After the success of our article series on 10 People Who Got Rich From Sports Betting, we wanted to take a look at some celebrities and sportsmen who also do a bit of sports betting on the side!

Now they might not be as successful as the likes of Tony Bloom or Matthew Benter, but their betting stories are just as good! Enjoy the series!

ARTICLE 1: MICHAEL ‘AIR’ JORDAN

Just like sports betting professional, Billy Walters, Jordan would frequently make bets on the Golf course with his friends.

Unfortunately, in Jordan’s case, most of the time it was more like a gamble, as having a bet would suggest he had some kind of strategy.

Jordan has some pretty crazing betting stories, read about them all here!

ARTICLE 2: ASHTON KUTCHER

Unlike a lot of celebrities involved in the sports betting world, Kutcher has been extremely successful for one reason; he has a strategy!

Kutcher doesn’t gamble his money away for a quick thrill, he is a strategic sports bettor who uses mathematics and science to make decisions.

He also fronted the biggest sports betting syndicate in America, read all about it here!

ARTICLE 3: FLOYD ‘MONEY’ MAYWEATHER

As you can tell by his nickname, Floyd’s mantra is based around making money, so it’s no surprise that he was recently named the highest-paid athlete of the past decade by Forbes, earning more than $900 million during that period.

Mayweather loves to flaunt his earnings to the public, revealing his latest purchases all over his social media, and he takes a similar approach to his sports betting.

He also posts his winning bet slips for the public to see, which was most evident in the early stages of the past decade.

Read the whole article here!

ARTICLE 4: CURTIS ‘50 CENT’ JACKSON

Similar to Floyd Mayweather, Curtis ‘50 Cent’ Jackson is another example of someone who loves to flaunt his betting activities on social media.

But contrary to Money Mayweather, he doesn’t mind highlighting the darker side of gambling. Not only has ‘Fiddy’ written lyrics such as, “I got a gambling problem” and “I lost money when I bet on Roy,” he also spoke about it in 2006.

"I gamble too much, I gamble for too much money and it's something I have to address,” he said.“I've got to realise no matter how much I win, it ain't a lot—it's only a lot when I lose. And you always lose. I think it's fun, I think it's exciting. I'm gonna continue to do it but I have to get to a point where I don't try to break the casino, 'cause you never can."

Read the whole article here!

ARTICLE 5: PETE ROSE

Unlike the other celebrities and sportsmen who we have featured in our series so far, Pete Rose was involved in the darker, more illegal side of sports betting.

Before finding himself in a legal mess, Rose was considered one of the greatest Major League Baseball (MLB) players of all time.

He is a 17-time All-Star and three-time World Series winner, along with holding records such as the leader in games played and all-time hits.

But in 1989, his legacy would be forever tarnished, when MLB commissioner Pete Ueberroth announced that Rose was under investigation over “serious allegations”.

Read the whole article here!

ARTICLE 6: CHARLIE SHEEN

Out of all the famous Celebrities and Sportsmen we’ve featured in our Top 10, I’m sure you’re the least surprised by the inclusion of Charlie Sheen.

Famous for his starring role in Two and a Half Men and his addiction to drugs, alcohol and sex, it has also come to light that you can add gambling to the list.

From rumours to being involved with a Mafia-led betting ring and winning big on boxing fights, here is the story of Charlie Sheen and sports betting.

Read the whole article here!

ARTICLE 7: WAYNE ROONEY

Over his 16 years in the Premier League, Wayne Rooney amassed 208 goals in the EPL with both Manchester United and Everton, including 5 titles with United.

He also scored 53 goals for England, in a career that has not yet finished, as he recently signed for Derby County as captain, who play in the Championship.

But the reason we’re talking about Rooney is because of an interview he did in early 2020, where he revealed his struggles he’d had with gambling during the early stages of his footballing career.

In light of his admission, it has made his new deal with Derby County not only controversial, but it makes him look like a hypocrite!

Read the whole article here!

ARTICLE 8: BRYAN ‘BIRDMAN’ WILLIAMS

Number 8 in our 10 Celebrities & Sportsmen Who Are Also Sports Bettors series, comes rapper and Cash Money Records co-founder, Bryan ‘Birdman’ Williams.

Although Birdman is not the biggest in the world of rap, he is for sure one of the richest, with an estimated net worth of $100 million.

His label, Cash Money Records, has included the likes of Nicki Minaj, Drake and Lil Wayne over the years.

But the reason we’re talking about him is because, like a lot of celebrities, Birdman gambles way too much money on sports!

Read the whole article here!

ARTICLE 9: CHARLES BARKLEY

Legendary Basketballer, Charles Barkley, once famously outed Michael Jordan for betting $300,000 on a single hole of golf, but ladies and gentlemen, we’re here to tell you that Barkley himself is not much better when it comes to gambling!

Barkley retired from the NBA in 2000, finishing his career as only the fourth player in history to achieve 20,000 points, 10,000 rebounds and 4,000 assists.

But perhaps nowadays, Barkley is more famous for his work off the court, whether that be as an NBA analyst or quite possibly the worst gambling sportsmen of all time!

Read the whole article here!

ARTICLE 10: BEN AFFLECK

Unless you’ve been living underneath a rock, you have probably heard of this guy before!

Ben Affleck has starred in some of Hollywood’s biggest films, from Good Will Hunting, to Batman, to Gone Girl, he’s done it all!

But what you might not know about Affleck is his relationship with gambling, more notably, his time at the Blackjack and Poker table.

Unlike most of the celebrities we have talked about in our 10 Celebrities & Sportsmen Who Are Sports Bettorsarticle series, Affleck has actually been quite profitable!

Read the whole article here!

Check out our other article series on 10 PEOPLE WHO GOT RICH FROM SPORTS BETTING!

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