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Milo Yiannopoulos Is the Pretty, Monstrous Face of the Alt-Right

A new force in electoral politics.

By Joel Stein
September 15, 2016
Photographer: Guy Martin for Bloomberg Businessweek  

At 4 p.m., Milo Yiannopoulos puts on a pair of glasses for the first time today. He examines himself in a mirror to see if he wants to add a gray suit to his purchases, which will push his bill to almost $12,000 at Savile Row’s Gieves & Hawkes. He’s buying clothes for his next round of college speeches in, as his bus announces in huge letters next to five giant photos of him, the Dangerous Faggot Tour. It resumed at Texas Tech University on Sept. 12 and is scheduled to hit campuses including Columbia, Dartmouth, the University of Alabama, and the University of California at Berkeley before concluding at UCLA in February. “I have ridiculously bad eyesight, but I have learned to live with an impressionistic view. Life is a Monet painting,” he says, taking off his glasses. “I wander around enjoying myopia.”

Yiannopoulos is the 31-year-old British tech editor and star writer for Breitbart News, where he’s the loudest defender of the new, Trump-led ultraconservatism, standing athwart history, shouting to stop immigrants, feminists, political correctness, and any non-Western culture. Yiannopoulos gained his initial fame as the general in a massive troll war over misogyny in the video game world, known as Gamergate. He was permanently banned from Twitter in July after the social media company said his almost 350,000 followers were responsible for harassing Ghostbusters star Leslie Jones. He still has nearly 275,000 subscribers to his YouTube speeches, and CNBC and Fox turn to him as the most notorious spokesman for the alt-right, the U.S. version of Europe’s far right (led at various times by England’s Nigel Farage, France’s Marine Le Pen, Austria’s Jorg Haider, the Netherlands’ Geert Wilders, and Germany’s Frauke Petry). Their followers’ politics are almost exactly the same: They’re angry about globalization—culturally even more than economically. They’re angry about political correctness guilting them about insensitivity to women, minorities, gays, transgender people, the disabled, the sick—the everyone-but-them. They’re angry about feminism. They don’t like immigrants. They don’t like military intervention. They aren’t into free trade. They don’t like international groups such as the European Union, United Nations, or NATO—even the International Olympic Committee. They admire the bravado of authoritarians, especially Vladimir Putin. Some are white supremacists. Most enjoy a good conspiracy theory.

Featured in Bloomberg Businessweek, Sept. 19-25, 2016. Subscribe now.
Photographer: William Mebane for Bloomberg Businessweek

But members of the alt-right, unlike their old, frustrated European counterparts, are less focused on policy than on performance. Their MO usually involves pissing people off with hypermasculine taunts. They call establishment and even Tea Party Republicans “cuckservatives”—because they are cuckolded by the Left. They do most of their acting out online, often by organizing on 4chan or Reddit and then trolling targets on Twitter. The alt-right is a new enough phenomenon that in August, Republican House Speaker Paul Ryan—running against an alt-right candidate in a primary—mistakenly called it “alt-conservatism” on a radio show. “It’s a nasty, virulent strain of something,” he said. “I don’t even know what it is, other than that it isn’t us. It isn’t what we believe in.”

As Donald J. Trump has become the candidate of the alt-right, Breitbart News has become the movement’s voice. The two merged semiofficially in August, when Breitbart’s chief executive officer, Steve Bannon, quit his job to run Trump’s campaign. And Yiannopoulos, whose byline on the site is simply “Milo,” is Breitbart’s most radioactive star.

“Milo is the person who propelled the alt-right movement into the mainstream,” says Heidi Beirich, who directs the Intelligence Project at the Southern Poverty Law Center, which tracks hate groups and describes the term “alt-right” as “a conscious rebranding by white nationalists that doesn’t automatically repel the mainstream.” Beirich says she’s not even sure if Yiannopoulos believes in the alt-right’s tenets or just found a juvenile way to mix internet culture and extreme ideology to get attention. “It’s like he’s joking: ‘Ha ha, let me popularize the worst ideas that ever existed,’ ” she says. “That’s new, and that’s scary.”

“I don’t let feelings control my life. I’m more disciplined than other people”

Despite being the alt-right’s mouthpiece, Yiannopoulos won’t say for certain if he’s one of them. Earlier that day, lounging on a couch in the living room of his apartment, located in a huge residential complex a good 45 minutes from Central London, he replaces Wagner with Chopin so he can talk more easily. He turns to Allum Bokhari, a 25-year-old half-Pakistani Oxford graduate, who used to work for a Liberal Democratic member of Parliament and now writes for Yiannopoulos at Breitbart, and asks, “Am I a member of the alt-right?”

“No,” says Bokhari, who wears a white dress shirt, gray blazer, and gray trousers to work at a desk next to a garment rack in Yiannopoulos’s living room. “Because they wouldn’t have you. You like Israel a lot more. Some on the alt-right would describe you as a degenerate.”

Yiannopoulos, wearing a pearl bracelet, a huge diamond in his ear, and a necklace with a gold dog tag, nods in agreement. His nods shake his blond extensions. He likes to brag that he’s a bottom for tall black men and that he used to hold a paint sample called Pharoahs Gold 5 to men at clubs to see if they were dark enough to have sex with. He wants to self-publish a Kindle e-book so he can go on television shows with the chyron “Author of Satisfying the Black Man Sexually,” though he’d need to alter the title slightly, because the book Satisfying the Black Man Sexually is already on his shelf. “That’s why I don’t like Planned Parenthood. They kill all those black babies. In 20 years, they could be my harem,” he says. He sees no room for white gay men in liberal parties anymore, because all white men, he says, are treated as enemies of multiculturalism. Plus, he says, being a gay Republican reinstates the illicitness that homosexuality has lost.

During the Republican National Convention, Yiannopoulos hosted a party in Cleveland called Gays for Trump. He walked up to a podium backed by photos of skinny, shirtless young men wearing Make America Great Again hats, then removed a bulletproof vest to reveal a tank top with a rainbow fist holding a gun and the words “We shoot back.” His Cleveland speech was attended by Daryush “Roosh” Valizadeh, whom the liberal website the Daily Dot called “the web’s most infamous misogynist,” and Richard Spencer, a smartly dressed, University of Virginia-educated white supremacist who came up with the term “alt-right” in 2008. Yiannopoulos says white supremacists make up a tiny fraction of the alt-right, and he doesn’t approve of them, though he’s not going to kick Spencer out of his events. “I don’t see it as a bad thing that I surround myself with edgy people,” he says. “Because they’re interesting. I’m not going to not hang out with someone because the New York Times calls him racist.”

Photographer: Guy Martin for Bloomberg Businessweek

Yiannopoulos’s favorite political tactic is trolling. In the alt-right worldview, nice, normal white dudes are told they’re racist and sexist by “social justice warriors.” In retaliation, they’ve adopted a strategy Yiannopoulos calls “double down, don’t back down.” He explains: “If someone calls you an anti-Semite, you go to their page and put up swastikas.” Then those he’s offended, he says, use this prank as false proof of the original accusation of anti-Semitism to gain power through sympathy. Yiannopoulos’s mob of trolls then mock them for taking the prank seriously and whining. Nobody’s actions can be taken at face value. “Everybody is trolling everybody, and nobody knows who is winning,” he says. And at least his side is enjoying it.

“We live in a post-fact era. It’s wonderful,” he says, pointing to various web pages on his giant computer screen that show photos of, supposedly, Bill Clinton’s grown black son. “The Washington Post gives a truth check, and no one cares. Now you have to use the truth and other strategies. You have to be persuasive. Dumpy lesbian feminists and shrieking harpies in the Black Lives Matter movement are not persuasive,” he says, digging into the egg, turkey, and avocado scramble prepared by his full-time trainer.

In this Kafkaesque troll war for America’s soul, Yiannopoulos believes that all offense is performed rather than truly felt. “I have never been offended. I don’t know what it means. It’s not that I disagree with it. I don’t understand it. I’ve never had that feeling,” he says. “I don’t let feelings control my life. I’m more disciplined than other people. I have a dark, ADD, Asp-y [Asperger’s syndrome] brain. I’m totally autistic or sociopathic. I guess I’m both.”

Although he works for a news network, Yiannopoulos considers himself to be a pop star. “Milo is much closer to Jon Stewart,” says Alexander Marlow, the 30-year-old editor-in-chief of Breitbart. “He uses entertainment to put out the news. Only he’s much more fabulous and better-looking.”

There are almost as many articles about him on Breitbart as by him. Some end with a list of all the clothing items he’s wearing and their prices, like in a fashion spread. Yiannopoulos says he has endorsement deals with some designers, though he claims they don’t want to be named for fear of social justice warrioring. The rider in the contract for his college tour demands defuzzed peaches and dethorned roses. He’s shooting an alt-right rap video in Los Angeles, where he says he’s about to close on a $3 million house in the Brentwood section, which he hopes to pay for partly with proceeds from a book he’s finishing called The Dangerous Faggot Manifesto.

For his shopping trip to Gieves & Hawkes, Yiannopoulos calls for an Uber. The driver is a man, possibly because Uber’s algorithm has learned that Yiannopoulos rejects female drivers. Women, he says, have been scientifically proven to be worse at spatial relations, as have Asians. “It’s the only thing Saudi Arabia gets right,” he says about the country’s ban on female drivers. “Behind every racist joke is a scientific fact.”

He says he disapproves of all Muslims—except his boyfriend of 10 years. But it’s feminists who rile him most. During Gamergate, he targeted game developer Brianna Wu. Her address was posted on Reddit, and she received so many rape and death threats that she moved out of her home for a while and hired a bodyguard. “When you’ve faced difficulties in your life—growing up gay, being a minority, suffering from physical illness—you have two paths in front of you,” Wu says about Yiannopoulos. “Some people develop a fierce sense of empathy. The other side that’s available is to become something very dark. You can look at some of his poetry, when he was an adolescent, and it’s very clear he was hurting. He’s channeled that pain into hurting a lot of people and justifying it.”

But Yiannopoulos says he’s a crusader in a righteous cause, opposing the cultural tyranny of the Left. In addition to policing video games, comic books, sci-fi movies, and college campuses, Yiannopoulos feels the Left is also winning the fight to define what’s funny, citing Chris Rock’s and Jerry Seinfeld’s complaints that comedians can no longer push boundaries when performing on campuses. “The only ones succeeding in comedy are the ones playing victim, the wretchedly unfunny Amy Schumers,” he says. “She explicitly sends the message that they should behave like a man—burp and fart and shit and have lots of sex. And these women are going to wind up lonely. If you give a shit about impressionable young women, you have to hate Amy Schumer.”

Although he gets compared to Ann Coulter and called the face of a political movement, Yiannopoulos says what he really cares about is pop culture and free speech. “I don’t care about politics,” he says. “I only talk about politics because of Trump.”

“I think my legacy might be longer than Trump’s. I’m attacking the disease, not the symptoms. Also, he doesn’t read. But I still love him. And he’s still my daddy. Nobody’s perfect”

Breitbart, he argues, normalized the combative, audacious attitude the Republican nominee has used. “Trump capitalized on what we had been charting. He couldn’t have done it without us,” says Yiannopoulos, who’s the honorary moderator for Reddit’s biggest Trump community, which has more than 200,000 subscribers. “Mr. Trump may have already won the only war we care about. Fewer and fewer people are going to be fired for having these opinions.”

“I think my legacy might be longer than Trump’s,” he says. “I’m attacking the disease, not the symptoms. Also, he doesn’t read. But I still love him. And he’s still my daddy. Nobody’s perfect.”

Yiannopoulos is a reader of both German philosophy and treatises on sexuality based on racial stereotypes, though he wasn’t a great student. He grew up in a small town near Kent, England, and dropped out of the University of Manchester and then Cambridge. A practicing Catholic (though he likes to mention that his maternal grandmother was Jewish when he’s accused of anti-Semitism), he wrote for England’s the Catholic Herald and was later fired as a tech writer for the Daily Telegraph. He started a tech news site called the Kernel, which ran up a large debt and feuded with the writers to whom much of the debt was owed; it was eventually sold to the Daily Dot in 2014.

Once he was hired on the recommendation of a friend at Breitbart about two years ago, Yiannopoulos flourished. Ben Shapiro, the site’s previous star writer, quit when Breitbart went from far-right to alt-right, with Yiannopoulos gleefully leading the pro-Trump rhetoric. “He likes to say this is all ironic mischievous trolling,” Shapiro says. “If I can’t tell the difference between your ironic tweet and David Duke’s, that’s your fault. He’s not making fun of racism. It’s clown nose on, clown nose off. It’s basic teenage bullshit by someone who is immature.” Shapiro says he doesn’t even look at Breitbart anymore. “I don’t have to watch Psycho every couple of days to realize Anthony Perkins is a bad person.”

Photographer: Guy Martin for Bloomberg Businessweek

While Shapiro’s usual far-right speeches often cause protests on campuses, Yiannopoulos puts on a whole show to provoke students. He says his tour will cost $1 million, only some of which is going to his wardrobe. While on the road, he’s giving a women-in-tech talk at Stanford about female biological inferiority in science. He’s going to Yale shortly before Halloween, where, dressed in traditional Native American garb, he’ll address last year’s campus protests about mocking other cultures via culturally insensitive costumes. “I’m a perpetual 14-year-old,” he says. “Maybe not 14. I’m 7. It’s my USP [unique selling point].”

After the suit buying, Yiannopoulos heads to Claridge’s, where his grandmother took him every fortnight for high tea. He lived with her as a teen and says her death two years ago was the only bad thing that’s ever happened to him.

Yiannopoulos may well be in post-fact mode when talking about his family and his finances. Ordering a Cobb salad and green tea, Yiannopoulos says that before he was born his father told his mother he wanted a divorce, but his mom told him she was pregnant. His parents stayed together for six more years and then split. Yiannopoulos respects his father greatly and lived with him for a little while in Kent, where they had a live-in housekeeper and cook. But he hasn’t seen his father in years, never having visited him and his Jamaican wife in St. Ives in southwest England. “I’ve never thought about it!” Yiannopoulos says, snapping his fingers after mentioning his dad’s black wife. “That’s where I get my coal burning from.”

“My dad is terrifying. He’s like Tony Soprano but Greek. He does unspeakable things during the day and comes home and listens to Wagner and drinks fine wine,” he says, laughing. “I would think, If my dad is just a doorman, why do we have such a nice house? Then I saw it on The Sopranos.” He won’t elaborate. Yiannopoulos missed his annual phone call with his father last Christmas, when his dad called his assistant instead of him.

Yiannopoulos almost never talks to his mom either. She married a guy who, he says, was tough on him as a kid. “My instinct was, ‘I’m going to get you back.’ ” He says he did, 10 years ago, in a way that’s not legal, and his mom’s husband has been nice to him since. “I have never lost a battle, because I have nothing to lose,” he says. “You don’t fight a pig, because you both get dirty. I like the muck. Nothing is too low-rent or dirty enough for me.”

Waiting for his salad, Yiannopoulos sips his green tea and checks his texts. “Oh, no!” he yells. “Leslie Jones nude photos! No one wants to see that.” The female-led, feminist-tinged remake of Ghostbusters, in which Jones co-starred, was an affront to the alt-right, and Yiannopoulos wrote about his hatred of the film, calling Jones a “black dude.” Jones was harassed on Twitter so badly that the social network banned Yiannopoulos, who went under the name @Nero—his favorite leader—accusing him of marshaling some of his 338,000 followers to abuse her. Now someone has hacked her phone and put up her photos and home address on her own website. “This is the worst thing ever. Now she’s going to get all this victim status. This is what feminists do,” he says. “She’s a public figure. We have no privacy. Get over it.” Still, Yiannopoulos would rather the name of his boyfriend and the location of his apartment weren’t exposed. He’s received a syringe in the mail, and outside his building someone dropped a dead mouse with a razor blade inside. He says this was difficult for him. But only because he had to give his housekeeper, who opens his mail, a raise.

It’s unclear to Yiannopoulos the next morning how many people are in his apartment, even though his place isn’t very large. There’s a friend’s niece, who’s staying a while. His trainer is definitely here, nursing the first half of a huge tiger tattoo he got on his forearm the previous day. Bokhari is back, dutifully typing Breitbart articles in the living room next to co-worker Charlie Nash, an 18-year-old libertarian wearing a black denim jacket with a Clockwork Orange pin, whom Yiannopoulos hired after Nash interviewed him for his own website. “I haven’t been alone in a room for four years. Not for more than an hour,” Yiannopoulos says.

Photographer: Guy Martin for Bloomberg Businessweek

He inputs all of his friends into a spreadsheet, with columns for attractiveness, intelligence, income, and politics (listed either “pass” or “fail”). One column lists whether he should hold, long, or short them, like stocks. Many of the people he surrounds himself with are paid staff. All, besides a female publicist and a gay assistant in New York, are straight men. “I don’t generally employ gays. I don’t trust them. They don’t show up on time. They don’t do the work. They get all queeny with drama,” he says. “I like straight white men. They do the work. I like black guys for my love life, straight white males as employees, and girls as drinking buddies.” He doesn’t drink anymore.

Although some of his staff are paid by Breitbart, Yiannopoulos says he’s got almost 30 people on his payroll at a total cost of about $1 million a year, not including his salary. “My salary is really big, too,” he says. Some of this is paid for by donations from conservatives. Some comes from family money. Yiannopoulos says he and a business partner bought several apartments in his huge complex years ago when it was first built, slowly selling them off for a profit. He says he also hangs around a lot of rich people, some of whom were his sugar daddies. Last time he was in Los Angeles, he says, a white man at the Sunset Tower bar hit on him and gave him $10,000 after having sex with him twice and another $10,000 the following night.

Tonight, Hillary Clinton is in Reno, Nev., delivering a speech on the alt-right. Yiannopoulos loads it up on YouTube, where the alt-right has taken over the comments section, a furious scroll of swastikas, “nigger”s, and “build the wall”s. The speech has been postponed by three hours, and Yiannopoulos is convinced it’s because Clinton is gravely ill. “Is that a catheter in her shirt?” he says as soon as she enters the frame. “Listen to her voice! She’s sick!” he yells about her hoarseness.

Halfway through her speech about the conspiracy-pandering and racism of Trump and the alt-right, Clinton reads four Breitbart headlines. Two of them are from Yiannopoulos articles.

“Birth Control Makes Women Unattractive and Crazy”

“Would You Rather Your Child Had Feminism or Cancer?”

He stands up, claps, and spins around. Yiannopoulos has hit the troll jackpot: He wrote outrageous headlines trying to provoke liberals, and the world’s top liberal read them with head-shaking seriousness, falling for the prank. He directs Bokhari, sitting 5 feet away, to quickly write an article for Breitbart about this. They give it the headline “Milo to Hillary: You Did This.” As crazy as that sounds, once you understand troll logic, it’s pretty much true.

Updates to clarify that Jorg Haider, who died in 2008, is not currently a leader of Europe’s far right.