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Hollywood’s Most Toxic Bromance: The Implosion of Charlie Sheen and Lenny Dykstra

He's a former major leaguer nicknamed "Nails" and an ex-con hustler who made (and lost) millions, but none of that could have prepared Dykstra for his friendship with the wild-man actor, who he alleges is a dangerous criminal about to be taken down by the Feds.

Lenny Dykstra, the ex-con and former major league center fielder, relishes his wild-man reputation, and relishes running his mouth about it even more. With roughly Pete Rose’s chance of making it to Cooperstown, he’ll talk about gobbling Human Growth Hormone with his cereal during his playing days just as easily as he’ll open up about how, in his mid-50s, he’s developed a post-prison side gig as a silver-haired gigolo to Beverly Hills grandmothers.

But over lunch in a corner booth at The Beverly Hills Hotel’s Polo Lounge, it’s another wild man, more famous and even more hard living, once his best buddy but with whom he no longer speaks, who has him gabbing. Dykstra explains that he believes his onetime friend Charlie Sheen is on the verge of being prosecuted, in a roundabout way, for knowingly spreading his HIV — and that the actor is under federal investigation for tax and wire fraud. What’s more, Dykstra claims to know this because it was his own semi-accidental whistle-blowing to the government that got the Internal Revenue Service sniffing around in the first place. “I don’t know why Charlie doesn’t try to leave the country,” he says.

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Dykstra, 54, nicknamed “Nails” decades ago for his relentlessness on the field — parts of five seasons with the New York Mets and eight with the Philadelphia Phillies — isn’t done. He goes on to float that Sheen was involved in the sudden death of a member of his own inner circle and beat his pregnant ex-fiancee. The 52-year-old Sheen, says Dykstra, is not simply the drug-addled clown the tabloids have been feasting on for years but is truly dangerous.

Dykstra is going public now with this new info about Sheen, he says, because he’s genuinely sickened by the worst of the actor’s behavior. “I am not a saint, but I will not tolerate a man beating a woman,” he says. Still, under questioning, another motive emerges.

Dykstra was friendly with Sheen for more than two decades, eventually joining his core clique. Now he’s excommunicated. His allegations against Sheen are telling; his willingness to share them even more so. The doomed bromance of Lenny and Charlie is a glimpse into the hedonistic lure of a real-life Entourage, only sadder, more desperate and ultimately damned — a cautionary tale about Hollywood alpha-male bonding at its most decadent and damaging.

The industry has always been a magnet for guys like Dykstra: confident outsider-hustlers who see opportunity in its chaos, imagining that their accomplishments in other fields mean they must have the wits, guts and guile to conquer the gilded mayhem. But with Sheen and his all-star team of professional handlers, Nails met his match.

Like his ex-pal, Dykstra has a public reputation so sullied that Newsweek referred to him as a “scumbag” after he had a Twitter dustup with Lena Dunham. Yet Nails, who speaks with a lisp due to a jailhouse beating that left him with many missing teeth, is self-aware enough of his notoriety (and so eager to instill confidence in his tale) that he insists on providing the password to his personal email account for full disclosure. “Look at whatever you want,” he says. “I’ve got nothing to hide.”

Press Dykstra about his rationalization for selling out his former friend, and he’ll tell you that Sheen took his wise counsel for granted, ignored it and left him with nothing to show for it. No surprise, Dykstra is hoping to drum up interest in a possible stand-alone Sheen documentary project as well as a multipart docuseries about his own over-the-top life — he envisions it in the sweeping, kaleidoscopic terms of O.J.: Made in America. “There are so many people to interview, from prison guards to my [private plane] pilots to pussy,” he says.

If Dykstra’s actions mean Sheen gets burned, so be it. “Charlie is getting what he deserves,” he says. Sheen declined to speak for this story. But Dykstra doesn’t appear at all conflicted about publicly crossing his ex-friend, even one who once warned him to “watch your front side, watch your backside, watch both sides.” Dykstra takes a swig of Irish coffee, settles into his booth and alludes to his time at the federal penitentiary in Victorville, California. “When you’ve been where I’ve been, I’m not afraid of anything.”

The bad-boy pair first hung out when Dykstra’s Phillies were in Los Angeles playing the Dodgers during the 1993 season. Sheen — who dreamed of being a big leaguer as a kid and was then reprising his role as reliever Rick “Wild Thing” Vaughn for Major League II — cold called him at the clubhouse with an invitation to his Malibu home. “I was a huge fan of Wall Street,” says Dykstra. “Turns out he’s a serious baseball guy: He has a cage lit up like a pro stadium. I told him, ‘Dude, you can hit!’ He could.”

That first evening, Sheen uncorked a $3,000 bottle of red wine (“I spilled half”) and then, once “hammered,” showed off what Dykstra describes as his “legitimate fucking gunnery” and suggested they fire off automatic weapons together. Dykstra passed, but the two became buddies. “He’s funny, he’s smart, he knows about everything,” says Dykstra.

Dykstra, who last played in the majors in 1996, retired at age 33 to a notoriously checkered business career. He was involved in car-wash dealerships, quick-lube centers, jet charters and stock picking. By 2008, he was worth $58 million. The following year, he had filed for Chapter 11 and was reportedly forced to sell his Mets 1986 World Series ring to help pay off more than $31 million in debt.

His problems weren’t merely financial. Between 2009 and 2011, Dykstra was accused by a former employee of making racist and homophobic remarks, writing a bad check to an escort and sexually assaulting his housekeeper. He also was charged with indecent exposure, drug possession, grand theft auto, identity theft and filing false financial statements — and eventually sentenced to three years.

Before going to prison, Dykstra reconnected with Sheen in February 2011 after having lost touch for some time. Fittingly, they ran into each other at the UCLA baseball field, as Dykstra helped his son Cutter, then a minor league player (and husband of Sopranos actress Jamie-Lynn Sigler), practice for the upcoming season. “Charlie came running up to me, hugging me, telling me how much he missed me,” explains Dykstra. “I could tell he was lit up but in good spirits.”

Over just a few frenzied months that spring, before being taken into custody in June, Dykstra found himself operating as a Thomas Cromwell-style fixer in the erratic Beverly Hills court of King Charles. When the actor ended up in an embarrassing cash crunch while attempting to purchase film producer Mike Medavoy’s Mulholland Estate house for nearly $7 million, Dykstra claims to have secured a hard-money lender at the last minute. After Sheen went on Alex Jones’ Infowars radio show and disparaged his Two and a Half Men showrunner Chuck Lorre as “Chaim Levine,” Dykstra begged him to apologize. Sheen didn’t, and Warner Bros. Television fired him soon after.

Despite his best intentions, Dykstra says most of his efforts to act as the star’s unofficial manager were met with resistance. He says Sheen, despite his urging, snubbed a $2 million cameo on the Australian iteration of Big Brother and could not be persuaded to perform his infamous “Violent Torpedo of Truth/Defeat Is Not an Option” speaking spectacle as a Las Vegas residency. “He turns it down to go play a bunch of fucking rinky-dink cities. It was crazy.”

Dykstra also cooked up a series of licensing deals, including a vaping product called Nico-Sheen and a caffeinated liquor, Sheen Vodka, which were to be hawked on an umbrella web portal titled Planet Sheen. He says that Sheen’s personal manager at the time, Mark Burg, and former business manager, Barry Klarberg, kiboshed the whole thing.

“Lenny was a friend of Charlie’s who tried to get more involved in his life, and I don’t think he ever wanted that,” explains Burg. Klarberg did not respond to requests for comment.

In a March 21 email to Dykstra reviewed by THR, the actor pulled the plug on Planet Sheen: “The pressure I’m under from my business team to NOT pursue this with you, is tsunami-esque.”

Dykstra’s tussles with Sheen’s circle continued after he returned from serving out his three-year stint. He asserts that Burg, Klarberg and Sheen’s then-attorney Marty Singer put the brakes on Dykstra’s most audacious gambit of all: a complex $85 million play to sell the note on what remained of the actor’s Warner Bros. financial package to solve Sheen’s cash crunch. He insists it was sabotaged late in the game when they realized what the document-review process might expose. Before he could bring anyone in on the details, “Marty put an NDA together that was so vicious, so stacked, that no one would sign it,” explains Dykstra, still fuming. “I finally get one [potential investor] to sign it and what do they send him? Dick. Nothing relevant.”

Singer disputes the claim as “absurd and ridiculous. The NDAs were appropriate,” adding, “As far as I understand it, Lenny likely had an NDA, too, and I don’t believe he’s living up to it.” Dykstra responds that he doesn’t “give a shit” about breaking its terms “because I was saving Charlie’s fucking life.”

All of this time, Sheen’s drug use was worsening. During the manically loquacious interview spree in early 2011 that bequeathed pop culture the catchphrase “Winning!” Dykstra claims the actor was high on OxyContin: “When [the pills] are at their peak, it’s a euphoria, where you’re smart and you’re creative and you’re quick and you’re invincible.” But by summer 2014, Sheen had locked himself in a crack den hidden in his mansion for nine days. “It was right out of a mystery spy thriller, with a sliding bookcase,” says Dykstra. “I walked in and Charlie was standing there with a glass dick — a crack pipe — in one hand and his phone in the other. I took one look around, there’s all this stuff, cool paintings and Babe Ruth’s ring, and I said, ‘Charlie, I have to admit, if you’re going to smoke crack, this has got to be the best crack den on the planet!’ That broke the ice.”

By Dykstra’s account, Sheen soon confessed to him that he had HIV, which he believed he’d contracted from a transsexual partner, and that he was being extorted for millions over the secret. Dykstra urged the star to go public about his health, as Sheen’s parents, Martin and Janet, had already been urging. “I said, ‘You can’t live like this anymore — this isn’t even living.”

Dykstra contends that he was crushed by Sheen’s last-minute decision to pull out of a news conference he’d helped arrange that November for his friend to get out in front of the diagnosis — a full year before the National Enquirer would finally force the issue. It was to be held at Sheen’s parents’ house, with Hollywood publicist Larry Winokur brought in by Dykstra to orchestrate the crisis management. Winokur, whose casting-director wife had hired Sheen on Major League and Lucas, confirms Dykstra and Sheen reached out to him about the plan, noting the sincerity with which Dykstra approached the endeavor. “Lenny played team sports very successfully, and if you’re on Lenny’s team, I think he’d give you the shirt off his back,” he says.

By the end of that year, Dykstra had come to believe Sheen was suicidal. Dykstra was reduced to attempting to rein in his buddy via desperate, all-caps-laden text messages. “Charlie, you are a fucking winner!” Dykstra typed during an exchange on the evening of Dec. 21. “Do not quit on me bro! I KNOW YOU ARE NOT A PUSSY!” Sheen replied, “I’m too tired bro going away now where no one can hurt me ever again fuk tv fuk media fuk the public fuk cutting deals fuk getting rolled I own my truth forever adios senior….. x”

Dykstra appears most solemn when discussing the summer 2012 death of Rick Calamaro, Sheen’s recently fired assistant, as well as the alleged violence perpetrated against Sheen’s ex-fiancee, Scottine “Brett” Rossi.

L.A. native Calamaro — known for his years as the phone-glued-to-his-ear partner at A-list velvet rope clubs like Holly’s and Ivar — was discovered July 1 by his maid, lying face up in his bed beside a bottle of Jack Daniel’s, in his longtime Fairfax district apartment. The autopsy report listed “very high” levels of Fentanyl, the powerful opioid, and noted that Calamaro, 50, had suffered from depression and had been taking a mixture of prescription medication for pain and anxiety. “Based on the history and circumstances, as currently known,” the autopsy concluded, “the manner of death is accident.”

Calamaro extended his gatekeeping instinct at times to Sheen’s social circle, eventually earning the enmity of Dykstra, who grew convinced that Calamaro was working on a tell-all. “Before I went [to jail], I said, ‘Dude, this guy, he is writing a fucking book, you got to fire him,'” recalls Dykstra (while freely admitting he himself later served as an unnamed source for the Enquirer).

After he got out of jail, says Dykstra, he asked Sheen, “What the fuck happened to Calamaro?” who had overdosed while Dykstra was in prison. “He said, ‘You mean Dead Rick? What fucking happened is the motherfucker tried to blackmail me just like you said — wanted $5 million. I had him fucking iced.’ He said he had a hot dose put in there,” using slang for a lethal intravenous injection prepared for an unsuspecting victim. (Dykstra again offers no proof his recollection is accurate, and Sheen’s current lawyer, Shane Bernard, issued a denial of the allegations, noting Dykstra’s “laundry list of crimes” and asserting that his “disturbing, vile and outright ridiculous claims” are unreliable.)

Sheen’s close friend, Tony Todd, who lived with the actor during this period and has known him since the two attended Santa Monica High School, laughingly scoffs at the charge, adding that even if Sheen were to have done such a thing, “Charlie’s not going to tell it to Lenny Dykstra!

Rossi says that while she is unaware of such an admission pertaining to Calamaro specifically, it’s certainly possible given her own history with the actor, which she outlined in a 2015 lawsuit. According to her filing, Sheen said “he wanted to murder people that he was angry with.” The suit also refers to a “hit” Sheen allegedly took out on Rossi’s ex-husband. The following year, she obtained a restraining order against Sheen after the LAPD began investigating an alleged recording in which he threatened to pay someone $20,000 to “kick her head in.”

Since Sheen himself won’t comment, the likelihood of another scenario — that the star, while high, simply made a distasteful joke about having Calamaro killed — is unclear.

Dykstra has a complicated relationship with Rossi, a porn star who says she met Sheen on a $10,000 escort date. Early on, as a favor to Sheen, Dykstra hired “an Armenian buddy to follow [Rossi] for a few days” to confirm she wasn’t cheating on him. (Dykstra says he used to hire private eyes to dig up dirt on umpires, noting “it wasn’t a coincidence” that he led the league in walks in 1993.) Dykstra eventually became Rossi’s confidant, and she divulged details of Sheen’s sexual kinks. Rossi tells THR: “He would look at transsexual porn when he was high and [ask her], ‘Which one is hot?'”

Dykstra claims to have seen further proof of Sheen’s lifestyle. He says that attorney Keith Davidson, recently in the news for orchestrating porn actress Stormy Daniels’ alleged $130,000 payment to stay quiet about a 2006 affair with President Trump, showed him a copy of the tape that media outlets have reported was circulating in which Sheen participated in gay sex. (Over email, Davidson asserts, “This just never happened.”)

Rossi confirms that once Sheen kicked her out, it was Dykstra who helped her free up money by selling off her pricey gifted watch collection to underground buyers and listened as she told stories of domestic abuse by Sheen, including battery, false imprisonment and that he knowingly exposed her to HIV (all of which she alleged in a December 2013 lawsuit). Rossi told Dykstra and confirmed to THR that Sheen, concerned over how his crack use would affect the fetus, pressured her to get an abortion. “Right now,” says Rossi, “I would have a 3-year-old running around.”

Dykstra shakes his head in repudiation. He is bothered less by the possibility of Sheen’s involvement in Calamaro’s death than what allegedly happened to Rossi. “Killing the guy that fucking tried to extort him: That’s his business,” he says. But what Rossi alleges happened to her is too much for him. “Men, they get in rages. But no pummeling.”

Dykstra’s evident frustration with how things always seemed to go for him when it came to Sheen — sideways, to his mind, with him playing the good guy but getting no recognition to show for it — reaches a crescendo as he recalls another grim episode involving Rossi in November 2014. As he has it, she dialed him in tears, having overdosed on Valium in her Encino home, which she’d moved into after her breakup with Sheen.

Scottine says, ‘I’m dying.’ I say, ‘There’s a number for that: 9-1-1.’ ‘No, Charlie won’t like that.’ I go over there, she says she needs to go to the bathroom. It hits me. I run in and she’s swallowing a handful of pills. I tackle her and they go all over, but she gets a lot down.” Dykstra is an often-demonstrative raconteur, acting out the maneuver. “It was out of Pulp Fiction. Soon I have her in my car, driving to Cedars, flying down the 405, shaking her: ‘Don’t fucking die on me, bitch!'” He pauses, shakes his head. “I was on probation, dude!”

He’s still irritated that “no one knows I saved her life.” Worse, he adds, getting worked up, Rossi never acknowledged his heroism. “The amount of times she thanked me is zero. Can you believe it?”

Rossi confirms the pill incident but says that Dykstra — whose ditching of her at the hospital was so abrupt, she was forced to submit to a rape kit (“That’s what happens when some guy just drops you off and goes, ‘Bye!‘”) — should be gallant enough not to ask to be recognized as her “knight in shining armor.” She laughs. “He’s still talking about that?”

Dykstra began to lose favor in the court of King Charles — all of those gone-nowhere deals, all of that advice not taken. And what he considered his one, momentarily satisfying victory was, in hindsight, the thing he’s sure will be Sheen’s ultimate demise.

Dykstra long suspected that another mansion nemesis, Sheen’s head of security, was ripping off the boss — charging personal expenses, including getaways and real estate taxes, back to Sheen. And he believes he has the AmEx bills (shared with THR) to back it up. The military veteran insists zero embezzlement took place and that any and all charges “were made with Charlie’s permission.”

In any case, it wasn’t any purported theft that led to the employee’s firing. “What did it is that Charlie went to check his guns,” recalls Dykstra. “He calls me drunk, freaking out: ‘He took the fucking pins outta my guns! He put my family in danger!’ He went the most nuclear I’ve ever seen him.” Dykstra laughs, observing that in spite of his feelings about the security chief, “I would’ve taken those pins out too, the way Charlie was [behaving].”

Still, Dykstra worried that the terminated employee would seek retribution and sought to neutralize him. Given Dykstra’s probationary status, he figured his best bet would be to pass on documents that he believed incriminated the man to the IRS. On Oct. 8, Dykstra got an email from an IRS agent, asking for a follow-up call. But the investigator wasn’t interested in talking more about the security chief. He had turned his attention to Sheen. “[The IRS agent] says, ‘What do you know about these $20,000 cash payments for “women of the night”?’ That’s when I knew they’re going to come at him with tax fraud, wire fraud — everything.” (The IRS will not comment on particular tax cases.) Dykstra knows from experience what it’s like when the government, patient and powerful, zeroes in on you. “It was a felony if you didn’t tell a woman you have HIV when you know it. Nothing has happened to him since all of those women went public. Think about it,” he says, proffering his own legal analysis. “This is how he is going to go down.”

Dykstra and Sheen haven’t spoken since Dec. 21, 2014 — a final two-hour call initiated by the actor, whom Dykstra characterizes as downbeat. “He kept on saying how sorry he was,” he recalls. “Charlie said, ‘Everything you told me was right, they all lied to me.'”

Dykstra believes that although they reconciled during the conversation, Sheen couldn’t bring himself to ever hang out with his old buddy again, since during a heated argument weeks earlier, Dykstra had revealed he had seen Sheen’s allegedly compromising sex tapes. “He couldn’t face me. He knows what I saw. He’s humiliated.”

Yet livid texts sent by Sheen to Dykstra on Sept. 9 and obtained by THR from another source point to betrayal, not shame, as the actor’s reason for cutting off his friend. Sheen discovered that Dykstra planned to pocket 5 percent of that Warner Bros. payout deal — a cut the star felt had been arranged behind his back. Sheen typed: “bro – I repeatedly asked you, (and DO NOT CHALLENGE MY MEMORY) ‘Hey Len, what’s in this for you?’ and you always said; QUOTE: ‘Oh hey man, we’ll figure out something fair later on …’ well now I have to re invent what later on means between us. Newsflash GasLighter; You FUCKING KNEW FROM JUMP STREET WHAT IT WAS … you came in here to clean house and also clean my HARD EARNED CLOCK!”

More than anything, Dykstra wants to present himself as the ultimate cleanup hitter, an unsung hero (OK, antihero) who in selfless service of a buddy went up against Hollywood’s most sordid retinue. He can’t countenance the prospect that he might not have been trustworthy, that maybe he was just out to extract his piece like all the rest of them.

Or perhaps his initial motive for joining Sheen’s team truly was as simple as friendship. This just wasn’t his sport.

Following that final call on Dec. 21, 2014, Dykstra texted Sheen once more. “It makes me feel so good that you know ‘I AM WHO I AM’ and the fact that you know I am your REAL FRIEND!” And continued, “FYI — I deleted everything on this phone and nobody knows we spoke tonight.”

His signoff: “NAILS OUT!”

This story first appeared in the Feb. 7 issue of The Hollywood Reporter magazine. To receive the magazine, click here to subscribe.