Charlie Sheen – Gambling Bad Boy

Charlie Sheen (real name Carlos Irwin Estévez), famous American actor, always seems to be in the limelight for his vices, including womanizing, drinking and substance abuse. So, it comes as no surprise that Sheen’s ex-wife Denise Richards claims he had a severe gambling addition, regularly spending more than 200000€ a week to satisfy his cravings. It’s been said, however, that he’s since cleaned up his act.

Blog » Charlie Sheen – Gambling Bad Boy
  • Charlie Sheen blew nearly 200,000€ a week on both sports betting and casino gambling. But early 2011, Sheen confirmed that his gambling days were over. That’s one addiction less, but he has not given up on cocaine and alcoholic beverages […]
  • In 2011, a 2.2€ million proposition bet was made between two professional blackjack players regarding the gambling future of Charlie Sheen […]
  • In 2019 Sheen stated that he overcame his addictions and celebrated being over one year sober […]

I exhausted it completely. The only thing left would be something catastrophic… Every other time (I was sober) I was led there through intervention or rehab or a detox. This last time – the last time – I couldn’t get my daughter to an appointment she had

Charlie Sheen on his down times

American film and TV actor Charlie Sheen has a dubious reputation due to several addictions, including compulsive gambling. However, the notorious womanizer claims he doesn’t gamble anymore. Charlie Sheen used to spend large sums of money at casinos, while he also loved to bet on sports events. The actor bet on sports every day, with highs and lows in the hundreds of thousands of dollars. His passion for gambling was one of many addictions, varying from drugs, alcohol and sex. It appears that Sheen has quit gambling and betting, but you can never trust an addict.

Sheen for Halloween!
Sheen for Halloween! Killer cartoon by “San Diego Union Tribune”

Out of Control

The American bad boy starred in several television series and movies, but he is best known for his starring role in the hit TV series Two and a Half Men. Some years ago, Sheen was even the highest-paid American actor, pocketing around 1.6€ million per episode of Two and a Half Men, and he was fastest to reach 1 million followers in Twitter back then (both of those facts were Guinness World records actually). Charlie did a lot for HIV prevention and diagnosis (“Charlie Sheen Effect”). In March 2011, Warner Bros Television fired him after a number of controversial interviews.

One addiction overcome

His detractors claim that Sheen became addicted to gambling in his youth. In 2006, his ex-spouse Denise Richards revealed Sheen’s out-of-control gambling. She claimed that he blew nearly 200,000€ a week on both sports betting and casino gambling. En route to the hospital, for the birth of their child, Richards claimed, Sheen placed a call to his bookie to bet on a sporting event. But early 2011, Sheen confirmed that his gambling days were over. That’s one addiction less, but he has not given up on cocaine and alcoholic beverages. Maybe, though, he was just approaching it the wrong way. Sheen’s brother Emilio Estevez made the most of his gambling by serving as the big player for the blackjack team run by Rob Reitzen, one of the most successful gamblers in history.

Following his public meltdowns Sheen started his own gambling business in the form of gambling internet website. Yet no more information on his success or failure in this case is available.

QUESTION FOR YOU

Have you ever heard how Sheen’s gambling website was called? And what about business results – was it success or failure for Sheen? We haven’t managed to find information regarding these matters, but maybe we don’t know where to look? If you know or heard some rumours about these matters, please share them with all of the readers in the comments section below. Big thanks!

Bet On His Gambling Future

In 2011, a humongous 2.2€ million proposition bet was made between two professional blackjack players at All Slots Mobile Casino regarding the future of Charlie Sheen. The complete details have not been fully revealed, but people in the know state that – ‘it’s a multi-part bet made during a chat at a mobile casino. Mr Sheen must reach three separate milestones, each within a certain time frame,’ for the bet to be won. With the calibre of the people involved, this is a serious matter, as solid as a written contract. The outcome of this bet is also unknown.

Ready to work?

Mr Sheen those days casually spoke with a number of tabloids, as well as mainstream media, about his recent crack and whoring binges. He showed off his porn star ‘Goddesses’, his gnarly friends and every toy a multi-millionaire who is the master of his own domain can buy.

Mr Sheen, despite looking a bit worn down, to say the least, proved that cocaine is not in his blood and that he is ready to return to work. Yet, after not so nice remarks about the show’s creator, Mr Chuck Lorre, as well as other producers, there was only a 10% chance of the show returning.

Did someone say 10%? You want to put some money on that?

One Year On Sober

As we can clearly see Hollywood’s Charlie Sheen has had a colourful past with alcohol and drug abuse, but in 2019 he spoke to Loose Women about how he overcame his addictions and celebrated being over one year sober.

Charlie Sheen in attendance for Charlie Sheen at Prive Nightclub, Planet Hollywood Resort & Casino, Las Vegas, NV, October 25, 2008
Charlie Sheen in attendance for Charlie Sheen at Prive Nightclub, Planet Hollywood Resort & Casino, Las Vegas, NV, October 25, 2008

Sheen said he feels like a completely different person than he used to and revealed he’s been sober for over a year now and has been in therapy. He’s also keeping things more low-key. He said he’s got a strict rule of no more than five guests at one time in the Sheen household to reduce his chances of feeling an urge to drink. 

“There’s nothing left in that world,” he said of his past drinking habits. “I exhausted it completely. The only thing left would be something catastrophic… Every other time (I was sober) I was led there through intervention or rehab or detox. This last time – the last time – I couldn’t get my daughter to an appointment she had.”

Sheen recalled being drunk and calling a friend to drive his daughter (“I don’t drink and drive ever”). He later realized that his actions were deterring him from being present for his children. 

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“The next morning I just woke up and said, ‘today’s the day.’ And that was it,” he said. 

Detailing the “tough but not impossible” process of saying sorry to loved ones he wronged, Sheen said he got “tired of apologizing for things you can’t remember doing.

“The amends can’t just be words, they have to be actions… But you make them when it’s appropriate. It’s not about making them on your terms, it’s about approaching others on theirs.” 

Sheen doesn’t have any entertainment projects in the works but says he remains optimistic about moving forward with his life and re-entering the workforce.

“I essentially have nothing to promote today, but I thought about that and actually I do have something to promote: I’m promoting sanity,” he said. “I’m promoting a sense of nobility and a return to a more innocent place and just gratitude and knowing that whatever comes next, work-wise, that the version that I will deliver will be spectacular.”


Updated on 2020-09-10. These are best-known stories about Charlie Sheen’s addictions and gambling. Do you know more? Post some hints in comments below and we will add more interesting stories about him here.

To be continued …

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