10 Boldest Sports Bets Ever Placed by Rappers

10 Boldest Sports Bets Ever Placed by Rappers

Sports betting isn’t just for the casual punter. It’s a pastime that reaches the upper echelons of the wealthy. It’s not uncommon for example, to see celebrities sitting at high-stakes poker tables or egging other celebs into wagers.

There have been numerous examples of rappers taking big gambles on sports, with the likes of Drake, Jay-Z and 50 Cent all previously having hit the headlines with some wagers involving stakes that for most, would be life-changing sums of money.

While the casual punter looking at Match Center ZA probably isn’t going to be able to relate to the stakes involved, we look at some of the biggest and boldest bets that have ever been placed by rappers. Some of them returned staggering wins, but as highlighted here, if you bet big, you also run the risk of losing big.

50-Cent Backs Mayweather

One of the most famous sports bets by a rapper was when 50 Cent staked $1.6 million on Floyd Mayweather to beat Manny Pacquiao in 2015. It was one of the most high-profile boxing matches of all time, Pacquiao firmly believing that he could be the first fighter to beat Mayweather. He couldn’t. 50 Cent, real name Curtis Jackson, slapped the whopping sum down on the WBA and WBC welterweight champion Mayweather to win, and he did.

P Diddy Backs Mayweather

For the same Mayweather vs. Pacquiao fight, rapper P Diddy had $250,000 riding on the undefeated champion Mayweather, and the result of the phenomenally hyped bout went his way.

Jay-Z Loses on Cotta

Jay-Z had a misfire with a $100,000 stake on Miguel Cotta back in 2015, when the fighter, a Roc Nations Sports client of the rapper, lost to Canelo Alvarez. Alvarez, arguably the greatest pound-for-pound boxer of all time, won by a unanimous decision.

50 Cent Super Bowl Successes

50 Cent went in heavily with a series of bets backing the New York Giants to defeat the San Francisco 49ers in the 2012 NFL playoffs. The winning wagers reportedly returned him more than half a million dollars. The rapper then went ‘double or nothing’ on the Giants to beat the New England Patriots in Super Bowl 46 – which they did.

Birdman Undone by the Giants

In that same Super Bowl 46 encounter, there was no such good news for rapper Birdman. Tom Brady’s Pats not getting the job done was enormously costly for Birdman in an outrageous bet – he reportedly lost $5 million on the game by backing New England.

Drake Undone By Penalties

Drake has never shied away from big sports bets. For the 2022 FIFA World Cup Final, he went in with a $1 million stake on Lionel Messi’s Argentina to win the match. But the wager only covered the 90-minute result which ended in a draw. Argentina ultimately went on to beat France on a penalty shoot-out, but Drake’s huge stake was already a goner.

Drake Undone By Adasanya

Sticking with Drake, he wagered around $920K that MMA fighter Israel Adesanya would beat Sean Strickland by a knockout at UFC 293. Adesanya had been an odds-on favourite but was dramatically upset on points. Back at UFC 287 though, Drake had collected more than $2 million in profit after Adesanya had knocked out Alex Pereira in a middleweight title fight.

Diaz Denies Drake

Drake is back again on the list with another example of his sports betting picks being upset by an underdog. The Canadian rapper slapped $250,000 down on Nate Diaz to beat YouTuber-turned-boxer Jake Paul in a boxing match.

The wager would have returned more than $1 million to Drake, but Paul pulled off a shock victory over the MMA great in August 2023. In familiar territory, Drake also wagered $400k that Jake Paul would beat Tommy Fury in a boxing match in early 2023. Paul lost on a points decision.

Birdman Feels The Heat

Rapper Birdman doesn’t shy away from bold wagers. With the Miami Heat boasting superstar LeBron James, the musician backed the Heat to win the 2011 NBA Finals against the Dallas Mavericks. But it was the latter that took the series 4-2, costing Birdman $2 million in lost stake.

Brady Does It For French Montana

French Montana dropped $250,000 on Tom Brady’s Tampa Bay Buccaneers to beat Kansas City Chiefs Super Bowl LV. Brady, the NFL’s quarterback GOAT, did the business for the Bucs, guiding them to a convincing 31-9 victory over Kansas City.

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