Does Drake Have a Gambling Problem? It’s Somehow Even More Depressing Than That

You’ve heard of the Trump curse, but what of the Drake curse? The rapper and loser in the great beef of 2024 has a habit of betting on the wrong horse. He loves to show off his big-stakes gambling slips on social media, showing just how often he fails with his picks. He bet $1 million that sex criminal Conor McGregor would win in his UFC comeback fight (he lost in 69 seconds). He picked Argentina to win the World Cup and they lost 1-0 to Spain. There’s an entire website dedicated to tracking Drake’s bets and their outcomes: TheDrakeCurse.com!

According to that site, Drake has made 88 public bets and won 32 of them. His status as a loser has become such a joke that people actively wager on whoever he bet against. But don’t cry for him. According to that site, his returns are pretty solid, if only because he makes such large wagers. What’s $1.5 million between friends? It’s all minor.

Gosh, I’d feel sorry for him if it were anyone else. It sure seems like he’s addicted to gambling, right? The idea of casually blowing seven figures on the result of an MMA fight is obscene enough, but wagering it on the out-of-shape abuser who can barely fight sleep must be the sign of a humiliation kink. Is it an addiction? Probably, but it’s also something way more toxic than that.

I’ve gone on the record more than once about my disdain for the endless gamification of everything and smothering takeover of the gambling market on our lives. The World Cup was an endless nightmare of gambling ads and implicit endorsement of addiction that left me feeling queasy. In only a few short years, America has become engulfed with the practice known euphemistically as gaming and its pervasiveness has irrevocably changed myriad aspects of both sports and fandom. Athletes are harassed by gamblers when bets don’t go their way. Gambling disorder cases spiked earlier this year in the USA, and in the UK, the NHS has reported a doubling in the number of gambling addicts needing treatment over the past year. One person reported becoming so addicted to the app FanDuel that it lost them millions. The company responded by having a baseball player, Bryce Harper, send him a personalised holiday message. And this doesn’t even get into the mess of prediction markets, which are somehow even more evil.

Part of the mainstreaming of gambling has occurred through the use of celebrity endorsements: Chris Rock, Kevin Hart, Mike Tyson, Cristiano Ronaldo, Jamie Foxx, Danny Dyer, Wayne Gretzky, and too many former athletes and managers to name. it’s largely men shilling it, often in a snappy suit and a glitzy casino, the likes of which only exist in Bond movies. They talk up not only the thrill of a bet but the idea of it as a community experience. Hey guys, you know that whole male loneliness epidemic that’s unfolding? Why don’t you fix it by wagering all of your savings on a college basketball game? Have a cheeky flutter and feel like a real man! It’s meant to be glamorous and, let’s be honest, gender affirming (women aren’t sold to as much in this field, but when we are, it’s usually with fluffy pink and bingo apps.)

Drake is a part of this system, because of course he is. Aubrey is an expert at snatching cringe from the jaws of dignity, and despite him being Not Like Us, he commands an intensely loyal fanbase and chart dominance through his achingly long albums. Indeed, he seems to have even more devoted fans since dropping that veil of self-aware self-loathing in favour of bitterness and misogyny. He’s a Free Tory Lanez creep, after all. Really, he’s kind of the perfect spokesperson for a seedy gambling organisation.

According to the Financial Times, Drake signed a $100 million a year endorsement deal with Stake, and he is promoting it hard. That company is banned in numerous countries. His social media presence feels more like a marketing campaign for gambling than a promotion of his music. As Pitchfork noted, Drake does a ton of Kick streams with Adin Ross, a man who was banned from Twitch for hateful content and who pals around with Andrew Tate (he also has a deal with Polymarket.) “They have the gall to offer motivational speeches in the middle and end, some virtuous window dressing to an otherwise unsavory two and a half hours of gambling,” wrote Kieran Press-Reynolds.

Drake and Ross, by the way, were accused in a US civil case of using online casino money to pay for automated streams in a bid to artificially inflate his royalties and online popularity. The lawsuit alleges Stake has paid Drake $100m a year and provided free gambling credit to both him and Ross.

These sleazeballs using a crooked company and a crooked streaming platform to line their pockets is, well, pretty unsurprising. I’m sure Drake would push any number of people in front of a moving truck if someone offered him a dollar. But I do think it’s worth noting how his meme status as a gambling loser is a barely veiled cloak for a giant ad campaign largely designed to appeal to his young male fanbase. “It’s like a hit,” Ross screamed during one stream as they lost more and more money. The chances are, however, that he’s not even betting his own money. Stake is most likely covering the costs because they see it as a worthwhile investment for all the new cash his name draws to their company. To once again quote Pitchfork, “Drake becoming Stake’s cultural mascot is insidious—he’s marketing the app to millions of aspirational obsessives, turning his fanbase into a horde of gambling degenerates who trust their favorite influencers’ baseless “calls” with divine faith. It’s astrology for boys nursed on Barstool. It’s even darker because Stake likely gives Drake credit to use for promotions, so there are no stakes to him going berserk with bets. He always wins.”

It’s just a slimier version of, say, Kevin Hart doing ads talking about how amazing online casinos are. They’re all rolling around in the same drain of greed and exploitation. In many ways, the desperation of Drake on a live stream with a right-wing loser playing children’s games for millions is more honest than a CGI version of Monte Carlo where all the hottest people hang out. Gambling bodies want less regulation, fewer restrictions, and more captive audiences from younger and vulnerable demographics. Why not have Drake be their pied piper? A desperately insecure man child whose money cannot make him happy or interesting is the ideal face of this scam.