Charlie Sheen, So Addicted To Gambling That He Didn’t Even Care When He Won A Million Dollar Bet | 10 Celebrities and Sportsmen Who Are Sports Bettors

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.


Sheen’s exploits in the sports betting world, first came to light in 2006 during his divorce with actress Denise Richards.

One of the reasons for her filing for divorce was Sheen’s gambling addiction, where she claimed he bet $200,000 every week. Not a bad reason at all.

Charlie Sheen's divorce

It was also claimed that he had some serious mood swings when he lost. Not sure if that’s because of losing a bet or the cocaine?

Either way, sports betting and Charlie Sheen didn’t mix well!


But there was one instance where they mixed quite nicely, and similar to a lot of celebrities, it came in the former of a big Boxing fight!

In an interview with the New York Times, Sheen revealed his biggest bet ever was on the bout between Manny Pacquiao and Oscar De La Hoya.

He put a whopping $1 million on Pacquiao to win, but his reaction to winning that bet was quite stunning:

“I had a dream a week before that he was going to beat De La Hoya like a drum, and he did,” he said.

“It was like, pfffft, whatever. I felt nothing.

“I went, okay, there’s nothing left for me here. Unless my children are involved in the wager, no sense in making it, you know?”

We’re not quite sure what he meant by including his children in the wager, but how on earth do you not celebrate a win like that!


At one point in 2011, Sheen, unfortunately, became a part of the other side of betting, when offered various betting markets on the celebrity.

Actor Charlie Sheen

This was during the time when Sheen’s antics were at their peak. Here were some of the markets:

  • Sheen to be arrested in the next 3 months @ 1.833 or 5/6
  • Sheen to be put in a mental institution @ 25.0 or 25/1

I’m sure this helped Sheen in his recovery from addiction and mental health...


After his lack of emotional response to his big win on Manny Pacquiao, this is when Sheen supposedly called it quits in the betting world.

In the same interview with the New York Times, he stated:

“I don’t bet anymore. I’m a retired gambler. Not a recovering gambler. Big difference,” he said.

“I’ll still look at the lines. I’ll be like, yeah, that’s a blowout, that’s a 40-point blowout. Easy, right? I’ll watch the game. It's a 40-point blowout the other way, and I can just walk away.

“I don’t have some dude calling, like, hey, yeah, so tomorrow, huh?”


That quote came in 2012, but by the sounds of it, that was not the end of his gambling addiction.

In late 2016, an illegal online sports betting ring, run by the Mafia, were busted.

During the investigation, several celebrities were caught on wiretapped conversations with some of the members who were arrested.

It has been rumoured that Charlie Sheen was one of a few notable celebrities who were on these tapes.

But even if the rumours are true, Sheen would not be punished with anything as US authorities generally don’t prosecute the customers of betting rings such as this.

Check out the other articles in our 10 Celebrities and Sportsmen Who Are Sports Bettors series on:

  • Article 1: Michael Jordan, the ultimate example of NOT having a betting strategy
  • Article 2: Ashton Kutcher, the 'dumb actor' who placed bets for the largest sports betting syndicate in America
  • Article 3: Floyd Mayweather, successful sports bettor or more trash talk?
  • Article 4: 50 Cent’s $750k bet that Floyd Mayweather couldn’t read a page of Harry Potter
  • Article 5: Pete Rose, the illegal gambler who cost himself $100 million
  • Article 7: Wayne Rooney, football legend and betting hypocrite
  • Article 8: Bryan ‘Birdman’ Williams, another celebrity lacking a winning sports betting strategy
  • Article 9: Charles Barkely’s horrible gambling philosophy, ‘lose hundreds of thousands, not millions’
  • Article 10: Ben Affleck, the movie star who learnt how to count cards

Want to read about some other professional sports bettors or some of our customers who are on their way to becoming professional sports bettors too? Take a look at some of these videos/articles:

  1. My Value Betting Journey from 1k to 2k
  2. 10 People Who Got Rich From Sports Betting
  3. Jonas Gjelstad Documentary Series - from $10k to $1m

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