s extensive social media presence and fan base ensured his sponsorship impacted millions globally. His tweets and references to Stake Casino on sites such as Instagram and Twitter elicited significant attention, resulting in a substantial influx of new users.

In step, ‘The Drake Curse.’ 

He isn’t just a partner but an avid bettor. However, Drake’s poor history with sports betting has led many to believe in the “Drake Curse,” which posits that any athlete backed or gambled on by him experiences a loss…When you look closely at his track record, it’s easy to see why. 

Since 2022, let’s take a look at Drake’s largest staked bets and the reason why ‘The Drake Curse’ continues: 

• Soccer – Canada to defeat Argentina – Lost $300,000 (2024) 

• UFC- Pereira to defeat Hill – Lost $425,000 (2024) 

• Boxing – Fury to defeat Usyk – Lost $565,000 (2024) 

• NBA – Mavericks to defeat Celtics – Lost $350,000 (2024) 

• NFL – Chiefs to Win Super Bowl – Won $1.2 million (2024) 

• UFC – Strickland to defeat Du Plessis – Lost $700,000 (2024) 

• UFC – Adesanya to defeat Strickland – Lost $500,000 million (2023) 

• Boxing – Jake Paul to defeat Tommy Fury – Lost $1.2 million (2023) 

• NFL – Chiefs Win Super Bowl – Won $500,000 (2023) 

• Soccer – Argentina to defeat France in World Cup – Lost $1 million (2022) 

• F1 – Leclerc Wins Spanish GP – Lost $230,000 (2022) 

• Soccer – Barcelona to defeat Real Madrid – Lost $600,000 (2022) 
• NFL – Rams to Win Super Bowl – Won $300,000 (2022) 

• UFC – Masvidal to defeat Covington – Lost $275,000 (2022) 

Final Thoughts 

As evidenced above, Drake’s luck on sports wagering hasn’t been as fruitful as his roulette endeavors. Still, either way, it’s imperative to avoid following the gambling pursuits of a multi-millionaire who lives a very comfortable lifestyle. The stakes that we witness Drake lay down aren’t that high when compared to his net worth, and as one of the biggest names in the rap industry, he can earn any losses back rapidly. 

Drake clearly loves to gamble, but he also bets on himself. Regarding sports teams and Kendrick Lamar, however, perhaps the Canadian rap mogul should sometimes think twice before allowing himself to take the gamble.