In our contemporary all-sharing, cross-functional media society – social entities are no longer confined to a singular definition or profession. Wrestlers can become movie stars, businesspeople can become politicians, and musicians can make headlines by placing giant wagers through offshore sportsbooks on major sporting events.
Did drake loose millions?
Canadian rapper Drake is just as famous for his music career as he is for his extravagant sports betting ventures. He frequently shares his betting activity and picks on social media, often baffling the online gambling community. While he wins a few, he’s sometimes seen as a curse, given he endured a barren spell of selecting teams who’d go on to lose.
He already stated in 2025 that he bet on the Baltimore Ravens in their playoff game against the Pittsburgh Steelers – a bet that paid off. However, he wasn’t as lucky at the end of last year when he bet over $350,000 on Mike Tyson to defeat Jake Paul…
Drake makes a lot of bets – but seemingly likes to bet on MMA the most, having spent over $12.7m on UFC fights over 23 bets.
Rubi Rose selected the Kansas City Chiefs.
Rubi Rose isn’t just a rapper. She’s an NFL fan and avid sports bettor and has had decent success with her selections. She was bold enough to place $1m on the Kansas City Chiefs ahead of the 2024 Super Bowl. She explained her rationale on her Instagram and some other markets she opted into: Marquez Valdes-Scantling would get at least 19.5 receiving yards in the big game.
French Montana backed Tom Brady.
French Montana has had a long career in hip-hop. In an authentic culture fit to the genre, he likes to splash the cash and wear lots of gold jewellery. Is there a better way to make money for said apparel than winning sports bets? Montana states that he believed the Tampa Bay Buccaneers and Tom Brady would win the 2021 Super Bowl.
The rapper has been known to gamble with some of his peers, commonly alongside Drake. The two often take opposing views on sports fixture results – and subsequently bet against one another for the spoils. 2016 Montana pocketed $60,000 from Drake after correctly predicting an NBA result.
Did Lil Tjay get into trouble?
Lil Tjay has been in the news for the wrong reasons lately. He’s been telling the press that he has a gambling addiction after a series of bets which have gone awry. He’s also said that one of the sportsbooks he plays with owes him a substantial amount of money.
Much like Drake, Lil Tjay was vocal in his support of Mike Tyson in the fight against Jake Paul. We all know how well that turned out.
50 Cent likes the in-play markets
Curtis James Jackson, better known as 50 Cent, is well known to like sports betting. He likes it at the moment instead of a premeditated wager. In 2012, he put down half a million dollars on the NFC Championship game.
That wasn’t the end of that betting journey, though…50 Cent put down his winnings from the prior bet that the Giants would win the Super Bowl. He would end up with a fortune as the New York franchise went all the way to win the Lombardi trophy.
He also left it late before putting a $1.6m wager on Floyd Mayweather to defeat Manny Pacquiao in their blockbuster fight 2015. This isn’t the only time that 50 Cent has been embroiled in boxing betting, having worked with Yuriokis Gamboa in a professional capacity. Rumour has it that 50 had a friendly wager with another rapper who would win in Gamboa’s fight with Terence Crawford.
Post Malone loves the NFL and Hard Rock Bet.
Heavily tattooed rapper and singer Post Malone has shown a very active interest in the FL, sharing his betting activity. With his popularity, Malone has partnered with Hard Rock Bet to become a brand ambassador. He is frequently seen on their socials talking about his top picks in the NFL game slates.
Young Thug won big in the Super Bowl.
Another rapper who enjoys profiting from NFL results is Young Thug. He has told the media that he won a massive wager of over $600,000 when he correctly predicted the 2020 Super Bowl result. However, Young Thug is often seen in casinos, especially in Las Vegas, where he is known to have a relatively poor record.