While Drake is a dominant force in music, his track record as a high-stakes gambler isn’t as stellar. Drizzy has been taking insane risks with his money these past few years ever since joining Stake, an online casino and sports betting company, in December of 2021. Since then, he’s reportedly wagered over a billion in cryptocurrency through the platform and gambled away a fortune of real money on sporting events as well.
In a livestream interview with Stake in 2022, Drake cited roulette as his favorite game and said his love of gambling developed relatively recently.
“I wasn’t really gambling like that five years ago,” Drake said. “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 definitely personal and not business. Gambling is another thing I make it personal. I bet my mom’s birthday. I bet my brother’s, kid’s birthday. I bet my birthday…and I just ride it out.”
Drake has previously thanked his gambling alter ego Anita Max Wynn for his big wins, which included over $1 million on the 2024 Super Bowl, and another $1 million on a boxing match last year. However, while not every bet Drake has made has been documented, The Boy has suffered a significant number of losses over the years. While not all his bets have been publicly documented, Drizzy has lost an estimated $7 million at this point. His losing streak is so great that the sporting community refers to Drizzy’s gambling as the “Drake Curse.” The curse is that whatever team Drake bets on will likely suffer a stunning defeat.
Judging from his wins and losses below, the “Drake Curse” does seem to be alive and well. Here are 16 of Drake’s biggest gambling moments from over the years.
