Drake: Biggest Bets, Wins and Losses


The Come Up Show, CC BY 2.0, via Wikimedia Commons

He might be known as a superstar rapper to the average guy and girl on the street, but to those in the casino and betting industry, Drake is known as a celebrity whale.

He is arguably the most in demand high stakes celebrity gambler out there for bookmakers’ marketing departments, regularly losing crippling amounts of money and also making bets that don’t always hold much value.

For example, risking $1 million to win $220,000 isn’t exactly a genius move, even if the odds are very much in your favour.

It’s not just sports bets either; Drake loves the casino, regularly betting big on roulette, and in one particular case he lost $20 million playing the game via Twitch, a streaming service that lets fans watch people playing video and casino games.

It is thought that he has wagered over $1 billion through Stake, a platform he has a sponsorship deal with, but obviously that accounts for money bet rather than money lost, and some of his bets have been big winners as well as big losers.

He’s worth around $150 million, so although this is big money, it’s money he can ‘afford’ to spend, but still, it must be crushing when some of those big bets fall through.

Drake's Biggest Bets

$2 Million UFC Bet on Adesanya Costs Drake Big

Bet: $2,000,000 (£1,622,680) - Adesanya To Beat Pereira - Lost

You might think that betting on a man who had already lost twice to his next opponent would be foolish. Not Drake, though.

To be fair to him, Adesanya was the reigning UFC middleweight champion of 3 years, and had a good 5 years experience on his contender, Alex Pereira, in MMA.

Although Pereira had beaten Adesanya twice before, they were both kick boxing fights, so this was a different kettle of fish, but still, the risk to reward ratio was not worth the $2million Drake staked on the fight.

Finally a Win for Drake as Kansas Chiefs Net Him $2.1 Million

Bet: $1,129,638 (£916,147) - Kansas Chiefs To Beat Cincinnati Bengals - Won

This bet was on the Kansas City Chiefs to win the match including extra time, and although the majority of punters didn't agree with him, this time, Drake got it right.

A good job too since there was over $1.1 million dollars on the line and he was already $850,000 dollars down that day alone. This man certainly isn't scared of risk.

The game was incredibly important for the teams involved because the winner would progress to the Superbowl, but with all that money at stake you could argue that it was even more important to Drake.

Drake Bets $1 Million on Argentina to Win World Cup but STILL Loses

Bet: $1,000,000 (£811,380) - Argentina to Win the World Cup - Lost

A rookie error or simply just a bad decision? We may never know, but only Drake could lose $1 million on a game which he correctly predicted, by choosing the wrong bet.

It was the World Cup final in 2022, between Argentina and France, and Drake has a 1x2 on Argentina for the win.

Can you spot his mistake?

Drake Bags $1.38 Million When Gervonta Davis Beats Ryan Garcia

Bet: $1,000,000 (£802,810) - Gervonta Davis to Beat Ryan Garcia - Won

Drake managed to notch up another big win in April 2023 after a series of losers that led to him being known as cursed. That curse seems to have been lifted though, since his bet on Gervonta Davis to defeat Ryan Garcia came in when the two faced off in Las Vegas.

In true Drake fashion though, it wasn't the only bet he made that night, and several smaller more specific bets failed to land, but it didn't make much of a dent in his total return.

As always, the bet was made via Drake's favourite betting platform, Stake, with which he has a partnership of sorts, and where he regularly places large wagers and then advertises the fact on social media.

Kansas City Chiefs Win Big for Drake: Nets $1,477,000

Bet: $700,000 (£580,000) - Kansas City Chiefs to Win the Superbowl - Won

Having won big on the Kansas City Chiefs a month earlier, Drake went big on the team again backing them to win the Superbowl to the tune of $700,000.

It was to be another successful bet, but that doesn't quite tell the whole story, because it wasn't the only bet Drake made on the game.

It was the only one he won though.

Yet despite losing all of his other bets he still came out on top financially, but it was touch and go for a while.