Drake betting $300K against Messi—Gutsy move or just plain reckless?

Betting is an eventual part of sports, and soccer is no exception. Expert bookies and fans alike test their prediction skills, hoping to cash in significantly if their prophecies come true. Many celebrities also take a chance with destiny, and one of the most notable names in this arena is Drake. The American singer recently gambled $300K on Canada to win their Copa America 2024 semifinal clash against Lionel Messi‘s Argentina. However, his prediction did not pan out, resulting in a significant loss. This event instigates a closer look at Drake’s past betting record and how has he fared in other sports, such as the NBA Finals and the Super Bowl.

Other A-listers betting in sports has never been as controversial as Drake doing so. The American rapper has a unique history when it comes to gambling as many even call him a ‘curse.’ This is because whoever he places the bet on, losses. Today was no exception as CanMNT lost 2-0 to reigning champions, with Drake also losing out on a potential $2.8-million payout. So which other bets have seen him face major financial loss?

Bets that made Drake a ‘curse’ in the sporting world


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2016 NBA finals

via Imago

During the NBA finals between the Cleveland Cavaliers and the Golden State Warriors, Drake bet fellow rapper French Montana $60,000 that the State Warriors would win game seven. However, not only did he lose—courtesy of LeBron James turning up pretty well for the Cavaliers—but he also received a taunt from French Montana, saying, “Shout out to my brother Drake for that 60 bands because you didn’t believe in LeBron.” 

2024 NHL Stanley Cup

Just a few weeks ago, Drake placed a $500,000 bet on the Edmonton Oilers to win the Stanley Cup Final against the Florida Panthers. However, this time his prediction didn’t pan out, as the Oilers lost. If his prediction had been correct, he would have pocketed $1.025 million.

2024 NBA Finals

Drake wasn’t in the mood to give up as he placed a similar bet of $500,000 on the Dallas Mavericks to clinch a victory over the Boston Celtics. However, he again missed out on a whopping number of $1.375 million. 

However, not every time he has faced financial losses as a few bets have turned out quite well in his favor.

Sports bets that Drake has won and made him roll in the dough!

2022 Super Bowl LVI

This time instead of betting with someone else, he decided to place a $600,000 wager on a gambling site to predict that the Los Angeles Rams would win the Super Bowl. To his fortune, the Rams did win as Drake cashed out almost $906,000.

2022 FIFA World Cup final

via Getty

The year 2022 proved lucky for Drake as this time, he decided to place a whopping $1 million wager on Argentina to win the World Cup final against France. Everyone thought that it would be due to the 37-year-old that Lionel Messi wouldn’t be able to win his first-ever WC. Yet, he defied the odds as not only Argentina ended their 36-year exile, but Drake won a payout of $2.75 million.


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2024 Super Bowl LVIII

OVO again decided to dance with destiny by placing his biggest-ever wager of $1.15 million to back the Kansas City Chiefs to lift the Super Bowl by defeating the San Francisco 49ers. Also, the rapper wasn’t keen to “bet against the swifties.” To his luck, the Chiefs won the final, seeing him get a payout of $2.3 million.


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2024 Indian Premier League

For those unaware, IPL, or Indian Premier League is an Indian cricket league. Hence, this marked Drake’s first-ever bet cricket bet, where he placed a wager of $250,000 to back Kolkata Knight Riders (KKR) to clinch a victory over Sunrisers Hyderabad (SRH) to win the IPL final. His prediction, again came true as he pocketed $425,000.