Backed by a $12 million investment from a Clinton-hating billionaire, the alt-ight’s fallen boy toy is planning a massive comeback. Cue the Jihadi strippers and angry Jewish dwarves.
Illustration by Edel Rodriguez
Milo Yiannopoulos—the queeniest pundit ever to be embraced by conservatives—is having a book party. The incendiary right-winger, overt about his love of white pearls and black men, is celebrating the June publication of Dangerous, a slim, self-published volume of attacks on progressives, feminists, Black Lives Matter activists, and Twitter that jumped straight to number one as soon as preorders opened on Amazon. It’s the same book that was canceled by Simon & Schuster after Yiannopoulos seemed to advocate sex between boys and adult men in a long-forgotten interview.
The event is being held in (certainly not on) the DL, a three-story club on the Lower East Side of Manhattan that’s described in Yelp as “sexy” and “sultry,” but whose packed, humid confines, ringed with red-and-green lamps, evokes a Christmas Day in Hell. Unlike the typical Manhattan publishing party, the concerns extend way beyond the wine running out too early. This being a Milo Yiannopoulos book party, 13 uniformed police officers are stationed outside. This being a Milo Yiannopoulos book party, a woman dressed as Hillary Clinton in an orange prison jumpsuit sits in a dunk tank. This being a Milo Yiannopoulos book party, there is a group of dwarves wearing yarmulkes, hired to mock a short, Jewish journalist and Milo antagonist, all wearing “Ben Shapiro” name tags and bibs that say, “It’s my bris and I’ll cry if I want to.”
The party is the embodiment of Milo’s essence: as if Richard Spencer, Joan Collins, and Don Rickles were thrown together in a blender.
Among Milo’s special guests are champagne-sipping Pharma Bro Martin Shkreli, who has been called “the most hated man in America” for raising the price of an AIDS drug 5,000 percent and is a month away from being convicted of securities fraud. At one point in the evening, strippers emerge from floor-length burqas to pummel Yiannopoulos with a dildo, a meat cleaver, and a baseball bat.
It would be penance if he were penitent. “Simon & Schuster shareholders are going to be very sorry,” he tells Page Six against a wall of TV screens flashing unkind quotes about him by various pundits. “I picked myself up and got back to work. I discovered that people were very understanding. It’s something that I like about America: people are understanding and forgiving. If they get the sense that you’re aware that you fucked up and are sorry, they’re very willing to forgive.” He adds, “If you come for me, you better leave me in a coffin.”
The next morning, nursing whatever marks are left on his body by the dildo attack, Yiannopoulos files a $10 million lawsuit against Simon & Schuster, citing damage to his professional future. It is only the beginning of his revenge on the world, which, he claims, will be fueled by a new multimillion-dollar war chest.
Amid the cacophony of messages at the Dangerous party, one was paramount: the troll was peeking out from under the bridge. He had been exiled from impolite society since February, and that was enough.
For the record: on a video podcast, he said that sex between men and 13-year-old boys was acceptable if the boy was sexually mature. He also thanked a priest for teaching him how to give good head as a child. “We get hung up on this child abuse stuff,” he said in the video. “This is one of the reasons why I hate the left, the one-size-fits-all policing of culture, this arbitrary and oppressive idea of consent.”
Cue trap door.
If anyone could ride pedophilia to professional triumph, it would be Yiannopoulos, who has long displayed a Judy Garland-esque ability to wring success out of the sad and unspoken. For our purposes, Milo’s bilious bildungsroman begins in 2015, when the college dropout and Guardian technology journalist relocated from the U.K. to serve as tech editor at the right-wing website Breitbart, an early architect of the so-called “alt-right” that was financed by billionaire Robert Mercer. Led by Steve Bannon, who would later become a top White House advisor, Breitbart helped propel Donald Trump to power. Milo immediately made his mark covering “Gamergate,” a sexual-harassment scandal in the videogame industry that lent itself to macho priggishness, which he happily provided. Future Trump supporters lapped it up.
Yiannopoulos himself was an early Trump supporter, referring to the candidate as “Daddy.” He started a grant program for heterosexual white men. He opined that being gay was “aberrant,” and that gay men should “get back in the closet.” He traveled the lecture circuit, or tried to; one speaking engagement at the University of California-Berkeley was canceled amid violent protests, which delighted him. He was banned from Twitter in July 2016 for racially slurring SNL cast member Leslie Jones.
Then, Valhalla: he was scheduled to be the keynote speaker at CPAC 2017, the annual conservative Lollapalooza, appearing alongside Mike Pence, Steve Bannon, and Ted Cruz. It was a remarkable achievement for a 32-year-old Brit who had been writing about video games three years earlier. CPAC was to be Milo’s crowning moment.
But 24 hours before the convention was to start, Milo’s carefully crafted world came tumbling down. Pedophilia turned out to be a step too far even for his politically incorrect supporters. Yiannopoulos later insisted that his comments on priests and boys had been misconstrued. But the tape of the conversation spoke for itself. In short order, he was disinvited from CPAC, resigned from Breitbart in disgrace, and lost both his book deal and his $255,000 advance from Simon & Schuster. While those blows might have chastened meeker souls, Yiannopoulos was unbowed. He went underground, or as close to underground as possible for him.
Today he contends that, with the exception of the canceled book deal (“the only thing that really caused me damage”), the scandal actually helped him by dramatically raising his profile. At Breitbart, he says, “the Milo problem” really boiled down to the fact that the Texas-based publication “wasn’t set up to incubate media stars.”
Appropriately, he has created a movie-star life for himself, with cars and drivers, thrones (on which he was carried into a speaking engagement at the University of California-Santa Barbara in 2016), and a personal trainer who travels with him around the country.
Now he wants to spread his stardust far and wide. He has decided to establish his own factory of conservative media stars, with himself, of course, at the top. It’s named—what else?—Milo.Inc. The business model assumes that Milo is so beloved, and his worldview so necessary, that the public wants to see him cloned into other bodies, on multiple platforms, in person, and across the country, forever and always.
When we first contacted Milo for this story, he expressed his resistance to cooperating with a “gay rag.” But when he finally agrees to an interview, he’s articulate, combative, and confident, as usual. “I’m going to invent the whole industry,” he says of his plans for Milo.Inc. “I’m going to own all the stars and I’m going to develop all their careers. I’m going to own the network that they’re all on. I’m going to not just have, like, the three- or four-million audience that Bill Maher has; I’m going to have a 40-, 50-million audience, because half this country isn’t being served by the entertainment industry at all.”
He wants to do what Glenn Beck tried to do with The Blaze—but not really, because Glenn Beck is “a fucking mental case who failed spectacularly because he has no sense of humor and no idea of what makes a good entertainment star.”
And, he claims, he has a bulging purse to realize his vision: $12 million in seed money.
And, he claims, he has a bulging purse to realize his vision: $12 million in seed money, although that can’t be confirmed. In July this year, BuzzFeed reported that leaked documents show Milo has been financially supported, since his Breibart departure, by Robert Mercer, a hedge-fund billionaire/conspiracy theorist who is often described as “reclusive” and “eccentric.”
Mercer, who almost never gives interviews, entered politics wallet-first around 2010, driven by a blinding hatred for Bill and Hillary Clinton—specifically, he was convinced that they were murderers. During the 2016 election, with the help of Kellyanne Conway, he founded a Super PAC designed to get Ted Cruz elected. When Cruz cratered during the primaries, Mercer threw his support to Trump instead.
Today, with Trump installed in the White House and Breitbart providing a smashing return on his investment, Mercer has turned to Yiannopoulos to further expand his media portfolio.
The April 2017 debut of Milo.Inc was accompanied by a frothy press release announcing that the organization’s guiding principle would be “making the lives of journalists, professors, politicians, feminists, Black Lives Matter activists, and other professional victims a living hell.”
Milo has clear ideas of what he does and does not want. He wants more followers, more fame, more speechifying, more gratuitous jibes at the folks he loathes most. He wants his own TV show. He wants more-more-more ratings and attention, all of which can be monetized. He also wants to amass a stable of his own authors, as long as they, like him, have a large “portable audience.”
Even before Charlottesville, Milo seemed to be inching away from some of his alt-right cronies. He says he doesn’t want anything to do with white ethno-state enthusiast Richard Spencer, whose lexicon is peppered with the language of the Third Reich. But Milo seemed perfectly satisfied with Trump’s mealy-mouthed condemnation of Nazis, white supremacists, and “many others” after the violence in Charlottesville, and is dismissive of any suggestion that he himself played a role in allowing that ideology to fester. Nevertheless, the racist stench infusing the alt-right has prompted him and many of his closest followers to adopt the term the “new right” for their particular brand of politics.
It’s notable that his homosexuality, which would have been a career killer for an aspiring conservative powerhouse in an earlier time, is now almost a boon to his career. Conservatives aren’t exactly known for their young voices, much less one with an almost genetic ability to attract attention to the cause. They let him be; in return, he offers the party an injection of youth and glamor. Libertarians don’t care about his sexuality; it fits their hands-off ethos.
Yet there is significant risk he will poison the well. His polished nastiness often has spectacularly self-defeating consequences, like losing him his quarter-of-a-million-dollar book deal and his Twitter account. How willing will the Mercers be to back him if his impetuousness ends up damaging them and Milo.Inc.?
He says that he’d very much like to be allowed to return to the social-media platform, and even emailed Twitter CEO Jack Dorsey about it. He was told Dorsey wasn’t interested in a discussion.
For his part, Milo acknowledges that it will be difficult to become a media mogul without a working Twitter account. He says that he’d very much like to be allowed to return to the social-media platform, and even emailed Twitter CEO Jack Dorsey about it. He was told Dorsey wasn’t interested in a discussion.
Today, Milo works out of a Miami office building with a staff of roughly 30. He says his employees do everything from PR to tech support to sales and marketing—all the usual stuff that a staff of a small company would do. He’s in the United States as an immigrant on an O-1B visa, but remains a citizen of the U.K. He rents a couple of houses in Miami, and although he won’t talk about it, rumor holds that a boyfriend is close by.
The empire in his mind has three principal prongs: publishing, touring, and merchandise. The company’s publishing arm will target libertarian and conservative authors who can’t find a home with traditional outlets. Eventually, he’d like to open it up to less predictably conservative voices, such as dissident feminist authors. Take British author Laurie Penny, for instance, a controversial left-wing feminist who is a bit of a liberal Milo: she has come under fire for claiming that modern feminism is merely consumerism dressed up as female liberation. Milo detests her views, but her prose enchants him. “I think her feminism is poisonous and divisive and everything she says is garbage,” he says, “But I enjoy her company and her prose is beautiful and I’d quite like to publish her.”
This is emblematic of one of Milo’s main character traits: he tries to have many things both ways, which raises the question of how much of it he actually believes and what is performance. He is intensely decadent in that regard; he aligns himself with our racist president, yet he’s half-Jewish when it suits him. He openly dates people of color, yet talks explicitly about his fetish for black men in a borderline-racist way.
“I lift young black men out of poverty every day. Sure, the next morning my driver takes them right back there, but whatever,” he wrote on Facebook in January 2016. “Black men are notorious for lusting after a well-rounded Caucasian butt cheek. I speak from experience,” he said on Reddit in 2015. He rails against Muslims and immigrants, but is an immigrant himself. On Real Time with Bill Maher, he wore eyeliner and pearls while claiming that transgender people and gays have a “disorder” because they can’t procreate.
In this way, he is part of a perverse matched set with another right-wing blonde who has also been called a performance artist and likened to a drag queen: Ann Coulter. Most of what they say is less concerned with legitimate cultural critique than seeming as outrageous as possible. But with Trump in the White House, the unimaginably outrageous has become reality. Almost everyone else seems reasonable in comparison. In this environment, it’s questionable whether Milo’s brand of shock politics is a sustainable business plan; can he draw enough online traffic and sell enough books to scale a viable media company?
For now, Milo is focused on looking for YouTube stars who could “be the next Milo.” He laments that the field is pitifully thin. “You’ve got John Oliver, Jon Stewart, Bill Maher, all of these kind of hybrid entertainer/cultural commentators on the political left, all of whom are permitted to both tell jokes and break news and express political opinions,” he says. “There is absolutely nothing remotely similar on the right which is astonishing to me. So I’m going to invent it.” (Never mind that Fox News already tried, and failed, with The 1⁄2 Hour News Hour, a conservative version of The Daily Show that sank without a trace in 2007. The fact that much of the young audience he needs doesn’t find him funny might present another challenge.)
The other two Milo.Inc revenue streams are merchandise and touring. Milo claims that upward of 40 universities have agreed to host him starting in the fall. (The tours are not confirmed.) A one-week speaking rally is planned at UC-Berkeley, which has become ground zero for clashes between right and left. He hopes to bring the usual cast of right-wing pundits with him to those engagements—including Ann Coulter, David Horowitz, and “maybe a few liberals if I can convince them”—and sling merch, including tour T-shirts, fidget spinners, and apps. [After FourTwoNine went to press, word spread that Milo’s “Free Speech Week” in Berkeley was collapsing and likely to be cancelled.]
If Milo’s dreams all sound a bit like an opportunistic grab bag, that’s because they are. Positioning yourself as the media star of the future means covering all your bases. “I’m a free-speech warrior first, a conservative second,” Milo says. “I’m not interested in serving the far right. I’m not interested in serving lunatics. I’m interested in serving ordinary Americans who don’t see their own life-styles, opinions, and views reflected on television. And I’m going to start building shows and incubating stars for those people. I’m going to start creating formats for those people.”
High on his target list: the children of Gen Xers who are now becoming teens. “They hate feminism. They hate political correctness. They hate BuzzFeed,” he claims. “They really hate it. This is the market that I’m building a network for, and they fucking hate my entire generation.”