Ray William Johnson: True Story Podcast
Charlie Sheen Sent a Woman to Prison - The Heidi Fleiss Story
19 Jan 2026
Chapter 1: Who is Heidi Fleiss and how did she start her escort business?
Do you remember when Charlie Sheen smashed with a bunch of escorts and then another woman basically got sent to prison for it? Now this story starts with this woman, Heidi. And Heidi is 22 when all this begins and she's living in Los Angeles. And Heidi, she loves two things, partying and money. Don't we all?
But one day in 1987, she gets the opportunity of a lifetime because she's out at a local nightclub and there she meets this woman, Madam Alex. And Madam Alex isn't just some regular woman at the nightclub. She actually runs an underground high-end escort operation in Beverly Hills, and she's been doing this for decades. So the two of them start talking.
And I guess Madam Alex sees something in Heidi. I mean, she's young and she's charismatic and she's a hustler. And at some point, she invites her to come work with her. And I don't think she wants her to become an escort. She actually wants her to help run the business. So Heidi sees this opportunity and she's like, hi. And so she goes to work with her.
And pretty quickly, she discovers that the money in the high-end escort business is insane. But she also sees that Madam Alex's whole operation is kind of outdated. Madam Alex uses the same escorts she's been using forever. I mean, these escorts, they're a bit older and the vibe is kind of stale and just the whole thing needs a reboot.
So, Heidi starts working to breathe new life into this business. And that's exactly what she does. She works to become Madame Alex's right hand. And within a few months, she's managing the entire business. So now, she's the person people have to go through. But probably the most important thing that she does is that she starts bringing in younger women to pimp out. Fresh-faced women.
Women who act proper. Women who appear classier to the client. And on the flip side of that, she is able to attract better clients. Wealthier men. Men who don't try to haggle or get weird about the prices or like want a freebie. Now, eventually, Heidi is pretty much running everything there. And because of all the changes she's implemented, Madam Alex is now making a lot more money.
Before Heidi got involved, Madam Alex was pulling in like $50,000 a month. But after Heidi's changes, Madam Alex is making like $300,000 a month. And that's great and all, but now there's a huge problem. Heidi feels like she's doing all the work while Madam Alex is making all the money. And on top of that, I guess Madam isn't paying Heidi as much as she feels like she deserves.
And this relationship goes on for years until around 1990 when Heidi finally says, it, I'm going to go start my own prostitution empire. And she quits working for Madam Alex and she goes and she starts her own escort business. And this ends up being a fairly easy move for her.
I mean, she's got a good business sense. She's got lots of connections to beautiful women who don't mind smashing in exchange for money. And she's also got connections with lots of wealthy men who are looking to smash. And so soon enough, she's booking tons of high roller clients, Hollywood men. She's booking global businessmen, billionaires, financiers. Sometimes she's even booking royalty.
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Chapter 2: What changes did Heidi implement to modernize the escort operation?
And that is when Charlie realizes the friend she's checking with is the madam and that these girls are all escorts. But that's totally fine with Charlie. Like he's actually kind of intrigued by it. And pretty quickly, he's got Heidi's number and he's calling her up and he's trying to pay for the services of two of her women at the same time.
And, you know, I guess he had his evening and that was a fun evening for him because soon enough he becomes a regular of Heidi's. And he books escorts for himself and sometimes he'll book escorts for his friends too. And over the course of three years, he spends around $53,000 on Heidi's girls using their services at least 27 times. And so Heidi's operation keeps growing and growing.
Here's the thing though, Heidi's not like other madams in the business, in that she doesn't seem to hide herself. In fact, she seems to be pretty open about who she is and what kind of business she operates. But whatever, there doesn't seem to be any known threat of her getting busted or anything like that anytime soon. Until 1993.
That year, one of Heidi's escorts, this woman, Datig, Datig decides that she wants to leave the hooker business and pursue her dreams of becoming an actress and a model. And Heidi's like, eh, not so fast. Heidi doesn't want her to leave because, you know, all the money she's bringing in. So Datig gets worried that Heidi is never going to allow her to leave.
So she goes and she reports her to the police. So now police have caught on to Heidi's prostitution ring and they set up a whole sting operation to bust her and four undercover police officers pretend to be Japanese businessmen and they hit up Heidi and they order four of her escorts to meet them at this local hotel.
So then I guess Heidi brings four of her girls to the spot and as soon as they get in that hotel room and one of the ladies starts getting naked... Bam, police bust in and they start arresting all of them, including Heidi. And I don't have a mugshot of her, but here is another picture of her. Now, when they arrested her, she had a bag on her with a planner in it.
And in that planner, police find several traveler's checks made out to her from none other than famous actor Charlie Sheen. So now police know that Charlie Sheen was a regular client of Heidi's. And so they call him in and they basically threaten to charge him with felony pandering or hiring a prostitute.
So in exchange for immunity, Charlie agrees to snitch and testify against Heidi and essentially expose her for being the operator of this illegal escorting business. And so they all go to trial and Charlie testifies against her and she's found guilty. However, due to some juror misconduct, her convictions actually get thrown out.
But then in 1996, she gets charged again, this time for tax evasion, because I guess she wasn't paying all her taxes. And this time she gets sentenced to seven years in prison.
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