It seems the phenomenon of Milo Yiannopoulos – the brief, bright arc of his invention – is over. I do not want him to fall without being understood so I will tell you the strange tale of our encounters last year. Monsters should be understood, and pitied, for our own sakes.
It is midsummer and he is staying at the W Hotel on Times Square, close to where a $35,000 billboard of his face will soon appear to publicise his book Dangerous. Milo’s real face can, therefore, check on his paper face simply by looking up at the sky. The W is a slick pseudo-celebrity hotel for tourists. Milo has checked in under the name Emmanuel Goldstein, after the character in 1984. Few British journalists recover from George Orwell. Milo is very tall, handsome, and broad in the shoulder. He speaks in a strange combination of British and Miami. He greets me as a potential collaborator and friend. It is his instrument of seduction.
I was in New York to report on his attempted comeback after a spring when he fell, swiftly and dramatically, down a hole. A few months earlier, a recording was released in which Milo appeared to endorse sex between “younger boys and older men (the age of consent was not, he said, “this black-and-white thing”), and he was dropped first by his publishers Simon & Schuster, then by his employer Breitbart. He was disinvited from the Conservative Political Action Conference.
But I have yet to see him vexed by any drama, because Milo has played this game all his life. You could call it his safe space. We meet again in London in October, and he is cheerful, rushing off to see Wicked! as his career continues to crash around his ears. I couldn’t tell if he cared desperately, or not at all.
In New York, in June, the hotel room is filled with overflowing suitcases of clothes. The first thing he tells me is that he has just had $25,000 worth of AirSculpt on his abdomen, to make it smaller, because being fat is his worst fear. There is a fat man inside Milo, like the villain in Dodgeball, and the bill will eventually rise to $100,000. He had invited me to watch the procedure but I said I could not interview a sedated man.
We drive to the Trump International Hotel and Tower at Columbus Circle, where there is a generic rich-person restaurant on the ground floor. It is not busy; New Yorkers hate Trump and will not digest for his benefit. Milo chides me for my clothes, specifically my flip-flops. He has a very clear philosophy on how women should dress. He thinks they should dress like Nancy Reagan, or the Queen of England.
“I was never really worried about my career,” he says, speaking like a publicist describing a client. “Take a few months out, a dignified break to rest from the drama and let people stop being angry about nothing. They landed one on me and I took it as graciously as I could. Now I’m roaring back.”
When he talks about Dangerous, he sounds mad. “This isn’t the biggest book of the year,” he says, “this is the biggest book of the decade – if they saw it through. Maybe the most influential conservative polemic of the half century.” His editor at Simon & Schuster didn’t think so, describing it as “a superficial work full of incendiary jokes with no coherent or sophisticated analysis of political issues”. After they cancelled the book, Milo sued them for $10m, then changed his mind and didn’t.
Meanwhile, he says, he has outgrown Breitbart: “It is not a star factory. I was outgrowing the masthead.” He is in denial about why he is hated. “Sarah Silverman has said worse stuff about Jews,” he says. “Joan Rivers said worse stuff about everyone. I haven’t really said anything that awful. The thing I’m most closely associated with is ‘Feminism is Cancer’, which isn’t even an insult.” He chews. “It’s an internet meme.” This was a 2013 Twitter poll in which he asked, would you rather your child had feminism or cancer? “22,000 people voted,” he says happily, “and cancer won!”
I ask him to imagine he has a child with cancer. He can’t do it. “Cancer, yeah,” he says, “Cancer is curable,” because he doesn’t understand cancer. “Feminism,” he ponders, “you could be the walking dead your whole life.” He doesn’t understand feminism, either.
When opposed, he collapses easily. For instance, he says he is against abortion in all instances. I name an obvious case – a baby who would die – and he changes his mind. Then I ask: second wave feminism or pancreatic cancer? I have told him that pancreatic cancer is very dangerous. “The second wave, no question,” he says. The feminism is cancer meme made him famous, and he didn’t even mean it.
We leave the restaurant and walk south. Milo says hello to a man who I see only as a passing smile: “That’s my old hairdresser. He does Eric Trump.” He says there are 30 cats named after him, and 50 dogs, and a baby. He is happy with his hair and spends $1000 a month on it – “this is the best hair I have ever had, I think I am very handsome” – but he needs a new mouth: “My teeth are OK by British standards, but if I want to be an American star I have to spend $100,000 and get proper teeth.” We go to the hairdresser and then the dentist – a celebrity dentist with a photograph of Sylvester Stallone on the wall. If he gets dental implants, he says, I can live-stream them. He puts on his scarf. He looks surprisingly like a woman, and I tell him so. He doesn’t mind. He doesn’t mind anything, if it is about him.
Milo Yiannopoulos arrived in the US in 2016, as technology editor at Breitbart, after a dramatic career in British journalism. He was employed by Steve Bannon, who saw in Milo a “superstar” who could mobilise the right-wing youth and create a coalition that would propel Donald Trump, or a similar vessel, to victory. Milo’s job was to test the boundaries of discourse; how far could he go? Milo really loves Trump; that is heartfelt. He calls him Daddy.
He is gay and claims to be one quarter Jewish on his mother’s side, although he can provide no evidence of Jewish ancestry (I asked, repeatedly). Even so, both are valuable tools in identity culture wars. “Drop your toys, pick up your tools, and go help save western civilisation,” Bannon wrote to him, in an email leaked last year to BuzzFeed. “U r Social Media and they have made it a powerful weapon of war.”
Milo does not deny the emails are authentic. He simply says: “We don’t comment on stolen material”.
In 2016 Milo embarked on a travelling roadshow called the Dangerous Faggot Tour. He counted his fame in counter-protests and newsprint. After he was fired from Breitbart, Milo Inc was born. When we spoke in October last year, Milo said he and Bannon were still in touch.
The following day I collect Milo from the W and we walk to his gig on the Bernie and Sid WABC radio show. Bernie and Sid are bald and immense. “The great Milo Yiannopolous!” says Sid, who is the slightly larger, noisier one. “The fabulous Milo!” They congratulate him on Dangerous. “It means, the bitch is back!” says Sid, thrilled to be calling a gay man “bitch”. “You are more beloved, revered than you ever were!” Milo says he is hosting a Coming Out Conservative party as his drag queen alter ego, Ivana Wall (“I want a wall”).
“I get it!” says Sid, “Lesbians hate you,” he adds. “With some justification,” says Milo, “because I’m so rude about them.” Who do you like less, asks Sid, lesbians – or Isis? “Oh God,” Milo replies, and giggles, but he doesn’t answer. Sid asks: “It’s a brain twister? Really, it’s worthy of consideration?” “Of course, it is!” Milo shouts: “Isis is just the Middle East eating itself which has been the case since the dawn of time!” “Don’t lesbians eat themselves, too?” asks Sid. “Good heavens,” says Milo, lapsing into British coyness.
“Your tour was called the Dangerous – what rhymes with maggot? – tour,” says Sid, dazzled by his own rhyme. “The Dangerous Faggot Tour,” says Milo. He seems slightly annoyed. He doesn’t want to be a dangerous maggot, but he can hardly accuse Sid of homophobia. “Dangerous Faggot was more about identity politics for the college tour,” says Milo. “Dangerous puts the focus on free speech and censorship.” They talk about how ugly left-wing women are. “They have that disease that democratic women have where they think it is a virtue to be ugly,” says Milo. “I’ve never understood it. You go to the Republican National Convention and everyone is size zero in a beautiful little skirt and I think, ‘My goodness, I’ve gone to gay heaven!’”
During the break Sid says: “I have friends in Brooklyn” – and he lowers his voice – “I’ll be honest, they don’t like gay guys. But they love him,” nodding to Milo. “I’m gay but not I’m a prick,” shouts Milo obediently, in an American accent. “I’m not a fucking fag constantly whining and demanding to get attention and dressing up in pink feather boas”. He remembers that he does dress up in feather boas, but “I do it to make a point with a smile on my face”. “But you appeal to both,” says Sid, sounding amazed again. Milo did as Bannon bid him. He bridged the gap.
Bernie is the serious one. “Daddy, as you call him,” says Bernie, “was fantastic last night back on the stump in Iowa.” “It’s nice when you get a taste of it again, isn’t it?” says Milo. “The only thing I wanted from a Trump presidency was the complete extinction of political correctness in America. It’s a thirty-year project which I will now take up and,” – now I imagine him as a Spartan at Thermopylae but with a teddy bear – “complete for Daddy.”
I then watch Milo on the Anthony Cumia radio show, during which, to please an older, presumably brutal, straight man – another potential Daddy – Milo imagines he is straight. “I exclusively date white chicks,” says Cumia, “I love white trash girls”.
“Ooh, me too” says Milo. This is his most intense mirroring of straight right-wing men so far. “That’s what I would fuck”.
“The bleached blonde, the halter top and shorts, and just bruises on their legs,” says Cumia. “I love that shit”.
“Dukes of Hazard and downwards,” says Milo. “If I were straight I would like two kinds of girls. I would like big busted Latinos – and nothing as classy as J-Lo – and trashy Miami girls”.
“Just trash,” says Cumia. He does love bruises.
“And skinny fake tit blonde bitches like Pammy [Anderson],” says Milo.
“Barefoot out of their trailer,” says Cumia, and gives a moan from his solar plexus. “I love that”.
“Yes,” screams Milo. I think he can imagine himself into almost anything; that is why he rose, and that is why he fell. I think he led a political movement by mistake; but he would call me naïve and say the world I look to doesn’t exist anymore.
On Wednesday I meet him at a jewellery shop downtown. He has his fingers in trays of rings and seems remote: “I’m going to have a wedding band on here.” Milo is planning his wedding to John, 33, a “sensitive, sweet, calm” African-American man “with an endless capacity to love”. They met in a bar in Fort Lauderdale and hugged so much that Milo felt he was “dying”, which is a strange way to describe intimacy. “I never felt the things that I saw in movies,” he says; now he has a lover, “I have never told a single lie to”.
His entourage is here: Alex Macris, the CEO of Milo Inc., a second-generation Greek immigrant who took the job because, he says, he and Milo “want to build a 360-degree multimedia company that reaches this vast audience of consumers that is being ignored by so much of the bicoastal media”. That sounds like a press release, but it is from his own mouth. I also meet Macris’ girlfriend Casey, a British glamour model with pink hair and tattoos; and a stylist called Sebastian Occhione, whom everyone calls Sea-bass. Like the fish. This is Trump’s America; you won’t be listened to unless you are beauty queen hot. At least, they believe that.
Sea-bass describes Milo’s clothes. “If it’s expensive-looking he’ll wear it, because it’s just how he is. I just dress him in shit I would wear. Literally.” “But can’t afford,” says Milo, who is half listening. Is there a name for Milo’s look? “Not really. He looks like Justin Bieber right now.”
We get in a limo, and Milo tells me about a fashion shoot he is planning “in fat drag with cats and ice-cream and piles of Lena Dunham and Amy Schumer books, alone and miserable like everyone else who listens to feminists”. He hates Amy Schumer because he wants what she has. I think Milo is really a stand-up comic seeking approval and then sabotaging himself, so he remains in control. “I’ll going to sell more books than her,” he says, but, in the end, he doesn’t.
They discuss plans for Milo Inc: a talk-show hosted by Milo; the launch of Dangerous; an appearance at Free Speech Week at University of California, Berkeley in September; a tour of Australia; world domination; merchandising. “We have no competition, the market is wide open, there are people desperate to throw money at us and I’m really talented,” says Milo.
He sounds strained; how does he convert his charisma into political power while having no real interest in politics? “I want eventually for this to become a talent factory where I’m incubating more Milos.” I imagine an endless line of Milos stretching from here to the apocalypse.
We go into Balmain, where Milo is treated like clean water during a typhoid epidemic scored by Disney. He tries on a green silk bomber jacket and peers at himself. He is at his most serious in front of mirrors; in the hairdresser’s the day before, I thought he was praying. He doesn’t like the bomber jacket. He takes it off and picks up another jacket which is covered with paste jewels.
Seabass is fretting. “I don’t like it,” he says, “You know when little kids get the colouring books and they don’t know how to properly colour so they just put all the colours in it? It just looks like that.”
They now have a conversation so insane I type it out in full.
Milo: “What’s the final price on this? Is it $16,000 or $12,000 or something? It started like $32,000 right?”
Salesman: “So like $13,000.”
Milo: “When he [Macris] comes back in here I will try it on for him and then he can decide”.
Salesman: “Are we wearing the proper attire for him to see it?”
Milo: “It will be fine.”
Milo: “They will give it to me half off and we can have it mailed so we can skip the tax so it will be something like 13/14 [thousand dollars].”
Salesman: “Only one in the world”.
Milo: “It’s a complete one off”.
Macris: “Put it on let’s see”.
Milo: “I think Dad’s persuadable”.
Me: “You’re Dad?”
Macris: “I’m Dad”.
Macris [To Milo]: “It fits you like it was made for you”.
Salesman: “It was made for him”.
Milo: “This is why I’m considering it. I could have been measured for this”.
Macris: “That is definitely a wardrobe item for a tour”.
Milo: “I can just walk out on stage and be what – this old thing? OK I want it. Can I have it?”
Macris: “Yeah we can get it”. He swells, like a proud father.
Me: “Do you get the hanger?”
Milo: “I don’t think so”.
Later, in my bedroom, I receive a series of texts. They are copies of credit card receipts for the monstrous jacket, so I will believe that he really bought it.
In a fusty pink room in Chelsea, Milo is made into a woman. He wears a red and black dress. He is silent, transported somewhere I cannot reach. Miss Veronica Vera is the Dean of Miss Vera’s Finishing School for Boys Who Want to be Girls. “We weren’t sure,” she says, “if he wanted to go very over the top big bouffant drag queen look. That was what I was told initially. But when we got here we decided that he wanted to be more real – and pretty.
“This look is festive because Milo’s femme self – who we will call for now Mila – will be hosting a party. It’s a long gown and it’s kind of a combination of a gothic look but it’s also very kind of Miss Kitty dance hall girl look. Mila sees herself as a curvy girl so we have built in curves”.
Finally he speaks. “It’s fantastic”, he says, “There’s enough bad girl in there, isn’t there?” There is, yes; he looks like he’d do anything. I ask him if he feels different. “Not really,” he says, “but I live my whole life in character.” I think that is the second most truthful thing he has told me. He climbs down from the mirror and sashays towards me. He has added a red ribbon to his wig and looks like a ruined Dorothy Gale. He looks like his mother.
The Coming Out Conservative party is in a greasy club uptown. We are very early. Milo takes off his wig, sits down in a curtained-off VIP area, and drinks champagne through a straw. His manager Jeanette administers a Vitamin C spray because, she says, “if he gets sick we all get sick”. The king and the land are one. She fans him while the PR team iron a Dangerous sign. He is calmer, more serious, and more likeable as a woman.
I ask if feels responsibility for the behaviour of his supporters: for the abuse of the actress Leslie Jones on Twitter, which got him permanently barred (he called her “a black dude”). He says it is the left who protest violently at his events. “I get asked, am I mean and cruel and vindictive?” he says. “Meanwhile [the comic] Kathy Griffin is the one with Trump’s bloody head [in a video]. Get your own house in order before you come and talk to me about shit. I’m an artist and I’m going to create provocative, dangerous things. I’m not the one standing up with a decapitated head. I could have done that to Leslie Jones. It wouldn’t even occur,” – and the “occur” is totally aghast – “to me”. This is the closest I will come to thinking there is something decent inside Milo but it flees and he is someone else again.
Milo walks to the top of the stairs in sunglasses. He is carrying a bottle of champagne, a glass, and a microphone. I think he is drunk. “We are here,” he says – and he lowers his voice – “because we don’t think that just because you like sucking dick you have to give up God, or guns!” He doesn’t have a gun. He told me he isn’t allowed one, because he is British. “We are here because the oppressive, corporatised, fucking boredom of the mainstream extreme progressive Left Pride movement does not represent the fun, mischievous, dissident magic that made the gay community so fantastic in the first place!” A woman shouts: “Amen!”
“You are here,” he says, “because, like me, you recognise that there is something a bit more at stake than transgender pronouns in America today for gay men – and lesbians”. A woman shouts: “Feminism is cancer!” “Did anybody in this room read the Washington Post’s account of the Pulse nightclub shooting this week?” he asks. A man shouts: “Fuck WashPo!” “Could you have a wild guess how many times the Washington Post report about the shooting in the Pulse nightclub in Orlando mentioned any of the following words: Muslim; Islam; terrorism?” “Null,” says a man. He wins a glass of champagne.
They start shouting: “Build the wall! Build the wall!” Then: “Lock her up!” I can’t tell if they are joking. When they stop, Milo shouts, “We are gay! We should be pushing every conceivable boundary. We’re not all idiots who turn up on a Saturday night for attention in a wig”. He tosses his wig. “Sipping through a straw”. He sips champagne from a straw. “Lolloping around in fake tits. That’s not all of us! Please give it up for the end of political correctness, the end of political correctness – and coming out conservative!”
He poses for selfies with a succession of nerds and gay conservatives. I meet a man who is afraid to tell his colleagues he voted for Trump and a man who came out as conservative and lost 500 Facebook friends. They are not all monsters but some are very stupid. I meet a female journalist who asks me what feminism has done for her. Everything, I tell her.
On the last day we go to the Palm Court at the Plaza Hotel, because Milo once cried when he watched a movie called Bride Wars, in which two small girls have tea at the Plaza, and, as adults, fight over the same wedding slot at the Plaza. Bride Wars is about how the desire for attention cannot thwart true love. I’m not surprised he cried.
The day before, he had emailed his mother a photograph of himself as Ivana Wall. “They put me in drag today,” he writes, “I look like a circus version of you.” She replied a day later: “That’s not not a good look”.
Much of his rage seems directed at his mother, Karen Latham. She divorced his father when Milo was five; his stepfather resented his existence; his father Nicholas, though protective, offered no security. He had not, then, spoken to either of his parents for over a year: “I don’t feel anything about it, I don’t think about it. When I was growing up I thought I was a sociopath. Now I realise I am capable of great depth of feeling, but I have certain bits of my brain missing: getting offended; getting ashamed; and getting afraid”.
He says he was sexually abused by a priest when he was 12, or 13, although his critics say he invented this to excuse his comments on paedophilia. He is anxious when I ask him about this, but pretends he isn’t: “I will inform the nice people at the Plaza about my priestly dick sucking,” he says. And he does, while eating. He went to mass “infrequently”. Then he says: “Did I make a mess?” He is worried about the scone crumbs. “I think I did. Sorry. There was Father Michael at that time who,” – he pauses – “I never had penetrative sex with. I used to hang out in church a lot, and read, so I didn’t have to be at home with any of them.” He notices an individually wrapped cube of sugar: “That is garbage. Fuck off, America”.
He enquired about the priest, “and my understanding is that he is dead. I saw the name and saw that he died and somehow closed the page. Is that a bee? I saw something, do you see it?” I don’t see the bee. I don’t know if this story is true, and it is barely relevant. It is a founding myth, explaining everything that comes after. He eats another sandwich. “I know there are people for whom this is the worst thing that has ever happened. I just don’t feel that way”.
He wants to talk about Trump instead; the consolation of Daddy, a man who makes him feel safe. He has met him only once, after a rally in San Diego, and he thinks Trump has as much charisma as Mariah Carey, which is a typical Milo sentence. “He’s perfect,” he says, “the most charismatic person I’ve ever met. Trump has done what I want to do. He has taken over the fucking world. He has his name stamped on buildings on every continent.”
He takes another sandwich. “I spent thirty years powerless and dependent and miserable and alone, and then I discovered that I had this hold over other people. And if I only attached that to a worthwhile, noble cause then I could adjust the course of history.” He says he is “one of seven people who put Trump in the White House”. The seven people “maybe” includes Trump himself.
But what is it all for? He doesn’t know, and so he places himself outside the question. “I’ve never really heard anyone answer that question convincingly. Some of us are just broken in that way.” He fumbles for more, and lands on Madonna: “Has anyone ever asked Madonna, ‘I get it, you want to conquer the world – but why?’ I don’t recall her being asked that.”
I try to draw him on his politics, and ask him about the cuts to Medicaid, which he supports. He is angry: “It’s so boring! … I’m not a political pundit. I don’t know why people ask me about this shit.” This is his flaw as a political activist, and the reason he fell. He doesn’t know much and, worse, he doesn’t want to.
I am exhausted by him and go I home to England. But I follow his adventures. Berkeley didn’t burn during Free Speech Week. Trump tweeted, obliquely, that Milo should be allowed to perform but the university simply denied him a microphone and wouldn’t let fans in to the plaza, where he posed for selfies with about 30 people.
He was mobbed in Australia – he sold out 1,200 seat venues – as well as denounced, so it was a partial success. He did marry John, in the Four Seasons Hotel in Hawaii, in ludicrous clothing. The wedding, he tells me, cost $300,000, and 12 guests, “ate for four days”. His mother came, and he bought her a $7,000 hand-bag, which made her “happier”. He also got 12 veneers on his teeth and promoted the 30-Day Liver Cleanse supplement on Infowars, to much derision.
In October BuzzFeed exposed his closeness to Steve Bannon, and the funding of Milo Inc by the Mercer Family, just as it was ending. They also said that he once used the password Kristallnacht for a joke.
I telephone him in Miami to ask if this is true and he says yes, instantly. After all this time, I wonder why he doesn’t lie to me. And then he says, and this is the most truthful thing he has said to me, though he says it calculatingly and without self-pity: “I’m drawn to the darkness. I’ve always been drawn to the darkness.”
We speak again in January. He texts that he has new funding and there will be a tour with a “left-wing celebrity” this year. “I’m going to have a career that last decades,” he says, “People love me everywhere. It was a tumultuous 2017 but everyone who put Trump in the White House got punished somehow. It’s what happens after elections.”
We speak again a few weeks ago. He has a new strategy, he says, because new media wants to destroy him: “We made a mistake handing over our distribution to people who want to exterminate us,” he says. “Personalities like me are being strangled to death by Facebook and YouTube and Google and Twitter. I have millions of fans worldwide. But they can’t get my stuff”. And so he is “returning to traditional distribution. The business of being somebody like me is a going to become a lot more like being a political party where you have a massive email database”. He has a subscription-only talk show and has also founded a new charity called the Freedom Action Group, or FAG. The right, he predicts, will disappear from view, and return only to win elections.
“I am more popular than I have ever been before,” he says, “but there are no external physical signs of that”. I hear not the ghost of a grin.