Dylan Howard was the volatile actor's confidant until the National Enquirer editor began investigating rumors that Sheen was HIV positive. Then it was war. And that’s a story, told here for the first time, almost too crazy to believe.
This story first appeared in the April 22 issue of The Hollywood Reporter magazine. To receive the magazine, click here to subscribe.
It was a Friday afternoon in early September 2014. As editor-in-chief of the National Enquirer and RadarOnline, I was used to rubbing celebrities the wrong way. Sometimes they get mad, ordering a public relations flunky or manager to get in touch with a self-righteous denial. Sometimes they threaten litigation.
But this was different. This was insane.
I picked up on the third ring, and he launched straight into it. "You want to fucking go down this road, you fucking douche bag?"
The voice was hoarse, cracking with fury — but I recognized it immediately. Charlie Sheen: the man with whom I had enjoyed a working relationship for more than three years, since before his dismissal from Two and a Half Men — and subsequent meltdown — had made him the hottest source of copy in my career.
What had happened? Last time we had spoken, things had been amicable. Now, barely drawing breath, he ranted on: "You motherfucker. You want to fucking, like, sit over there and fucking insult my fucking gal like this? Fucking whore. Come to my fucking house today. … Come to my fucking house today, you fucking pig."
I racked my brain. What was the last big story we'd run on Sheen? Nothing came to mind. "What's the issue?" I asked. "I don't know what your issue is. What's your problem?"
"Go hug your fucking parents, OK?" he yelled. "I don't care if they're dead or alive. Dig them up and hug their decaying corpses. You motherfucker. How fucking dare you? You fucking hurt the last fucking thing you should hurt. One more story, bro, and you'll wake up looking into my fucking eyes, you fucking whore pig. I fucking dare you. Now it's a challenge. I fucking dare you." Then Charlie hung up.
I still wasn't sure which story he was mad about (it turned out to be an innocuous piece in which one porn-star ex expressed doubt about the long-term prospects of his relationship with his latest porn lover) — but something else was going on.
The truth was, I had been chasing a Sheen story for years. A story so big, it would change both our lives forever.
Fourteen months later, the Enquirer broke that story: Sheen was HIV positive. Not only that — he had known for four years. His wild lifestyle likely had exposed countless girlfriends, models, porn stars and prostitutes to unspeakable risk.
It also was a story of extraordinary corruption, violence, lies, intimidation, death threats and millions of dollars paid out in hush money — a story that only now can be told.
I entered Charlie's orbit in October 2010. After a journalism career in Australia and at Reuters in New York, I had joined RadarOnline to head up the entertainment website. Sheen, now 50, already was big news — as the star of Two and a Half Men, he was the highest-paid TV actor in the world, with a well-documented history of hard partying and domestic violence.
He had spent the previous Christmas Day in jail after police were called to an address in Aspen, Colo., by his third wife, Brooke Mueller, who accused him of choking her and putting a knife to her throat. Charlie was charged with second-degree assault, menacing and criminal mischief. In 1997, he had pleaded no contest to a charge of assault on former girlfriend Brittany Ashland, and in a sworn declaration during their 2006 divorce, second wife Denise Richards declared Sheen to be unstable, violent and addicted to gambling and pornography. She also claimed he assaulted her, shoving her to the ground and screaming, "I hope you fucking die, bitch!"
And now I was going to be a part of the story. A woman once propositioned by the star had given Charlie's cellphone number to a source of mine — and soon I had a perfect opportunity to use it.
On Oct. 26, during what was supposed to be a vacation at New York's Plaza Hotel with ex-wife Denise and their two daughters, Charlie lost it again. After a wild party in his suite with porn star Christina Walsh (aka Capri Anderson), the actress called security in a panic. Sheen had gone crazy, she said. He was drunk, high on cocaine. He had locked her in the bathroom and trashed the room. He was yelling that she had stolen his $170,000 Patek Philippe watch, and she was afraid for her own safety.
The cops arrived. Charlie was taken to a hospital for psychiatric evaluation. And as the story made its rounds, it was my texts he eventually replied to. "Oh my man, I'm fine," he texted me. "The story is totally overblown and overplayed as far as the reality of the scenario. … I know what went down and that's where it will stay … under wraps."
His publicist claimed that no alcohol or drugs were involved — simply that "Charlie had an adverse allergic reaction to some medication."
In February, I texted Charlie in the Bahamas, where he was holidaying with Brooke and his two "goddesses," porn actress Bree Olson and model Natalie Kenly. Warner Bros. was abandoning shooting of Two and a Half Men, I told him. There were credible allegations that he was using drugs again — specifically, crack cocaine.
Sheen was furious. "Fly down here and test my pee. Lies are the fuels that cowards drink. How's it taste? When it's clean? Then what? Yeah, thought so. Pussy."
I met the challenge head-on. "You're 45," I wrote back. "It's about time you acted like it. If you want to call our bluff, we will fly to wherever you are and do the test and report if you are clean or not. If you want to prove the detractors wrong, then let's do this."
His reply was instant. "If you sign an agreement to DRINK it when it's clean then we are on. Plus, I get to film it. … Drink it. Fuck you c—. Who do you think you are?"
And so I found myself in Charlie's palatial Sherman Oaks mansion on Feb. 28, 2011. I was there to conduct an interview and to witness two drugs tests — a home urine test and a blood test conducted by a court-certified California laboratory technician — covering marijuana, cocaine, opiates, amphetamines and alcohol.
He greeted me with a bear hug. "You've got balls, man," he said. "You've got big balls. Let's bury these naysayers. Let's make these trolls and fools go away forever. Let's just do it. Let's meet it head-on. You were in it to win it. With everything going on, I decided it was the right thing to do, and I found a guy who was as excited about it and who was as intense about it as I was, and I knew we were the right team to handle this." It was a typically florid Charlie rant, but the implication was clear: As far as Charlie was concerned, I was part of his team.
The tests came back negative. On Feb. 28, 2011, I appeared on Good Morning America, results in hand, and declared, "This is a big win for Charlie Sheen." I'm no longer so sure.
Sheen (left) with The National Enquirer editor-in-chief Howard in 2011. (Courtesy of Howard)
Over the following month, I became a regular at his home — the so-called "Sober Valley Lodge." I was on first-name terms with his entourage: trusted lieutenant Rick, manager Mark Burg, his goddesses, a whole crew of sycophants, flunkies and hangers-on.
One night I received a call from Charlie begging me to come to the house. "The cops have turned up," he said. "They're taking away the kids." Mueller had obtained a restraining order against Sheen, and social services was there to remove their twin sons from his home. ("Film it," I told him.)
Later that night, once the children had gone, Charlie sat down to show me what he said were photos of Brooke's drug paraphernalia on his iPhone. He left me with his phone as he crashed out with his goddesses.
I sat in the study, surrounded by millions of dollars of baseball memorabilia (including one of Babe Ruth's World Series rings), scrolling through his camera to download and send the photos. But the device also was crammed with nude pictures of hookers, porn stars, random pickups … and several paparazzi photos of Hayden Panettiere.
His trust in me was bizarre. He had sacked his longtime press agent and appointed himself as his own publicist — and he was using me to present an image to the world. And every moment of madness, every tale of machete-waving and goddess-bedding, every tiger-blood rant and hard-partying revelation I published reinforced his own twisted, exaggerated, narcissistic brand. Hashtag winning, as he might have put it.
We made a short film together called Operation Greyhound — in which he lampooned his father's masterpiece Apocalypse Now while trying to "rescue" his trailer from the Warner Bros. lot (it's still on YouTube). He gave me personalized "Vatican Assassin" dog tags — and a set of walkie-talkies so we could be in constant communication.
Another night, he invited me over to watch a TV interview — the now-infamous 20/20 episode in which he declared: "I am on a drug. It's called Charlie Sheen. It's not available because if you try it once, you will die. Your face will melt off and your children will weep over your exploded body."
Suddenly, he insisted on doing another drug test. "We gotta do it now," he yelled — and during an ad break, he dragged me into the bathroom, passed me an empty water bottle and had me hold it while he relieved himself. On the shelf was an over-the-counter testing kit. He passed again.
Still, I was increasingly uncomfortable being part of Charlie's world. I did not want to be seduced by the supposed glamour and money. There was desperation at its core. And I knew he was manipulating me.
But what if I got ahold of a story he didn't want the world to know?
Howard first met Sheen at his Sherman Oaks mansion in February 2011 and was greeted with a bear hug. Later that day, he watched Sheen take two drug tests that he now fears were rigged. (Illustrations by William Walsh)
I put together a "ghost team" of reporters, and we started investigating. If the story was true, it was a bombshell: Many of Charlie's hundreds, possibly thousands, of lovers would have been exposed to the virus.
What we uncovered was shocking not only in terms of illuminating the depths of Sheen's depravity but in the scale of the conspiracy to hide the truth. What had started as casual PR manipulation had escalated into what was beginning to look like a monumental cover-up.
It soon became clear that Charlie's sexual appetite was not limited to wives, goddesses, porn stars, prostitutes — or even women.
Digging revealed that the Aspen Christmas incident, in which Charlie held a knife to Brooke's throat, wasn't the simple domestic dispute it had been painted as. I was able to examine texts between Brooke and a secret lover that revealed a darker story. Charlie was also having sex with that same man at the time — and Brooke was secretly photographing and videoing the crack-fueled encounters. Her motive? Leverage.
Charlie's Christmas Day explosion came after she told him about the tape — and threatened to publicly release it unless he tore up their prenuptial agreement and paid her $55,000 a month in child support.
He held a knife to her throat because he didn't want the world to know he had homosexual sex — and because he hated the idea of anyone getting one over on him. (He later told me: "I have never felt so powerful before in my life. That bitch deserved it.")
The iPhone photos of Brooke's crack pipes and other paraphernalia he showed me at his mansion? A preemptive strike. Insurance against whatever photos she might have of him.
I read texts between Brooke and her (and Charlie's) lover that show Brooke was obsessed with a fear of catching HIV. "Please b honest," she writes. "Do u have HIV or hep c?" When he replies in the negative, she continues, "When was the last time u got tested?" And later: "Ur 100% sure u don't have anything?"
In July 2014, we received our most persuasive intelligence to date — financial records that detailed a hush-money payment to ensure a former lover maintained silence over his HIV status.
The next month, another source came forward: Charlie's former drug dealer, who had been part of his inner circle since 2010. Not only was Charlie HIV positive, he claimed, but he had witnessed Sheen have unprotected sex with multiple partners after learning of his condition. The dealer also swore that Charlie had paid them off — not only as a "sorry" for exposing them to HIV but as inducement to keep their mouths shut.
One of them was the source's own girlfriend. And when Charlie found out she knew of his condition, he brought out his checkbook. "He bought her a house in Calabasas and put her on his payroll to keep her quiet," said the source. "Now she's married, and she and her husband are living off Charlie. There are tons of girls that get a regular check from Charlie to keep quiet."
The more we investigated, the more this pattern came into focus: Charlie was shelling out a fortune in bribes to former lovers — and terrifying the rest into silence.
Our investigation was going beyond simply an exposure of Charlie's medical status to reveal a conspiracy from the top of Hollywood down to its seediest bowels.
Each dark revelation seemed to engender another. We learned, for example, that Charlie was not only friends with a convicted child sex offender but that he was paying him as a "dialogue coach" on his FX comedy Anger Management. When the producers discovered the man's past and tried to sack him, Charlie threatened to not work unless his friend was let back on set. The producers backed down — although they refused to have him on the payroll. By September 2014, the man was on set every day, his salary covered by Sheen.
Another informant confirmed what other sources had told me: Sheen had contracted HIV from a transsexual lover in 2011 and continued to have unprotected sex. "Charlie doesn't give a fuck if he lives or dies," he said. (Sheen insists that he doesn't know how he contracted the virus.)
A close friend — famous in his own right and a pal of the star's for two decades — shared a letter with me he'd written to Sheen in which he begged him to go public, claiming that Magic Johnson (who announced his own HIV status in 1991) would sit with him in the press conference. "I know with 100% certainty," he wrote to Charlie, "that as long as you are in control of how the message is delivered, there is no way possible this could do anything but help you from a business standpoint."
This friend also confirmed that Charlie was paying out a fortune in a desperate attempt to keep the news quiet. "I know that people are extorting him and have extorted him for hundreds and hundreds and thousands of dollars threatening to go public."
It fit the pattern. We obtained a secret file containing Charlie's financial documents that itemized expenditures for 2013, including $1.6 million on "friendly entertainment" (his euphemism for prostitutes); child-support payments to ex-wives Mueller and Richards for $55,000 a month each; and a payment of $396,000 to a mystery "Miss B."
The documents also contained details of American Express cards he had given to a number of women — each with a $15,000 limit. The papers showed that among them, the women had spent more than $42,000 in a single month.
One of the names stuck out: Megan Levant, one of Sheen's former goddesses. We published a video in which Sheen's ex-fiancee Scottine Ross states to another individual that Levant received a $1 million payoff from Charlie. She did not know why — and Levant was legally forbidden from revealing the terms of the deal.
Even more ominous than paying for silence were details of the nondisclosure agreements that emerged from Sober Valley Lodge. Charlie had legal papers drawn up that all visitors and sexual partners had to sign. It meant that they had to keep all communication (both written and verbal), personal information and details of their interaction with Sheen private or face legal ramifications. Disclosing any of this "confidential information" to friends, family, social networks, media organizations or publishers would incur a penalty of $100,000 — in addition to any money gained from breaking the agreement.
He was bullying them into silence. And worse, the NDA compelled any legal challenge to be heard not in a court of law but by a mediator — and confidentially. "We understand, acknowledge and agree that there is no right to an appeal or a review of an arbitrator's award as there would be of a judge or jury's decision," it concludes.
In real terms, this meant that anyone who wanted to accuse the star of knowingly having unprotected sex while HIV positive was muzzled before they could even seek recourse.
In April, the gossip blog Diary of a Hollywood Street King uploaded a series of posts alleging that Charlie was HIV positive and that he was paying out millions to former porn star and prostitute lovers to keep silent. The posts quickly disappeared. We obtained emails and documents from lawyers representing Sheen thanking the blog owners for their "prompt work deleting and/or redacting the offending content" — and outlining a payment schedule of $100,000 for doing so.
The same source who had showed us his letter begging Charlie to go public shared texts received from Sheen once the star had gotten wind of his intentions. A 20-year friendship is wiped out in a frenzy of insults and threats.
"Go away shit head," he wrote. "Traitor. U fukked w the wrong dood." Later: "Some losers gotta learn the hard way … watch your back. Oh and your front. Oh and both sides … Oh and hey tuff guy: my CIA nickname is not WAS Raven … why don't you tell the world that …? I'll leave it carved into your dick …"
One night at the mansion, Sheen went to bed with his goddesses and left the author to scroll through Sheen’s iPhone photos of crack pipes, naked prostitutes and a shrine to Hayden Panettiere.
He ends the rant: "ps — Gil [Sheen's head of security] sends his best. Lemme make this very clear to you young man; you are never welcome here again. Are you confused by this? Because if you are come here right now and I'll demonstrate that rule while teaching you some long overdue manners. I'm not kidding."
Such threats were common. In February 2014, Sheen had become engaged to another porn star, Brett Rossi, who'd reverted to her real name, Scottine Ross. The pair separated in October, and in November, she was hospitalized after an apparent intentional drug overdose. I documented a conversation with another of Charlie's inner circle who recounted a pattern of domestic violence.
"I would often find her hiding in guest rooms crying," he said. "The real reason she tried to commit suicide when they broke up was because she feared for her life. He threatened her while she was pregnant, stating: 'It's me or the baby. If you choose the baby I will kick you to the curb and leave you homeless with nothing.' "
He also claimed that Sheen "threw her around like a rag doll" in a drunken rage and showed me photographs of Scottine after another argument — her neck was bruised, her shirt torn. "There were many incidents when Scottine wanted to run," he said, "but she feared for her life."
A former employee of Sheen's corroborated the violence — and added a chilling dimension: "One night, Charlie and I were talking about guns. He said, 'I bet you don't own guns like I own guns.' "
He went on to describe how Sheen had displayed a Lapua .338 sniper rifle with a high-magnification scope and a range of nearly 2,000 yards. "It came out of a large safe that was full of long weapons," he said. "Rifles and assault rifles, security-type guns. Some handguns in there."
He estimated there to be 15 weapons in Charlie's possession, "not including each of the security guys carrying Glock 40s."
"He's unhinged," concluded our source.
"He threatened to kill me. I know he threatened to kill Denise [Richards]. He just calls her and tells her, 'I'm going to kill you.' Basically, when he's not getting his way that seems to be the M.O.: Threaten to kill you."
And now, in the midst of it all, that phone call, with Charlie threatening me. Whatever relationship we had was over. "I fucking dare you," he yelled. "Now it's a challenge. I fucking dare you."
We had some extraordinary detail. Former goddess Bree Olson told us how he used lambskin condoms — which protect against pregnancy but are next to useless as far as sexually transmitted diseases are concerned. And transsexual porn star Meghan Chavalier revealed that she and several friends had been hired by Charlie as long ago as 1997 — their orgy had culminated with Sheen performing oral sex on one of the participant's boyfriends. Another transsexual told us how he had paid her $20,000 for sex.
We had photos of his sex den — complete with a startling array of toys — and testimony from a Hollywood madam who claimed he did not inform her clients of his HIV status.
We had details of many of his hush-money pay-outs — including $1.5 million to two twin-brother male escorts with whom he had slept after his diagnosis in an encounter that was videotaped. I personally watched another same-sex act caught on tape — Sheen had shelled out millions of dollars in another secret settlement after the subject of that tape claimed the star had given him herpes, despite claiming he was "clean."
As is customary, we informed Sheen's reps that we intended to run the story — based on our evidence as well as information provided by at least five sources.
Their response was typically bullish. Our information was false, they said: Charlie had, in fact, had a medical exam, including a sophisticated state-of-the-art blood test, which proved all our allegations wrong. What's more, over the course of a five-page letter from his legal team, I was threatened with a major-league lawsuit and "astronomical punitive damages" if we published what they called "defamatory lies."
I seemed "hell bent on being sued," they wrote. "If AMI [the Enquirer's parent company] wants to get sued and face the risk with this despicable story, so be it. If this story is published, everyone should be prepared for the $100 million dollar lawsuit to come."
We backed down temporarily, determined to bolster our sourcing even further. The next 11 months were nail-biting. My relationship with Charlie was shot irreparably, and every story we posted provoked another tantrum. We ran them anyway. In March 2015 we revealed his assaults on Scottine, and through the summer and fall uncovered seven more sources, along with video, email, photos and text messages confirming Sheen's HIV status — and, more importantly, the scale of his efforts to keep it secret.
In 2011, the author was invited by Sheen to observe him taking blood and urine tests to detect marijuana, cocaine, opiates, amphetamines and alcohol, but the results were all negative.
We were ready to publish the big one. And this time, we weren't going to back down.
Over two and a half years, we had assembled thousands of legal documents, sworn statements, text messages, photographs. We were watertight.
To get the ball rolling, we pulled an old tabloid trick — running a "blind item" in October 2015 about "a bad boy Tinseltown star" whose "explosive secret" is that he's HIV positive. It worked. More individuals came forward … and I took a phone call from a member of Charlie's team asking if we intended to publish his name. My response: Why, if he was not the man in question, were they even calling to ask?
The pressure built, and even as Scottine agreed to settle with Sheen for $1 million to "maintain confidentiality" (the actor later rescinded the offer; negotiations are ongoing), we told Charlie's camp that we were going to print our story soon. We had Scottine on video burning photographs of her and Charlie together: "You exposed me to HIV for a year and a half!" she screams.
This was Nov. 11. The next day, Charlie's people began discussions with NBC about an interview. The following Monday, Matt Lauer and Today tweeted that Charlie would appear the next day to make a "personal announcement." This was it. He was attempting to limit the damage — to be, in the words of his former friend, "in control of how the message is delivered."
Within minutes, we published our story online. Subsequent issues of the National Enquirer revealed for the first time, and in exhaustive detail, the extent of Sheen's debauchery — and the spectacular arc of his flameout. We went to town on it. And every word was true.
After our story, he chose to sit down with me for a one-on-one interview. "I am in a rare position to turn my diagnosis into a positive, and that began with telling the truth," he claimed. Charlie has been more concerned with damage mitigation than telling the truth about his diagnosis.
At the same time, revelations keep coming: Worried ex-lovers are lining up to declare that he knew he was HIV positive when he slept with them. I'm aware of seven victims who've retained legal counsel since our first report.
Medical tests are being re-examined. Even the drug tests he took with me for RadarOnline in 2011 are now in doubt: Questions have been raised about whether Sheen cheated them by using a "Whizzinator" (a "synthetic urine device" used to thwart such tests) and having a blood transfusion to ensure we extracted drug-free blood.
In the months since publication, I've had to employ personal security. Many times, I've been told that Charlie doesn't make idle threats; and if ever a man had motive and means, it's him.
On Nov. 23, after the Enquirer's second week of biting revelations, I received a phone call from one of Sheen's closest confidants, who told me: "If I were Charlie, I would come after you and kill you. … If you did to me what you did to Charlie, I would have had you killed by now."
So why did we publish? The answer couldn't be simpler: Because it was the truth. Entertainment journalism can get a bad rap, but in this case, the right to privacy of one individual was far outweighed by the risk to those who did not know about his HIV status.
Details of the cover-up continue to surface. Late in March I received an audiotape of conversations recorded by an ex-lover during which Charlie admits not only having unprotected sex without first revealing his HIV status, but also that he outright lied to his partner — telling her he was not infected by the virus. His reason? "Because it's none of your fucking business, OK?"
The actor, with “goddesses” Olson (left) and Kenly in 2011. (Photo: Jean Baptiste Lacroix/Wireimage)
He also claims of ex-fiancee Ross, "I can't be fucking extorted.
"This piece of shit needs to be fucking buried ... you get it," Sheen told the ex-lover after Ross sued him for assault and battery and HIV exposure. "It's called treason. You know what treason is? It's punishable by death."
"What are you going to do?" she replied.
Sheen didn't mince words: "I'd rather spend 20 grand to have her head kicked in. Then people will realize, 'Oh, it's dangerous.' "
The tape not only contradicts his so-called confessions to Matt Lauer, Dr. Oz and others, but also raise questions about whether Sheen may have violated California law; a state health and safety code makes it a misdemeanor to "willfully expose yourself to another person if you are afflicted with a disease that is contagious, infectious or communicable."
After the Enquirer published this latest scandal, Scottine contacted the Los Angeles Police Department and successfully filed a restraining order against the star.
The story of my chase with Charlie is a glimpse into the dark heart of the American showbiz dream. It's about how the system not only facilitates the horror but perpetuates it. It's a story of power, corruption and lies unprecedented in Hollywood history. And I have no doubt that there's more to come.
I'll be there when it does.
A rep for Sheen responds: "It's unfortunate that Dylan Howard has such anger toward Charlie, which, ironically, was caused by the anger that Charlie's ex-fiance Brett Rossi took out on Dylan over the stories Dylan's publications were writing about her."
Sheen (right) revealed his diagnosis to Lauer on Nov. 17, 2015. (Photo: Peter Kramer/NBC)