Sports betting is a different world when it comes to the rich and famous. While the game has always been associated with high-street bookies and lucky punters watching the match at the sports bar, we’ve all seen those nail-biting mammoth bets slid in by some of our favourite celebrities taking part in the most tense and immersive way to enjoy sport.
Some celebrities make their betting habits more obvious than others, and a select few love to flaunt how often they dive in the deep end. Below, we’ve run through a list of the celebrities who are the biggest fans of sports betting out there, as well as some of their biggest successes – and worst fumbles – in the game.
Michael Jordan
Michael Jordan is one of the biggest names in celebrity sports betting, now that his public enthusiasm has earned him a place as the ambassador of a well-known sportsbook. One of the greatest basketball players of all time, Jordan also embraces his love of other sports in savvy betting, delivered with confidence and swagger. His favourite sport to bet on is golf, with Charles Barkley – another celebrity on this list – reporting that Jordan once dropped $300k on a single golf putt.
Floyd Mayweather Jr.
For Floyd ‘Money’ Mayweather Jr., it’s in the name. The big-hitting boxing champion is notorious outside of the ring for his extravagant bets – and he’s more than happy to share with his fans as well, frequently sharing winning slips on his social media. In 2015, the boxer went on an infamous four-day hot streak with the NBA, with staggering turnovers. However, there are rumours out there about his misses as well, despite the stacks of cash he flaunts online, with fans speculating he may have been down by close to $50 million one year in losses.
Charles Barkley
Another sports superstar who likes to dabble in sports betting off the pitch as well is NBA icon Charles Barkley, who’s sports betting experiences have brought him as many wins as his basketball career – and unfortunately, many wince-inducing losses as well. One of his most famous bets is scoring a win on a $500k spread favouring New England in Super Bowl XXXVI, netting him a payout of $800k.
Other bets haven’t gone quite so well, and Barkley has said he’s lost over $30 million gaming before he applied a little moderation. His outspoken love for the game has earned him some appreciation though – he now holds a spot as a sportsbook brand ambassador.
Charlie Sheen
Charlie Sheen’s known as a hellion in Hollywood, with his many vices driving him down the path of notoriety. Chief among these is the big-time sports bets he places, with his wife claiming he used to drop $200k every week on bets, following nothing more than his gut. These instincts once led him to place $1 million on Manny Pacquiao after he saw the win in a dream.
Soon after this, Sheen brought a close to his outrageous betting career and now considers himself retired.
50 Cent
Rapper 50 Cent has been a household name since he dropped his 2003 album Get Rich or Die Tryin’, and with that trigger-happy mindset when it comes to making it big, it’s no surprise the rapper is a relentless sports bettor and has brought home big win after big win. He’s won biggest on the NFL, bringing home $500k on a victory for the Giants over the 49ers in the playoffs, and won another $1 million wager on the Giants vs the Patriots in a Super Bowl game against producer Birdman.
While 50 Cent even raps about how his betting on boxing is a bit hit-and-miss, he still scored a win on his $1.6 million bet favouring Mayweather in the showdown between the undefeated champion and Manny Pacquiao.
Ashton Kutcher
Actor Ashton Kutcher has always been vocal about enjoying sports betting, but his name is on this list for his infamy. A scandal broke out in 2013 where he used his persona as the face for a huge betting syndicate that turned over about $750k in four weeks of college football. Betting companies caught on before long and blocked him, but the actor still enjoys betting honestly and for enjoyment alone.
Drake
Singer Drake has always made his love of sports known, cropping up in an array of jerseys for every sports team on the planet. Being that much of a sports fanatic, it’s no surprise that Drake’s making forays into the betting arena too. Unfortunately, as much as we’re sure Drake has won a good few wagers, he’s more famous than most for his fumbles, losing $6k each on two poor shots at the NFL and the NBA in two years running.
