With a pair of Gucci glasses clutched in his hands, Milo Yiannopoulos sits behind the Resolute Desk—the same desk behind which President Trump and six past presidents have sat in the Oval Office—preparing for war.

“My whole day, from when I wake up to when I go to bed, consists of warring with people,” he tells me. “Bullying them and humiliating them into doing the right thing.”

This isn’t the White House, of course, and Milo’s Resolute Desk is merely a mahogany replica of the original one. I’ve joined him in Miami inside a nearly 5,000-square-foot compound he claims once belonged to a cocaine dealer and which he’s dubbed “The Meme Mansion.” Painted across the walls in black letters, opposite a gigantic American flag draped behind him, is one of Milo’s favorite zingers: “Feminism Is Cancer.”

Months after Milo publicly self-immolated in a scandal that saw him resign from Breitbart News and have a major publisher cancel the contract for his contentious memoir, the self-styled “Dangerous Faggot” is plotting his revenge in the form of MILO Inc, a young conservative propaganda machine built around his personal brand of bomb-throwing nihilism, which he’s staffed with a group of twentysomethings who loyally do his bidding.

Bouncing anxiously behind his desk, Milo rifles through a row of prescription pill bottles. He shakes each one like a tiny amber maraca, pouring pills into his palms and examining them for familiarity, in search of something to bring him down a notch. Even though the mansion is kept on the frigid fringes of 52-degrees Fahrenheit, he’s swinging back and forth as if plagued by spiking body heat, glasses on, glasses off, each time whipping out his iPhone and holding it up to his face like a compact mirror. Like a zit on his tanned and moisture-rich mug, I’m just a thing Milo has to deal with today—a distraction from the improv of three slackers who think he’s their first-class ticket to paradise. He’s editing a script larded with their jokes for a video he describes as “Buzzfeed for conservatives.”

“Make fun of suicide rates,” he tells them. “Make fun of liberal hypocrisy. Make fun of—” He looks down at his notes. “You know,” he pauses, gently enough to make them feel insufficient, in constant need of his guidance, but never worthless. “You’re all funnier than this.”

Later, one of his writers shares a one-liner he’s prepared for one of Milo’s speeches, one he suspects his boss will reject: “Every time you Tweet a video of Trump beating up CNN, Don Lemon contracts AIDS.”

The writer admits sheepishly, “It’s a stupid joke.”


It’s July 26 and Donald Trump has just announced his intention to ban transgender people from serving in the US military, resulting in a deafening outcry in the press.

Milo’s first move when Trump makes headlines is to hijack them. When the Washington Post’s David Weigel calls him up for a quote on the trans ban, Milo provides a predictably outrageous take: “You don’t help mentally ill trans people by sticking them on the front lines. You help them with therapy and drugs—though not, I have to stress, transition surgery. I only wish he’d gone further and banned women from combat units too, since the evidence clearly shows their presence is disastrous for both morale and performance. Baby steps?”

It’s dangerous to quote me now, because you’ll be accused of botching a story. That is power.

Milo clearly takes great pleasure in sneaking his callous messaging into mainstream news sources. “You see, it’s dangerous to quote me now, because you’ll be accused of botching a story,” he says. “That is power.”

He pauses to take a call from his attorney Stephen B. Meister, who is pursuing a $10 million dollar lawsuit against publisher Simon & Schuster on Milo’s behalf. Last December, the publisher’s conservative imprint, Threshold Editions, agreed to publish Milo’s memoir in a $250,000 deal—a move that outraged many on the left, including feminist author Roxane Gay, who subsequently refused to publish her book with Simon & Schuster.

But in February, a video came to light of Milo reflecting fondly on the “incredibly life-affirming, important, shaping relationships are between younger boys and older men.” He went on to say that he was “grateful” for being sexually abused by a clergyman as a teen, adding wryly, “I wouldn’t give nearly such good head if it wasn’t for him.”

The denunciations came swiftly from both the left and the right, with critics accusing him of condoning pedophilia. In the wake of the scandal, Milo resigned from his position as tech editor at Breitbart, was disinvited from a speaking engagement at CPAC, and saw Simon & Schuster immediately cancel the book deal.

Milo and his attorney contend that the contract was broken in bad faith; that the publisher balked under the pressure from authors, journalists and an avalanche of hate mail. Nevertheless, Milo kept the $80,000 advance, which he spent, he nonchalantly claims, on designer shoes.

“Every penny,” he says.


By the end of February, Stephen Bannon—the former and now current executive chairman of Breitbart, and the man who provided Milo the soapbox he needed to attain the zenith of his fame and influence—was consolidating his power in the White House, with many in the media floating the words “President Bannon” and suggesting that he was the puppetmaster manipulating Trump’s strings.

But Milo was seemingly at his nadir, abandoned by many former supporters on the right and apparently vanquished by his critics on the left. Not one to slink off into the shadows, however, he decided to spend the next two months planning his revenge.

His secret weapon: MILO Inc., a full-scale media company that will be “dedicated to the destruction of political correctness,” according to a press release. At first blush, the site looks little different than that of any other media startup. Users can sign up for Milo’s newsletter or purchase copies of Dangerous, which Milo self-published in July, and other Milo merch. But the site is ultimately designed to convert his followers into “mini-Milos,” vicious little heirs to his caustic throne. “Eventually, there will be 5,000 people waiting to take my place if I die,” Milo tells me.

As part of his master plan, Milo states that he’s developing himself into a “conservative-leaning Bill Maher,” in order to present conservatives with a show that he feels they need, something Fox News—which won’t touch Milo and the median age of which is about 70—simply can’t provide. playboy has learned through industry sources that a Milo-focused show with Amazon was pitched, but never reached the development phase. (At press time, Amazon had not yet responded to a request to confirm this.) A Heat Street employee who wished to remain anonymous confirmed that Milo was, at one point, offered a low six-figure salary for a position at the media outlet, which he did not end up taking.

Of course, he can’t embark on a project like this alone. One of his partners is Alexander Macris, MILO Inc.’s CEO, who handles the financials, legal paperwork, investor pitches—and Milo’s Hindenburg-sized ego. Macris is also Milo’s right-hand man and the only guy, other than Bannon and Breitbart editor-in-chief Alex Marlow, who can synthesize his trolling into tangible financial and philosophical terms. Macris talks about Milo as if he’s a weapon of mass destruction, or the last hope against the Borg-like army of assimilators he believes are at war with free speech and Judeo-Christian society. He’s strongly influenced by Ayn Rand and, like Milo, was liberated by reading Atlas Shrugged as a teenager. Milo describes Macris to me by saying, “I play super-villain because it’s good marketing, but he genuinely is one.”

I ask Macris how he’d describe MILO Inc. to an investor. “It’s an aspiration-entertainment-lifestyle brand with Libertarian values,” he says. “A lot of conservatives are afraid of coming out as conservative because it might hurt their economic prospects. Milo is an aspiration brand, because Milo is famous, rich and popular, and if he can do it, others can do it, too.”

According to Macris, the company currently has a staff of about 20 employees divided into four divisions, including book publishing under “Dangerous Books”; live tours with Milo and special guests; merchandise such as cheeky “Bannon 2020” T-shirts; and media, which they’ve purposefully kept small.

There appears to be another part of the business that nobody will elaborate upon nor confirm, one in which MILO Inc. has allegedly been working with right-wing street artist Sabo, who tagged UCLA in June by plastering the walls of Westwood with glossy ads for Milo’s book. Milo denies having hired Sabo to help fight his propaganda war, but admits his brand is reliant on making sure Americans cannot avoid his face—guerrilla marketing in the face of mainstream opposition.

“We expect a lot of people to attempt to roadblock us with advertising, by organizing boycotts and pressuring sponsors,” Macris says. “But they certainly can’t stop fans from opening up their wallets and supporting what they love.”

To hear Milo speak about the company, however, you wouldn’t think that he needs to rely on his fans for financial support. He claims that he was able to raise $12 million in funding within the span of 72 hours, though he would not disclose the names of his investors. playboy can confirm it is a sole investor, through an LLC, behind the $12 million.

This is where things get muddy, however. A source close to MILO Inc. says the startup only raised about $2 million, which I’m told was the choice of the investor, and that $500,000 came from a woman named “Rebekah.” One might infer that’s Rebekah Mercer, the daughter of billionaire Robert Mercer and generous supporter of both Breitbart and Trump’s presidential campaign. (Rebekah Mercer did not respond to repeated requests for comment. The above-mentioned source, however, linked the Mercer-backed production company Glittering Steel to the initial funding of MILO Inc.) Rebekah Mercer is reportedly a big fan of Milo’s, and her family has donated a staggering $77 million to conservative causes between 2008 and 2016. BuzzFeed reported in July on leaked documents that strongly suggest that the Mercers are, in fact, Milo’s patrons. The same source who linked the $500,000 to “Rebekah,” however, claims the publicity-shy family would only use offshore accounts to back Milo, whose very name is cause for cataclysmic blowback that no risk-averse investor would bear.

With whatever cash injection it did actually receive, MILO Inc. is also invested in expanding its digital real estate holdings. It purchased domains such as Dangerous.com and Hatred.com, which redirect to the Amazon page for Dangerous, for sums as high as $150,000 each.

Macris tells me the company was originally going be a spinoff of Breitbart, but in order to secure Milo’s O1-Visa and avoid having him deported to England, he needed to accelerate plans to launch the company and immediately hire Milo as an employee. Both MILO Inc. and MILO Entertainment Inc.—through which Milo, Macris, and all other MILO Inc. staffers are employed—are subsidiaries of MILO Worldwide LLC, which is where investments are received. Macris’ prime directive is to help make MILO Inc. profitable, which is a difficult thing to do when your founder styles himself like a hip-hop mogul.

In fact, a source closely acquainted with Milo Inc’s inner workings says that one point, during Milo’s visit to Texas to be interviewed by Alex Jones in August, MILO Inc. was running low on money. “Milo had to personally bankroll everything during that trip,” the source says. Yet Milo isn’t curtailing his spending, including an allegedly six-figure annual wardrobe budget. As part of his preparation to dip back into the mainstream again, Milo has been going through an absurd makeover: He had liposuction on his stomach in July to look thinner, which cost him $28,000. He then squeezed bits of the excess fat into his glutes. In August, he had $65,000 veneers implanted into his jaw and his gums reconstructed, all of which, Macris tells me, were paid for by the company. Milo’s also changing his aesthetic, going from self-proclaimed “wigger to goth”; he plans to color his hair powdered white and look more like a modern vampire than mid-aughts club kid.
The makeover was paid for with money tied to MILO Inc. as a part of his hyper-patriotic persona, in which he combines jingoism with couture, including posting photos of himself holding an AR-15 machine gun with a Louis Vuitton handbag hanging from his arm. Sitting behind his desk, Milo pulls up his bank account summaries, which include countless charges: $500 or more from Balmain, Chanel, and Burberry. Milo even bought his fiancé a Tesla he had painted in a gaudy reflective gold paint, like the metal trimmings of the Trump Tower.

“If Milo lived like a monk, that predisposes him to the cliche that being conservative isn’t fun and that it’s old-fashioned,” Macris says. “MILO Inc. shows that it’s entirely possible to be cool or sexy and be right-wing.”


Like Milo’s profligate spending, his contrarian-asshole persona is both integral to his brand and a potential Achilles’ heel. In the wake of the scandal in February, Milo is keenly aware that his provocateur antics, like the racist campaign of harassment he initiated against Ghostbusters star Leslie Jones that resulted in him getting banned from Twitter, could backfire and hurt his company.

One failsafe to keep Milo from nuking his brand is a sort of in-house parental advisory commission, in the form of advisors he refers to as his “evil wizards.” This includes Stephen Bannon, whom Milo refers to as “Uncle Steve,” and Macris—a.k.a. “Dad.”

All I ever wanted was some parental oversight. My family was shit, so I invented a new one.

“All I ever wanted was some parental oversight,” he says. “My family was shit, so I invented a new one.”

Milo’s also made his fair share of enemies. The anonymous investors funding MILO Inc. apparently view him as risky merchandise who’s one public appearance away from being offed, and allegedly insisted he take an expensive life insurance policy through a Lloyd’s of London affiliate. “A portion of the company’s value is contingent on me being alive,” he says, noting that he’s also invested in a $20,000-per-month private security detail that includes ex-Delta Force, Navy SEALs and Marine Corps Force Recon. (This is out of his salary, which he claims is close to $1 million per year.)

And then, of course, there’s Milo’s legendary appetite for partying. Sources tell me that Milo had gotten so bad on the “Dangerous Faggot” tour, during which hotel rooms were allegedly trashed, that an intervention was staged in Alaska after Milo began to miss media appearances and showed up late to speeches.

But Milo tells me accusations of drug abuse are nonsense, emphatically denying any drug use—except for those pill bottles, which he says are legally prescribed. Recently, Milo posted (and then promptly took down) a photo on Instagram depicting an iced bottle of Dom Perignon next to a row of prescription pill bottles, including Vicodin and diazepam, a.k.a. Valium.

A former Breitbart reporter, Lee Stranahan, who followed the “Dangerous Faggot” tour closely, tells me he’s concerned. “I’m praying for Milo,” he says. “A lot of people are worried about him.”


Back at the Meme Mansion, Milo is discussing plans for his September appearance during “Free Speech Week” at U.C. Berkeley, where he is scheduled to speak alongside other polarizing figures on the right, including Stephen Bannon and Ann Coulter, another friend of Milo’s. (As of posting, neither have confirmed their attendance, and one of Milo’s close associates, Lucian Wintrich, has announced that the whole week has been canceled, although Milo tells me otherwise.)

Among the twentysomethings he surrounds himself with, there’s a fear that “Free Speech Week” could turn into another Charlottesville. Milo, like Johnny Rotten floating down the River Thames, is banking on it, as if he takes perverse pleasure in knowing he can turn a college campus into a war zone. Sitting behind his desk, he strategizes ways to merchandise the chaos.

Hopefully, God smiles on us and Antifa comes out and fire-bombs the entire university.

“I believe the challenge for us is to create something so attention-grabbing that it produces another U.C. Berkeley and I can sell another 100,000 copies of the book,” he tells Macris, half-jokingly, referencing the turmoil that erupted when he was invited, and then disinvited, to speak on the campus in February. “Hopefully, God smiles on us and Antifa comes out and fire-bombs the entire university.”

He then moves on to prepare for a Skype interview with right-wing YouTuber Rusty Humphries. He’s wearing a buttoned-up, Republican caricature outfit, which is just British enough to project an aura of class superiority. “No matter how aloof or snooty you are, you simply can’t beat this accent,” he says, dressed in a Savile Row-tailored suit he cautions me “costs more than your education.” After the interview, Milo takes me through the footage as if he’s giving me a lecture on the Kennedy-Nixon debates from 1960. “You see that?” he says. “What conservative looks like that? Tell me? None. My body language is a master class.”

Across his desk, sweating away behind a rack of camera equipment, is his tireless cameraman, Matt Perdie. Perdie, who’s almost never referred to by his first name, is wearing a “Defund Berkeley” T-shirt he earned while accompanying Milo during last year’s “Dangerous Faggot” tour. At each stop, Antifa protesters attempted to bully Perdie, who’s either fearless or completely batshit. “Police! He assaulted me!” he’d yell in his nasal voice, doing what he’s been hired to do: risk his life for Milo. Many of his boys would.

In the driveway there’s a brand new black Corvette Milo purchased for Hayden, a mostly apolitical shitposter who’s seems to be all id. He separates his time between walking Milo’s dog, playing Xbox, and helping coordinate Milo’s outfits. One night, the Colorado transplant with a wavy mane that covers most of his face tells me he hates living in Miami because nobody “fucking speaks English.” Hayden seems nothing less than bored by politics, as though his allegiance to Milo is based solely on the lifestyle perks, like starting shit on the internet and racing his Corvette. He echoes South Park creator Matt Stone, proclaiming: “I hate conservatives, but I really fucking hate liberals.”

Milo’s most ideologically un-woke employee is Mike Ma, also in his early twenties, who’s MILO Inc.’s blond creative director who designed the company’s German Gothic logo, as well as the cover art for Dangerous. At a glance, Mike comes off like a 1980s teen movie bully on downers. Milo says he “plucked him from obscurity.” “You have a very highly developed natural aura of disgust any time you talk about anything that isn’t AK 47’s,” Milo tells Mike, who’s also a kind of pseudo-men’s rights activist who’s attempting to remove any traces of estrogen from his body with a strictly anti-soy diet. “It makes you a woman” he tells me, wearing his signature blue collared shirt and khaki pants. “It kills your testosterone. It kills your libido.”

Mike’s sadistic sense of humor has him taking the lead on writing jokes about the trans military ban, which he’s been researching by watching gender reassignment surgery videos on 4Chan.

“A funnier joke would be about transgender suicide rates,” says Milo.

“Tranny Pearl Harbor?” says Mike, who sounds off a few more ideas.

Milo cuts him off: “OK, this is at a six and I need it at a nine.”

“You sound like a disappointed father,” says Mike, who’s seems vaguely amused with the exchange.

Milo then turns to me, whispering below his breath so that only I can hear him. “I sometimes feel like a brothel madame or drag mom running a frat house.” But if there’s one thing Milo craves more than anything else, it’s to be loved by his boys, because for him, they represent the nation he’s building, which will be divided between the people who think he’s funny and those who think he’s psychopath.

He looks up at both Mike and now Hayden, who’s standing there half-asleep, in basketball shorts and a My Chemical Romance hoodie. “Why don’t you do something like, ‘War, terror and bloodshed are disgusting, but you know what’s even more disgusting? Cutting off your penis and inverting it.” They all laugh, including Mike.

In many ways, Mike’s the target demographic of MILO Inc., the shameless right-wing male who lurks The_Donald subreddit, who sees Milo as his way of scoring “hot skinny blonde Republican bitches,” the mini-Tomi Lahrens at campuses like Southern Methodist University that breed future White House interns.

It’s not just nationalistic frat boys or trolls who might opt into MILO Inc. Milo acts as a release valve, or conduit for raw expression for anyone who’s ever been publicly shamed on the internet for their “white privilege,” or had their use of pronouns policed on Twitter. For them, his fans, Milo expresses what they cannot: Cheeky cruelty, with a paternal wink.

By the end of the evening, Milo breaks the news to Macris: The “tranny” skit simply isn’t on-brand enough for Milo, who’s no longer willing to gamble with his product.


There was a time when Milo didn’t give a shit about the fragility of his brand, or what anyone else thought, for that matter.

“He was very fasch-y when I met him,” says Richard Spencer, the well-groomed poster boy of American white nationalism, who discovered Milo in early 2016 while reading Breitbart’s “An Establishment Conservative’s Guide To The Alt-Right.” Penned by Milo and Allum Bokhari, the guide provided a didactic breakdown of the philosophy of the growing radical right-wing movement.

“I never had an opportunity to have an intellectual discussion with him about what he was doing. He was always moving around. He was always in performance mode,” Spencer tells me. He quickly figured out that Milo was what many now believe him to be: an ideological shapeshifter who takes on new forms when it benefits him.

Milo’s persuasively acerbic rhetoric, rallying conservatives around his fuck-all approach to defending his race and gender, has nonetheless found a fanbase among the white nationalist movement, which, of all the things he’s done, will go down as the most genuinely dangerous. In his guide to the alt-right with Allum Bokhari, he says: “The alt-right believe that some degree of separation between peoples is necessary for a culture to be preserved.”

Right-wing journalist and former Breitbart editor-at-large Ben Shapiro has openly criticized Yiannopoulos for popularizing the alt-right. “He was very instrumental in mainstreaming in the alt-right and treating the alt-right like an intellectual movement that should be respected and given its fair hearing,” he says. “This was his shtick—to pander to the alt-right.”

But just as Milo claimed during the aftermath of his comments about sex with minors that he had always condemned child abuse, he has repeatedly dodged his affiliation with the alt-right and white nationalists, claiming he spent part of his “Dangerous Faggot” campus speak tour denouncing racism.

“Where is the evidence I pandered to racists?” Milo asks me. “I don’t care about [racists]. There’s like, 3,000 of them anyhow.”

Yet Milo can’t argue with the fact that he has repeatedly stoked the flames of white male outrage, reaching its apex with a particularly troll-y campaign called “The Privilege Grant,” a scholarship fund he launched in January of 2016, strictly for white males.

“It started off as a joke, to bait social justice warriors and wind up liberals,” he tells me. “Then I found the data showed that white working class boys were some of the most educationally underprivileged group in society and some of the most underserved by scholarships. So it seemed to achieve two objectives at once: Once to attract the fury of the progressive left and help a few kids who needed it.”

I push back: Can he truly not see how this made him a symbol of white nationalism?

“No, I don’t. How could it? At the same time I was giving speeches about the perils of white pride [on the “Dangerous Faggot” tour] and how to destroy the alt-right.”

The Privilege Grant Foundation raised between $100,000 to $250,000 in the first few months, which was set to be “awarded in early Summer 2016 to be available for Fall 2016 enrollment” to 50 white, male and economically disenfranchised students. But Milo, a British national, had never dealt with the IRS before, and his inability to secure tax exempt status resulted in the funds never getting to the students, as deadlines were missed, and the Privilege Grant fell into limbo.

Reports began to emerge that Milo was depositing the donations into a PLC using bank transfers from applicants, which was potentially unethical and illegal. “Anything that could be disputed and refunded, like PayPal, was avoided,” says Margaret MacLennan, a right-wing social media personality who says she was director of the fund.

“Look, there’s a legal entity. A legal nonprofit. A staff,” Milo says. “We’ve already awarded the pilot program grants. Those people will have the money directly deposited into their student accounts at their chosen Universities when they matriculate.”

(As we researched this piece, playboy has retrieved a letter of exemption stating that the not-for-profit’s application for 501©(3) status, which was refiled in May, has been approved by the Department of the Treasury.)


It’s July 27, and Dangerous has been on the best-seller’s list for weeks. It’s losing momentum, however, behind an onslaught of negative press accusing MILO Inc. of exaggerating sales figures. MILO Inc. initially claimed it sold 100,000 books in the first week. In reality, they had shipped that number to bookstores, retailers and wholesalers. Based solely on Nielsen BookScan numbers, the industry standard, which doesn’t account for factors such as wholesale shipments, the number was a miscalculation.

“We should be number one,” he tells Macris by phone. “They only do this to Conservatives. They are trying to fuck us. We now have have to decide whether we go to war with them.”

The pair then discuss an earlier Facebook trolling campaign, organized by MILO Inc. employees, in which fans urged Barnes and Noble stores to stock the book. At the end of July, the bookseller, which initially only carried the book online, decided to stock its shelves with copies of Dangerous, which Milo likens to the retailer dodging a bullet, “or rather, a MOAB.” The victory only reinforces Milo’s belief that the New York Times best-seller’s list suppresses sales numbers of books by conservative authors.

When I ask Milo if he’s going to troll the Times best-seller’s list, or sic his followers on them, he responds like a much more seasoned politician, who’s back on the campaign trail. “No, that’s Milo of 18 months ago.”

Still, there are more battles on the horizon. Milo has been exchanging fire with the D.C. metro authorities, who pulled posters advertising his book because they claimed it violated their terms. “My face in now literally a hate crime,” he says. There is some bitter irony in the fact that his case in D.C. has been taken up by the ACLU, which is also representing PETA and an abortion clinic in the same First Amendment suit.

Not that that would in any way inhibit his ongoing crusade to offend and intimidate the left into giving up its corner on cool, which is the foundation of his fledgeling empire. One can only assume there will be collateral damage—careers destroyed, self-harm, financial ruin. But that loose-cannon persona has also been his most attractive quality for his fans. For Bannon—with whom he’s allegedly in discussions to get his old column back—he’s a disruption tool, the “gay hooker” who can shake things up.

The whole thing may be nothing less than a gamble for MILO Inc. investors, as anyone willing to vet Milo will soon realize his motivations are solipsistic, a vainglorious pursuit of becoming the most famous conservative spoofer of his generation, as he seeks respect outside of the ghettos of right-wing media by waging war, rather than diplomacy—which is Trumpian, to be sure.

“I want to bring people together, through laughter and war,” he tells me, the contradiction outrageous. “I’m really a pleaser, you see. All I ever wanted to do was make people smile.”