Drake Has Reportedly Bet $1 Billion Offshore Recently As Ontario Regulated Market Nears

Written By Martin Derbyshire on March 9, 2022 - Last Updated on March 16, 2022
Drake Stake Top 5 Betting Moments

Between all the Super Bowl bets, UFC wagers and roulette everywhere, Toronto hip hop king Drake is the unwitting poster boy for Canadian betting.

At a crucial time for gambling in Canada, as the new competitive market for sports betting and online casinos in Ontario launches on April 4, Drake has reportedly gambled $1 billion since December.

(Of course, it’s worth noting that when you’re continuously playing low-margin table games like blackjack or Drake’s favourite game roulette, betting handle adds up rather quickly. But still.)

Unfortunately, as Ontario enters a new regulated era, its most famous son is headed in another direction. Drake had become the de-facto spokesperson for the unregulated offshore Bitcoin casino and sportsbook site Stake.

However, that Drake-Stake partnership has now become official. On March 1, Drake announced through a video trailer on Instagram that he’ll be participating in some kind of live streaming gambling event on Stake.

The post’s caption reads:

“It was inevitable 🤑🤑🤑 Drake and @stake have come together 🤞🏽 I am going to be announcing a date for an upcoming live event where I play to win some real money and give it all to you because what’s better than sharing the love with my people 💴 stay tuned for details.”

For a guy who has done so much good for Ontario, you wonder if the rapper would consider a switchover to the legal, regulated market. Of course, that would entail a regulated operator willing to handle such large bets.

It also might require a nice, lucrative brand ambassador deal as well.

Overcooked Stake

Of course, Stake is an offshore sportsbook licensed in Curaçao, not Ontario. And, it doesn’t appear it will be part of Ontario’s regulated sports betting landscape since it’s a Bitcoin-free space, according to the Alcohol and Gaming Commission of Ontario.

That means most of Drake’s recent bets are not regulated, legal bets here in Ontario, and they never will be.

Right now, the Ontario Lottery and Gaming Corporation’s Proline Plus Sportsbook is the only legal online bookmaker in the province. Plus, OLG.ca is the only legal and licensed online casino. The rest of the province’s private market of online gambling sites doesn’t launch until April 4 (check out our live launch countdown here).

Still, all Drizzy’s grey market action begs for some kind of reaction.

So, we put together the following list of Drake’s top five most exciting gambling exploits leading up to the Drake-Stake partnership becoming official:

5. Action on and off the court

Drake is more than just the most famous Toronto Raptors fan on the planet and a courtside staple at Scotiabank Arena. Drizzy has been the Raptors’ official Global Ambassador since 2013.

What that means: Just like other NBA team employees, players or associates, Drake can’t legally bet on Raptors games. But it doesn’t mean he can’t bet at Raptors games.

That’s exactly what Drizzy was doing during an early 2022 Raptors home game at Scotiabank Centre. Attendance was limited to just 500 fans due to COVID-19 protocols in Toronto, so he explored the space.

As you can see from the screenshot of his Instagram below, Drake got in some live dealer roulette action on his laptop while the action was underway on the court.

He even joked that he “may as well,” since the extra room in the 19,800-seat arena provided by the capacity limits gave him an extra seat for his computer.

Drake Courtside Online Roulette Toronto Raptors
Screenshot from Instagram

Since Drake was clearly in Ontario when he played offshore roulette, it’s a move that could someday gain attention from authorities. However, regulators have not yet addressed how grey markets will be handled after the larger regulated market is launched.

4. Weeknd action at ARIA

Like Drake, Pepsi Super Bowl LV Halftime Show performer The Weeknd is from Toronto. So, it was no surprise to see Drake’s Insta poppin’ with pics from The Weeknd’s birthday bash in Las Vegas last month.

The surprise was how Drizzy spread around what looked like close to $200,000 at the ARIA Las Vegas high roller roulette table reserved just for him.

Covering that much of the board with that much money isn’t exactly the optimal play.

Should the Instagram photo be correct, No. 11 came in, and Drake may have had $20,000 on it, making him a cool half-million-dollar profit on that big spin. However, if this is Drizzy’s long-term roulette strategy, it’s a losing one and he might want to consider implementing some kind of roulette betting system or other plan.

Betting that much isn’t exactly responsible gambling, which espouses never betting more than you can afford to lose. That said, if you’re net worth is $200 million or more like Drake, perhaps a $200,000 bet is affordable.

3. Album-selling action in the octagon

There was a video going around on fight night showing Drizzy dropping $275,000 on Jorge Masvidal against Colby Covington in the UFC 272 headliner on Saturday.

The fight went the distance, Covington won unanimously, and Drake lost the bet. But what made this all noteworthy was the fact Covington addressed Drake and his bet in his post-fight press conference. The winning fighter flat out said:

“Let’s talk about all the money that Drake lost tonight. He needs to go back to selling those sh*tty albums to make back the money.”

By the way, Drake’s most recent “sh*tty” album, Certified Lover Boy, sold 613,000 units in its first week out. The total streams were second only to his record for Scorpion in 2018.

Meanwhile, Covington entered the weekend bout having made about $2.4 million in his UFC career, according to Sportskeeda. Each fighter reportedly made $532,000 for the fight Saturday, according to Sporting News.

(By the way, Covington has his own endorsement deal with an offshore sportsbook.)

Apparently, Drake has sold a total of more than 170 million “sh*tty” albums worldwide throughout his career, making him one of the top-selling artists in history. We should all be so “sh*tty.”

2. Super big bets on the Super Bowl

The Super Bowl is the biggest sporting event and biggest betting event annually.

It’s so big the American Gaming Association estimated a record 31.4 million people in the US would bet about $7.61 billion on Super Bowl LVI this year.

In the past, the Canadian Gaming Association has suggested more than $150 million in illegal bets are placed on the big game annually.

Numbers like that make it less shocking that Drizzy fired off $1.6 million in Super Bowl LVI bets last month. The shock was that he won all but one of the following three wagers on the Rams and his buddy Odell Beckham Jr.:

  • $600,000 on the Rams to win Super Bowl LVI (1.51 odds)
  • $500,000 on Odell Beckham Jr. to score a TD (2.15)
  • $500,000 on Odell Beckham Jr. to gain 62.5 receiving yards or more (1.81)

The receiving yards prop was the only loss. That means Drake got back all $1.6 million he wagered and earned $381,000 in profit. Regulation be damned.

1. A billion with a ‘B’

Hip-Hop insider news site Our Generation Music recently released a screenshot of Drizzy’s ‘DeepPockets6’ account info with the offshore Bitcoin casino and sportsbook site Stake.

They put it out on Instagram with a post that reads:

“#Drake has wagered over $1 Billion on Stake since joining in December 🤯👀”

The screenshot indicates DeepPockets6 started betting with Stake on Dec. 28, 2021 and has since placed 7,498 in bets worth some $1.531 billion in Canadian dollars or 28,459 of bitcoin.

The thing is, if all that the player loyalty and VIP programs at Stake offer billion-dollar bettors is some kind of live-streaming gambling event where they give away the real money winnings, Drake might want to consider taking his action elsewhere.

There’s undoubtedly much more to the Drake-Stake official partnership than has been publicly released. However, many privately-run online gambling sites set to launch in Ontario on April 4 have deep pockets too. They would pay handsomely to get Drake on board as some kind of Ambassador of Quan.

Either that or they’d welcome his kind of billion-dollar action with a decent rakeback deal.

Working or betting with a legal, regulated Ontario online casino and sportsbook fits much better with Drake’s undying support of everything Toronto. Not to mention, it would make all of his action legal, regulated and above board.

Photo by Mark J. Terrill / Associated Press
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Martin Derbyshire

Martin Derbyshire has more than ten years of experience reporting on the poker, online gambling, and land-based casino industries for a variety of publications including Bluff Magazine, PokerNews, and PokerListings. He has traveled extensively, attending tournaments and interviewing major players in the gambling world.

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