Drake is known for not being afraid to take a risk, but his latest gamble didn’t pay off, causing the rapper to lose close to half a million.

According to CBS, Drake bet $400,000 that Jake Paul would take out Tommy Fury during their Sunday fight in Saudi Arabia. However, the YouTube sensation didn’t come out on the successful side, making it Jake’s first loss in his career as a professional fighter.

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Drake was on track to gain $1.4 million if Jake would’ve won, but the rapper ended up losing his wager entirely. However, this is unlikely to be the last time Tommy and Jake fight it out in the ring. The duo have a rematch clause in their contract, in the event that Tommy won.

Even after the fight, Jake was already thinking about the re-match, and even made a promise to Drake about winning next time.

"$400,000 is nothing to him, he's won a lot more betting on me before so he's probably about even now," Jake said. "Sorry Drake, I'm gonna get that W in the rematch."

This isn’t the first time Drake has lost big thanks to gambling. In December, he was out $1 million after betting that Argentina would win the World Cup in the first 90 minutes. Though Argentina did beat France, they did so in half-time, making Drake’s prediction incorrect and causing him to lose the wager.

The month prior, Drake had a $2 million loss after wagering that UFC star Israel Adesanya would win in his match against Alex Pereira, which didn’t happen.

However, the “Passion Fruit” singer isn’t always wrong when it comes to betting. Drake has made some significant profits thanks to his bets in the past.

In July, Drake put down $2.2 million to bet that Molly McCann would beat Hannah Goldy and that Paddy Pimblett would win against Jordan Leavitt, both of which were right. The rapper walked away with $3.7 million.

After his winnings, Drake promised to buy the UFC fighters Rolex watches, though it’s unconfirmed if he went through with it.

Drake may have been hoping to put a dent in his legal fees with his latest gamble. Earlier this month, it was reported that Drake and 21 Savage settled a lawsuit filed by Vogue’s publisher Conde Nast. The duo had to pay an undisclosed settlement after using a fake Vogue cover to promote their album Her Loss last fall, despite not having the right permissions to do so.

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Sources: CBS, TMZ,