Drake’s Biggest Roulette Wins and Losses

Chips Falling on Roulette WheelWith a net worth of an estimated $250 million (£210 million), it’s fair to say that rap artist Drake has plenty of spare change with which to enjoy his hobbies.

It’s pretty evident that one of his favourite pastimes is gambling, with his wins and losses at the casino and in sports betting fast becoming the thing of legend.

Like most casino gamers, Drake’s results are very much of the ‘you win some, you lose some’ realm, it’s just that the amounts of cash he is splashing out are such that they make the average Joe and Jane wince.

But in his role as brand ambassador for the crypto casino Stake.com, is all as it appears to be?

Spinning the Wheel

3D Red Casino Chip

“Drake is a celebrity whale. He’s one of the most in-demand gamblers by casino marketing departments. I saw him at Aria, and he was betting $200,000 a spin at roulette.”

Those are the words of professional sports gambler Bill Krackomberger, and he is just one of many people that have observed the rapper going about his business in casinos across North America.

Some of those stories have entered folklore. The multiple-time Grammy Award winner was on tour back in 2018, and after playing a gig at the Wells Fargo Center in Philadelphia, enjoyed an after-party that saw the rapper and his entourage head to the Hard Rock Casino in Atlantic City.

In a portent of what would follow over the next few years, Drake ended up shelling $200,000 in losses on the private tables – although it should be said he commanded a fee of around $300,000 for playing a 3am show at the Daer Nightclub on site at the casino.

And then there was the time that the 35-year-old took his seat courtside at a Toronto Raptors game – the rapper is a huge fan of the NBA outfit. Needing some half-time entertainment, Drake whipped out his laptop….and proceeded to play online roulette while he waited for the action to resume.

But it’s Drake’s partnership with the crypto casino outfit Stake.com that has attracted the biggest of his splurges. It has been suggested that he has invested in the firm and become a brand ambassador, sharing several posts on his social media channels with the Stake branding on them.

As part of the deal, the Drake x Stake live streaming series was born. Here, the Canadian plays roulette and other games on the platform in real time, celebrating his wins, commiserating his losses and even sharing his spoils with the viewers.

Some monumental sums have exchanged hands. Between December 2021 and February of this year, it has been estimated conservatively that Drake has wagered more than $1 billion.

Casinos have been hit by closures and reduced operating hours, so Drake has made the move online – earlier this year, in an orgy of online roulette, he won a reported $18 million with a single chip on number 11….before losing it all, and then some, in losses tallying a knee-trembling $20 million.

Another live stream on Twitch saw Drake inflate his bankroll to more than $27 million, but by the end he had just $1,879 in his account – not aided by the humongous amounts he stakes per spin:

It’s known that Drake plays a lot at from his Toronto mansion too even when the cameras aren’t rolling – he shared one win of $7 million in a video on his Instagram feed, yelling ‘there it is! What did I say? What did I say?!’ when his punt on number eight came up trumps.

So legendary is Drake’s love of gambling he has even gone to the extreme of foregoing being able to tell the time, instead wearing a roulette watch designed by the Jacob & Co company. The $620,000 piece has replaced the traditional clock face with a roulette wheel – Drake and former UFC star Conor McGregor are thought to be two of just a handful of people on the planet to own the watch.

Skin In the Game

American Football with Piles on Money

When he isn’t trying his luck in the casino, Drake can often be found cheering on his sports bets.

The rapper has dropped hundreds of millions on dollars on various wagers over the years….with mixed results.

In one single night, on February 13, 2022, Drake wagered a total of more than $1 million on three different Super Bowl LVI bets.

He splurged $471,000 on the Los Angeles Rams to win – which they did, courtesy of a last minute touchdown, and he also wagered $393,000 on his friend, the Rams’ Odell Beckham Jr, to score a touchdown of his own….he duly obliged.

Drake had backed Beckham Jr to record more than 62.5 yards with ball in hand – sadly that bet lost when the wide receiver suffered a game-ending knee injury, but nonetheless the rap ace still found himself around $166,000 to the good from his trio of wagers….not bad for a day’s work.

The 35-year-old is also known to be a fan of UFC, and that organisation’s fights have represented some of Drake’s best and worst results in sports betting. Wins for Israel Adesanya, Paddy Pimblett and Molly McCann have net him $3.3 million in profit, although that has been counteracted by costly defeats for Justin Gaethje ($550,000) and Jorge Masvidal ($275,000).

Drake has dipped his toe in the water of other sports, and banked $1.8 million when the Golden State Warriors won both the Western Conference and the NBA Finals during the 2021/22 season. However, a parlay involving the Brooklyn Nets, Dallas Mavericks and Toronto Blue Jays saw him hand back around $300,000.

And he’s not afraid to bet against his friends in his pursuit of a win. Earlier this year he wagered against his good buddy Lewis Hamilton by wagering on Ferrari’s Charles Leclerc to win the Spanish Grand Prix. Alas Max Verstappen romped home in first place for Red Bull, and Drake found himself $250,000 out of pocket.

Drake x Stake: Is It Legit?

When you dig a bit deeper and think about this partnership in more detail, the more it begins to seem a little untoward and sketchy.

Both Drake and Stake.com have been open publicly about their hook-up, and it goes without saying that the casino operator benefits greatly from the relationship – Drake, after all, has more than 100 million followers on social media, and must drive untold numbers to the live stream videos he puts out on behalf of the firm.

The question now is how much does Stake pay Drake for the privilege….and are they putting up the money that he bets in the live streams?

Let’s think about it: in one of the Drake x Stake videos, he loses $20 million. That’s 8% of his entire estimated net wealth….would anyone seriously risk losing that much on a few spins of a roulette wheel?

It’s interesting again to note how much money (or crypto, in this case) Drake has given away to the live stream viewers. On occasions he has forked out a total of $1 million to lucky viewers, handing out packages of 2.6 BTC – around £45,000 – to those fortunate to be picked.

With PR like that, how can Stake.com fail in their bid to drive more traffic and depositors to the brand!?

Another question mark is how Drake is able to wager so much on each roulette spin. There is no way that Stake would allow the average layman a chance to wager $200,000 or more per turn – indeed, their stated maximum stake is actually $20,000, and you wonder what the responsible gambling team of the Ontario regulator are doing when the rapper advocates betting six figure sums to his millions of followers.

There’s plenty of smoke and mirrors going on here, and you wonder how long it will be before regulators clamp down on what is a wholly irresponsible partnership.