Heidi Fleiss Is Finally Ready to Rat Out a Client. But Why? 
Illustration by: Owen Freeman

Heidi Fleiss Is Finally Ready to Rat Out a Client. But Why?

On the 20th anniversary of her release from custody, Hollywood’s most famous madam invites The Hollywood Reporter to her desert bird sanctuary to spill a wild story, in the process revealing a bizarre and drug-filled lifestyle and zero interest in a post-#MeToo image rehab: "I’m not that likable."

At the far edge of Pahrump, Nevada, where unpaved roads narrow as they rise toward the desert mountains, Heidi Fleiss waited, intent on settling a score. The once-powerful Hollywood madam, whose high-profile clients included stars and executives, was arrested in 1993, sent to federal prison and freed 20 years ago this September. Now she had summoned The Hollywood Reporter to the remote bird sanctuary where she lives alone with dozens of rescued parrots. Look for a structure that recalls both Robinson Crusoe and a haunted house, she had texted: "it says do not enter. turn there."

Inside, the birds squawked the non sequiturs they'd learned from abusive previous owners. One constantly shrieked "Fuck!" Another, no matter the circumstance, repeated "I love you!" Their "nanny," as Fleiss referred to herself, tended to them. When they quiet after the sun sets, Fleiss, 53, sleeps beneath them. Lately, though, she had not been sleeping easily. She had been wronged, she claimed. She wanted revenge.

Fleiss, her cosmetically enhanced lips now deeply cracked, has long maintained a reputation for discretion. In her heyday, when she serviced the likes of Charlie Sheen, she never spoke about her prominent clientele, who paid a $1,500-a-night base rate and tipped, she claimed, up to $1 million. (Fleiss took a 40 percent cut.) When Radar reported that high-profile men including Johnny Depp, George Lucas and Robert Evans appeared in the pages of Fleiss' so-called "little black book," though without evidence they actually used her services, she refused to engage. She didn't talk after the LAPD busted her at her Benedict Canyon compound, nor at her trial, which became a '90s media frenzy rivaled only by the O.J. Simpson and Monica Lewinsky sagas.

"It was the Hollywood, the sex, the drugs. It was everything that makes a good story great," says Hollywood, Interrupted co-author Mark Ebner, who reported on the Fleiss scandal. "She was young and attractive and a loose cannon. But when you get down to what she was doing, it was no different than what a pimp does." The world's fascination was at least partially fueled by Fleiss' irreverent candor. ("If you're going to run an illegal business, you better be driving the best car, living in the biggest house, fucking the best-looking people and spending every dollar you make," she later philosophized, "because sooner or later you're going to get caught.") But the one thing she was never candid about was her clients.

Then, in October, Fleiss made an exception to her underworld ethic. She wanted this publication to out one of her longtime friends — a wealthy Hollywood businessman — who she alleged had betrayed her. According to Fleiss, the man, whom she has known since her prime, had made a deal with her: If she would discreetly pay off his prostitution debts using her own funds, he'd reimburse her and contribute exponentially to her bird sanctuary. (Fleiss said she had not helped the man procure these sex workers in the first place, but was merely tasked as his clean-up woman.) Now, several years had passed and the man had not made good on his promise. This offense had become Fleiss' obsession. "I feel denigrated, used, taken advantage of by a very rich man," she told THR. "It sickens me." As she spilled on her friend's indiscretions, sharing photos, texts, emails and other material that she said corroborated her claims, Fleiss also opened a window into her own existence.

Today it's possible to view Fleiss as a cautionary tale of industry excess and Hollywood's patriarchal tradition of using women and then discarding them when they've lost their usefulness. (Recall that none of her clients was prosecuted.) Yet despite the culture's current reconsideration of sexual power and victimhood, Fleiss herself insisted that she wants no part of a redemption narrative. She rejects the wave of sympathetic reconsiderations that have allowed fellow '90s-era single-monikered national villainesses — Monica, Lorena, Tonya — newly burnished platforms as empowered female icons.

"I'm not that likable," she said flatly. "If you accept that, everything is so much easier. If you care what people think, you're their prisoner."

In fact, when it comes to #MeToo, Fleiss is downright dismissive. In the case of those who have accused Harvey Weinstein, she wondered which of them might retroactively have regretted their encounters with the mogul because their careers didn't pan out afterward quite as they were promised. She was especially bemused when the ill-fated hustling came to light between filmmaker Brett Ratner, financier James Packer, former Warner Bros. CEO Kevin Tsujihara and his apparent mistress, who angled for acting roles by playing them off one another. "That's what happens when they try to do my job," she joked. Fleiss then asked for Packer's contact information, wishing to pitch him on financially assisting her birds. After all, his late father, Australian media tycoon Kerry Packer, was once a top client, she claimed, who'd "give a million dollars for five girls to split." (Packer's use of Fleiss' services surfaced during her trial.)

Fleiss has long struggled with substance abuse, recently favoring the combination of a snorted line of methamphetamine paired with a Xanax. "I'm a snobby drug addict — I don't smoke it," she explained of the meth. By her account, her fragile sobriety had been further compromised by grief over the October death of her former lover and longtime friend Dennis Hof, the Nevada brothel baron ("I keep slipping," she said), as well as her anger at her friend turned nemesis. "I've never had a problem with any client, ever, except for this one," she said. Fleiss was especially aggravated because she believed the man had leveraged her virtue of secrecy against her: "He knows I haven't ratted on anyone, that I don't talk." Now, she claimed, she had no choice — even if it meant exposing herself to charges of blackmail and renewed unflattering attention.

Fleiss was candid about how erratic and conspiratorial she came across over text and email, as well as her habit of rambling. She attributed her behavior to Suboxone, a prescription narcotic she'd been taking to fight opioid addiction. Its side effects can include concentration problems.

For income, Fleiss has several hustles. Every so often, a reality TV show like Celebrity Rehab With Dr. Drew will ask her to appear for a fee. ("I'm like, 'Great, $500,000 for being a drug addict — this is phenomenal.' ") She previously experimented with growing marijuana on her property, but her steady gig is flipping Airstreams anonymously on eBay. Fleiss, inspired by how Sean Penn lived in Malibu in one, began hunting them down around Pahrump. (Her neighbors see little aesthetic value in the trailers, now so beloved by Instagram influencers.) She farms out basic rehab work and sells them for four times the purchase price. "This place is just a dumping ground for them," she said of the town that enables her to maintain her birds. "It's the ugliest community on the planet, and I've been all over the world. It's Wonder Bread and Velveeta cheese."

Several years ago, she'd invested a $1 million inheritance from her father into Bitcoin, intending to use it to support herself and her birds. In February, she filed a $4 million lawsuit against another former friend, alleging cryptocurrency theft. "I don't wanna come off as like a … serial fuck-up," she wrote by email shortly afterward. "Maybe I am. I just make really bad decisions."

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Fleiss' fervor for birds was ignited when she first moved to Pahrump in 2005 to open a much-publicized "stud farm" for women willing to pay for sex — neighbors objected and the bordello never got off the ground. At the time, she lived a short distance from her current home. Her bedridden, elderly next-door neighbor Marianne, herself a onetime prostitute and former madam ("She got girls for Howard Hughes; Colonel Sanders was her sugar daddy"), kept a caged aviary of dozens of parrots in a single-wide trailer. Fleiss fell for one of them, a male named Dalton. "I just connected," she said. "It really bothered me that he'd been sitting in that cage for 15, 20 years. There was dust on him."

When Marianne died soon after, Fleiss took possession of "Dalt" and a few other birds and sought to place others in a sanctuary. "I found that there really weren't any that were truly what you think of when you think of a 'sanctuary.' It would be a lady with an apartment in a San Bernardino complex with a second bedroom and a 501(c)3 [nonprofit registration]," she explained. So Fleiss decided to build and operate a more enlightened safe haven of her own. "I thought running 500 girls was hard," she said. "That was nothing."

Fleiss now manages about 40 parrots at her indoor-outdoor spread. None of the sanctuary residents is caged, living instead beneath an intricate latticework of netting. They come and go as they please, though only a few of the second-generation ones, those who were born under Fleiss' care, will fly beyond the property line. These free birds like to take flight across town to Treasure RV Resort, landing by the pool and palm trees. "People Facebook it," she said.

Many of Fleiss' parrots have been misshapen by trauma before her time with them. There's the one that was given poppers, or amyl nitrate, an inhalant. Another spent its life in a closet, trained to spout "Look at that!" when the door opened. A third has a metal pin holding one of its feet together because he was thrown against a wall. "The life span for parrots is getting shorter, which is good because then the torture in cages is not as long," she reasoned, before explaining that she had gone as far as breaking into a house to retrieve an abused parrot. "Really, the best thing is for the species to go extinct. A dog lives 13, 14, maybe 18 years. These birds live human life spans, all cooped up." Fleiss added that she is acutely worried about dying because she believes the precarious refuge she's created will dissolve as soon as she's gone. Animal control authorities will "box them all up and stick them in kennels," she said, her voice quavering.

Fleiss' Pahrump operation is low-overhead. It's just her — she lives on site, making regular road trips to L.A. to buy hundreds of pounds of feed — and a Salvadoran family living around back whom she pays to clean. But she's hoping to hire folks to handle marketing and fundraising, and if she can ever afford it, purchase a more appropriate 200-acre property in Oregon that she's had her eyes on. "It's all trees," she said.

The man Fleiss alleged betrayed her wasn't her only would-be parrot benefactor. There was the late Simpsons co-creator and noted animal rights activist Sam Simon, who by her account was impressed with her pitch in the days before he was diagnosed with terminal cancer. "I couldn't follow up with him afterward," she said. "It didn't seem right." Then there was high-flying Relativity Media founder Ryan Kavanaugh, who'd owned an African gray parrot before his own financial flameout: "He was going to help me, then he went bankrupt," referring to Relativity's 2015 collapse. She exhaled, long and slow. "How do I have such bad luck when I'm trying to do good things with these birds?"

***

By the time Fleiss approached THR in October intent on vengeance, she said the man's attorney had actually paid her back in full (approximately $220,000, she claimed). Yet Fleiss still wasn't satisfied — she wanted the donation for the bird sanctuary, she said, and her incessant demands for the money had angered him. At a mutual friend's L.A. apartment party in August, "he was threatening to hurt me. He says, 'You live out there in the middle of nowhere. Accidents happen all the time.' "

Fleiss continued to press her case against the man to THR until March. Then something happened. Following a week of silence, she forwarded a letter that appeared to be ghostwritten for her by an associate of the man. (She neglected to remove the associate's email address.) It explained that she would no longer be "going forward with the story," adding: "I was very mad at the person we discussed. I was furious in fact and as a result I made up the stories I told you." The letter went on to observe that she was high during THR's February visit to her Nevada property, recanting everything she'd claimed and that she'd provided evidence to back up. The reason still isn't clear, and she dodged further questions, instead repeatedly indicating that her decision was informed by a realization that THR wouldn't "run a photo that is an accurate depiction of what macaws endure."

Maybe a threat changed her mind. Or she was lying. Or perhaps, having convinced the man she was serious about telling her story, he finally yielded and paid out what she desired. (Because of the murkiness of her actions and other credibility issues, THR withheld the man’s identity in this story.)

With Fleiss, when it comes to sex, money and power, there remains a blurred line between being the exploited and the exploiter.

In 1995, as Fleiss was out on bail and awaiting sentencing in her criminal case, British documentarian Nick Broomfield probed the circumstances of her downfall. He found it was the result of Fleiss' naivete. First she'd usurped the clients of a long-established Hollywood predecessor, known as Madam Alex, while working in tandem with a wily boyfriend, the late B-movie director Ivan Nagy. Then she decided to go solo, antagonizing Nagy, who took revenge by asking sex workers loyal to him to snitch on her to law enforcement. (Unlike Fleiss, Madam Alex knew how to protect herself: She was a valued veteran informant for the LAPD vice squad.)

Broomfield learned from Nagy that, after the trial, Fleiss was still in communication with him, even visiting his apartment. A quarter-century later, she'd maintained a similar, ongoing rapport with the man she said had betrayed her, even in the midst of threatening to go public about him. Reached in May, Broomfield offered a theory on Fleiss: "Her choices in people are self-sabotaging. She's her own worst enemy." In both cases, Fleiss was asked why she kept in close contact with those who had hurt her. Now, as then, she had no answer.

This story first appeared in the May 29 issue of The Hollywood Reporter magazine. To receive the magazine, click here to subscribe.