Drake Loses $250k Betting an Underdog NCAA Tournament Final Four Parlay

World-renowned megastar, recording artist, and high-roller Drake placed an ill-advised $250k parlay on the NCAA Tournament over the weekend.

Drake rolled into the Final Four backing a pair of underdogs, No. 9 Florida Atlantic and No. 5 Miami, in their matchups against No. 5 San Diego State University and No. 4 UConn. Whereas the Drake curse used to apply to teams he publicly supported, it now seems to harm teams he bets on as both went on to lose.

The bet would have paid just under $1.6 million if it cashed, but it ultimately did not. Nobody ever accused the “Her Loss” hitmaker of being the best on the books, even if he is a beast on the boards.

Drake’s wager came with good intentions. America had fully bought into the Cinderella story that was FAU, a team that had only made March Madness one time before this year and had never won a game.

Despite being the nine seed, the Owls went 28-3 in the regular season—tied for the second-best mark—and turned in plenty of great performances in the bracket, even if they needed a game-winning layup with two seconds remaining to sneak past No. 8 Memphis in the opening round.

FAU entered the game against San Diego State, the eventual national runner-up, as a two-point underdog. They led by as many as 14 points with just about 14 minutes left in the game but fell victim to a late comeback, which they had grown accustomed to pulling on their opponents, not the reverse. The game ended 72-71 on a buzzer-beating game-winning pull-up jumper from Lamont Butler and sent the Aztecs to their first national title game in program history.

Funnily enough, Drake’s bet would have still been alive had he taken the Owls on the spread, as small as it was. But the same cannot be said for the Miami-UConn game, which was as dominant a 13-point win as there has been in college basketball all year. The Huskies swarmed the Hurricanes on defense all night and executed their offense to perfection, and even opened a lead as large as 20 points.

UConn easily covered the 5.5-point spread with the 13-point win, which was ironically its smallest margin of victory in the entire tournament. They ended up beating SDSU in the national championship 76-59 and became the first team in NCAA Tournament history to win every game by a minimum of 13 points.

Drake is no stranger to pushing online sportsbooks to their limits but does not have the best track record of winning them.

The Canadian-born singer/rapper got into high-stakes gambling publicly with the help of Stake, a crypto-based gambling platform that soon signed a partnership agreement with their celebrity patron. Drake went on to host gambling streams on Twitch, during which he would play his favorite casino games and give away prizes.

Drake has also placed losing bets on seemingly every sport and league, including the NFL, F1, UFC, and more.

Amazingly, Drake even lost a $1 million bet that he won (kind of). He correctly picked Argentina to win the 2022 Qatar World Cup over France but said that they would do so in 90 minutes, which is where he went wrong. The game was tied 2-2 after the 90 and 3-3 after 120 and needed to be decided by penalty kicks.

Drake’s UFC losses have been especially brutal. In 2022 alone he lost a combined $2.6 million unsuccessfully wagering on the outcomes of various fights.

His big win, however, came in the AFC Championship Game between the Kansas City Chiefs and Cincinnati Bengals. That netted him over $2 million and set him up for a successful Super Bowl, on which he placed a litany of bets—many of them did not hit, but he got the eventual winner, the Chiefs, nailed on.

Drake can be criticized for a variety of reasons, but he can never be faulted for not being upfront. He regularly posts his betting slips to remain transparent with his audience—and to occasionally gloat when they cash.