As the world's top tennis stars battle it out under the bright lights of New York, an unexpected spectator is making just as many headlines from the sidelines. Music superstar Drake, whose relationship with high-stakes gambling is as famous as his chart-topping hits, has once again placed a colossal bet, this time pinning his hopes and a cool $300,000 on Italian sensation Jannik Sinner to win the 2026 US Open. The rapper, known for his lavish lifestyle and equally lavish wagers, seems determined to use the tennis court as the stage to finally dispel the notorious 'Drake Curse' that has haunted his betting slips for years. Fans are watching with bated breath, wondering if Sinner's powerful backhand is strong enough to smash through a jinx that has felled champions before him.

The Notorious 'Drake Curse': A Woeful History

Let's rewind the tape on Drake's less-than-stellar sports betting portfolio. It's a saga filled with near-misses and spectacular misfires that have become legendary in their own right.

• The World Cup Heartbreak (2022): Drake confidently placed a $1 million bet on Argentina to defeat France within 90 minutes of the World Cup final. While Lionel Messi did eventually lift the trophy, he did so after a nerve-wracking penalty shootout. Drake's bet, requiring a regulation-time victory, vanished into thin air. 😬

• The UFC Upset: His misfortune continued in the octagon. A whopping $1.2 million was lost when MMA star Israel Adesanya, whom Drake had backed, was defeated by Alex Pereira at UFC 281.

• The Curse is Named: It was Adesanya's subsequent loss to Dricus du Plessis—after Drake posted about a $450,000 bet on him—that truly cemented the 'Drake Curse' in pop culture lore. The pattern was clear: an athlete receiving Drake's public betting endorsement seemed to be marked for defeat.

This history makes his current tennis venture all the more dramatic. Is he a gambler chasing redemption, or is he about to add another chapter to his curse's legacy?

All In on Sinner: Drake's Tennis Muse

For the 2026 US Open, Drake has gone for the top seed and reigning champion, Jannik Sinner. The Italian world number one has been in imperious form, blasting through the early rounds. Drake took to Instagram to share a screenshot of his bet: $300,000 riding on Sinner to win it all. A Sinner victory would not only net the rapper a profit of $207,000 (a total payout of $507,000) but, more importantly, it would deliver a decisive blow to the curse narrative.

Interestingly, this isn't Drake's first financial flirtation with the Italian star. Their betting relationship has seen a fascinating evolution:

As the table shows, Drake seems to have learned his lesson from 2024. Betting against Sinner didn't work out, so now he's firmly on the Sinner bandwagon, riding it all the way to (hopefully, for him) the bank.

The Road to Glory (and a Payout)

The path to cashing that $507,000 check is clear but fraught with danger. Sinner's immediate challenge is a quarter-final clash against his compatriot, Lorenzo Musetti. Should he navigate that, a semi-final against either Felix Auger-Aliassime or Alex de Minaur awaits—a match he would be heavily favored to win.

The real test, and the potential curse-breaking moment, would likely come in the final. Waiting there would almost certainly be one of the two other titans of the game: the ageless wonder Novak Djokovic or the explosive Carlos Alcaraz. A victory over either in a Grand Slam final is the ultimate credential, and for Drake, it would be the ultimate vindication.

Will Jannik Sinner's powerful game and cool demeanor prove to be the kryptonite to the 'Drake Curse'? Or will the curse extend its reach to the tennis court, adding a world number one to its list of victims? One thing's for sure: the stakes at this US Open just got a lot higher, and not all of them are measured in ranking points. 🎾💰