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Perhaps the most shocking thing about Milo Yiannopoulos is that he is utterly charming.

Online, the 31-year-old conservative Breitbart columnist is the sort of frustrating troll who, for instance, might declare his birthday World Patriarchy Day, suggest Donald Trump is “blacker” than Barack Obama, or, although he is gay himself, assert that gay rights have “made us dumber.”

He was recently booted from a demonstration against sexual violence in Los Angeles after showing up with a sign that read “‘Rape culture’ and Harry Potter. Both fantasy.” A dedicated contrarian, Yiannopoulos seems to delight in making enemies.


But in real life — in spite of all this, or, perhaps, because of it — Yiannopoulos is disarmingly likeable. After all, you don't amass 85,000 Twitter followers, become the conservative torch-bearer in a gaming industry civil war, attract a cult following among young, Internet-savvy men, and become a figurehead of the Men's Rights movement without knowing a little something about exploiting the human psyche.

When I meet him in San Francisco, a few days after the aforementioned demonstration, he greets me as if we’re old friends.


“Hello darling, how are you!” he exclaims, offering a hug. Yiannopoulos, who lives in London, was once described as a cross between a “pitbull and Oscar Wilde.” It’s barely noon on a Monday, and he and a friend are drinking in a dark bar in the Lower Haight, already onto their second glass of rosé. He had ordered me a glass. Wearing his signature aviators indoors, leisure shorts, white plastic flip-flops and a t-shirt reading #REPUBLICAN in gold foil lettering, Yiannopoulos looks slightly hung over.

We discuss his favorite American president (Calvin Coolidge, for his wit), George W. Bush (“incredibly sexy in person”), his belief that there are fewer transgender men than women (“women don’t care to become men”) and his searing hatred of third-wave feminism, which Yiannopoulos characterizes, generally, as a mob of bitter man-haters railing against institutional injustices like the wage gap that no longer actually exist.


“I would be a second wave feminist,” he says. “I believe in equal opportunities for women, but if they don’t choose to work as hard, they don’t get rewarded.”

“I don’t think you know what feminism means,” responds his drinking companion, a liberal lawyer, who tells me that she blocked Yiannopoulos on Facebook because she sometimes finds his columns so infuriating. This, it turns out, is common sentiment among many of his friends.


“I just can’t believe you’re anti-feminist!” she tells him.

“I would never describe myself that way,” he responds, launching into a much-rehearsed soliloquy. “There is a specific brand of feminism that is destructive and I think it is driving men and women apart. I hate it. It makes everybody miserable.”


Their friendship survives, she explains, because they generally agree not to discuss topics like politics.

“People have this idea that I’m a misogynistic monster,” Yiannopoulos tells me, “But as soon as they meet me they say, ‘Oh, you’re so nice in person!”



Milo Yiannopoulos has been a divisive figure in the London media scene for years, but with the emergence of the Gamergate movement last year, he became an unlikely mouthpiece for the U.S. conservative movement.



It's been just over a year since an online rant by the disgruntled ex-boyfriend of female video game developer Zoe Quinn set off a brutish culture war in the gaming industry. On one side was a diverse set of gamers who didn't identify with the stereotypical nerdy white guy that games seemed to be designed for with their heavily-muscled protagonists and scantily-clad female set pieces. On the other were mostly male gamers who rallied around the hashtag Gamergate, alleging that collusion among feminists, progressives and journalists was changing gaming culture for the worse.


In most media outlets, stories about Gamergate focused on the harassment campaigns the movement launched against Quinn and other prominent women in the gaming industry. Yiannopoulos, though, took up the Gamergate cause, publishing a story headlined, “Feminist bullies are tearing the videogame industry apart.”

“An army of sociopathic feminist programmers and campaigners, abetted by achingly politically correct American tech bloggers, are terrorising the entire community – lying, bullying and manipulating their way around the internet for profit and attention,” he wrote, in what would become the first of many pro-Gamergate pieces.


For Yiannopoulos, the consummate cultural libertarian, GamerGate had it all. Angry feminists! PC police! Ideological left-wing journalists! Drama!

“I always thought journalism was about sticking up for the many against the powerful few,” Yiannopoulos told me. “There aren’t many people who would stick up for an odd guy with no money who lives in Wisconsin, hates his wife, plays video games to escape from his miserable life and is suddenly told that just because he likes playing Grand Theft Auto he is a sexist misogynist pig. I feel for that guy.”


Yiannopoulos lent Gamergate's weird corner of the Internet an air of mainstream legitimacy.

“He’s been the only journalist so far to give Gamergate any sort of credibility,” said Alex Baldwin, a 23-year-old former moderator of the Gamergate subreddit KotakuInAction. “Without Milo, it probably would have just fizzled out, in all honesty.”


One anti-Gamergate activist who wished not to be named told me that his effect in amplifying the movement was “inestimable.”

“He is its only legitimate face,” she said. “He gave the movement a platform.”

In turn, Gamergate elevated the influence of Yiannopoulos. He immediately became a cult hero, the subject of hundreds of obsessive tweets and fan art, and even a character in a video game, Postal 2.


With snarky headlines, theatrics and sarcasm, Yiannopoulos had figured out how to make conservatism go viral. A video posted to Breitbart of Yiannopoulos getting thrown out of that L.A. demonstration attracted nearly 2,000 Facebook shares and as many comments. Another recent story titled "Sexbots: why women should panic," was shared on Facebook 15,000 times. For context, the median number of Facebook likes and shares for The New York Times' most-shared columnist, Nicholas Kristof, is about 2,400.

Yiannopoulos' editor, Alex Marlow, told me that the Gamergate coverage has infused Breitbart's demographics with a new, younger audience. This fall, Breitbart is planning to unveil a new section focused on tech and gaming, with Yiannopoulos at the center.


“Milo has an ability to resonate with younger people that is uncommon in the conservative movement at this time,” Marlow told me. “Conservatives have made a mistake in ignoring youth culture.”


At 6’2, punctuated by a tall poof of bleached hair, Yiannopoulos' real life presence feels as big as his online one. In person, his friends will tell you, he is always "on," whether he's railing against the matriarchy, bragging about his own fabulousness or discussing his love of “black dick.” He is a fearsome conversational opponent, quick to dispense the same sharp-tongued, irony-tinged wit that he does in writing whether the topic is Mariah Carey, of who he is a devoted fan, or feminism. Often you find yourself in a sparring match with Yiannopoulos without ever meaning to engage in one. For Yiannopoulos, any interaction is the opportunity for an audience.

“My natural disposition is a satirist and a comic,” he said, by way of explanation. “I like to entertain and to please people.”


Republican presidential hopeful Donald Trump is one of Yiannopoulos' idols and it's not a hard guess why: Trump has perfected the art of the political as the performative, of somehow channeling impolite chaos into charm. In Yiannopoulos, it seems impossible to separate the man from the mythology, and really it's not clear whether there is much separation anymore. Years ago, he tells me, he used to keep part of himself hidden away from public view, worried about whether others would like him.

"I didn't like me very much and so I created this comedy character," he says. "And now they’ve converged."


Yiannopoulos makes no attempt to disguise his love of his burgeoning celebrity.

"I could spend all day, everyday reading stuff people post about me on the Internet,” he says.


His social media presence is dizzy with selfies, fan art and bubbling champagne. When his lawyer friend wants to send a photo of their drinking damage to her boyfriend, Yiannopoulos rearranges the table, propping up his pack of Newport menthols and making sure all six of the empty glasses made it into the shot.

“I’m experienced at this,” he winked.

Frequently, critics aim to insult Yiannopoulos by calling him a troll, but troll is a role he is perfectly comfortable inhabiting. He views the roles of satirist and journalist as interchangeable (and often in his work it can be hard to tell which he is playing). Whether his extreme convictions are actually “real” is besides the point — though he will tell you that, most of the time, they are. His Twitter stream is full of retweets of nice things his fans say about him. But he retweets the mean things, too. His main goal is just to get under your skin.


“The only proper response to outrage culture is to be outrageous,” he told me, reciting a frequent Yiannopoulosism.

He grew up in a small town in Kent, living a middle class existence with his mother, architect stepfather, “horses, two cars and a pool" until eventually tense relationships with his parents moved him to go live with his grandmother as a teen. Like many a good conservative, he identifies as Catholic (although his mother is technically Jewish). His grandmother, whose weekly e-mails he turned into a Tumblr page, was an outsized presence in his life and the most accepting when he eventually came out as gay. He dropped out of university twice and never finished, a fact of which he claims to be extremely proud.


His first big writing break was at The Telegraph. Even back in 2009 his stories — with headlines like “Men perform better in many technology jobs. Must we apologise for that?” — relied on much of the same rhetoric typical of Yiannopoulos today.

Yiannopoulos had wanted to be a theater critic, but said he became drawn to tech after writing about the lack of women in the industry.


“Women have huge competitive advantage when they go into tech because there aren’t many other women. They get coverage when they don’t deserve it, when they enter a room, people pay attention to them. Privately successful women will tell you this,” he said. “It struck me as garbage. So I stayed in tech.”

The modern women’s movement is by far his greatest agitation and a source of constant preoccupation.


“Women’s rights is one of the great successes of our society. But it seemed like we were taking a retrograde step,” he told me. “We were going backwards. We were giving people like feminists podiums to bully people. A lot of what I have done since is purposely ridiculing that, getting under the skin of people I have decided are bigots.”

After parting ways with The Telegraph, Yiannopoulos co-founded the tech news and gossip website the Kernel, at age 28. In a profile of him at the time, The Guardian described him as “a man who collects enemies like carrier bags” for the incredible number of public spats he picked. To wit: in response to Twitter criticism from an English blogger calling Yiannopoulos a "sexist, misogynistic prick," he replied: "We write about how tech is changing the world around us. You write about how many cocks you've sucked this week. Back off."


When former contributors pursued legal action against the Kernel for failing to pay them, The Guardian published threatening e-mails Yiannopoulos had sent to his unpaid former writers. In one, he threatened to unleash embarrassing photographs online. In another, he wrote: “You've already made yourself permanently unemployable in London with your hysterical, brainless tweeting, by behaving like a common prostitute and after starting a war with me, as perhaps you are now discovering.” (The Kernel eventually folded, but was then relaunched after Yiannopoulos settled debts personally and later sold to The Daily Dot.)

Few of Yiannopoulos’ critics would speak to me about him on the record and more than one warned me of the personal perils I might face in writing about him, a detail I’d wager he might find more flattering than anything else. Most described him as somewhat volatile, a man who can completely charm you and then turn on you just as easily.


“He has a spreadsheet of all of his friends and how much he likes them,” one friend and former employee, James Cook at Business Insider in London, told me. “If you’re on the top of the list, great; if not it’s terrifying.”

(Yiannopoulos has actually written about the list: “The spreadsheet is simply the best tool I’ve developed so far for managing an ever-increasing contact list of interesting people I am anxious to introduce to one another, or with whom I want to spend more time.”)


Another insult often lobbed at Yiannopoulos is that he is simply an opportunist, especially in relation to Gamergate, before which he had openly mocked video game culture. In one piece written in 2013, he derided gamers as “unemployed saddos living in their parents’ basements.”

Yiannopoulos addressed this criticism with a single tweet:

https://twitter.com/Nero/status/524302853846757379



But the funny thing is that Yiannopoulos actually still describes gamers that way. His fans just love him anyway.


"What I think they like about me is that I don't pander to them,” he says.

Alongside man-hating third-wave feminists, pandering is among the things that Yiannopoulos hates most.


“My style is take no prisoners," he said. "There’s nowhere I won't go.”


When I first wrote to Yiannopoulos, it was because I wanted to understand what made him tick. As an openly feminist journalist covering technology, I had written a lot about systemic biases against women plaguing Silicon Valley and the tech industry's fratty male culture. I was fascinated by the way Yiannopoulos would unpack those arguments, proposing, for example, that there are fewer women in the tech industry because they just aren't all that interested in tech.

"Here’s something you probably don’t know," he'd argue, "in countries like Pakistan and Bangladesh, the gender split in science courses at university can be as high as 50-50. But, when you look at more equal, enlightened societies such as Norway and Sweden, the number of women doing STEM subjects plummets and goes down every year relative to admissions."


Often his articles would send me into a tailspin, questioning whether what I knew was merely what I thought I knew. My reporting relied on studies that showed that women were dropping out of the tech industry in droves citing harassment, something I had personally experienced. But I also know that data lies. I wondered whether it was me or Yiannopoulos that was guilty of cherry-picking data points that proved what we believed to be true. Or maybe it was neither of us. Or both.

I also often found in his work surprising nuance, like the suggestion that women returning from time off to raise kids should get a salary bump to make up for raise opportunities they missed while at home.


Then I would get to the next paragraph, which might start something like this, and find myself enraged all over again: "women's brain's aren't as suited to programming as men's."

It's true that some studies have shown that male and female brains are wired differently, but still others have claimed that any difference is marginal. And regardless, we know far too little about the brain at this point to know definitively what makes someone good at programming.


I told Yiannopoulos about an experience early in my career, when a male editor asked me if I was crying because I was a girl and would therefore never make it as a journalist when in fact my eye was just watering because something was in it. As a young woman, this was an experience that opened my eyes to the sexism that persists in modern work environments. I remember being completely shocked.

“But women do cry!” he responded. “They cry more often than not. It’s not an unreasonable assumption. Journalism is very male and very aggressive and it can be difficult for women to survive.”


And it's true, science suggests that women do cry more, though for reasons that are far more complex than just overcharged emotions.

“These days we credit feeling over fact,” Yiannopoulos told me. “We have elevated discomfort to the level of serious injury. We seem to think that somebody feeling slighted is a great crime.”


Despite the fact that I am exactly the sort of feminist Yiannopoulos frequently rails against online, I found myself transfixed by him. After four hours and a move to a gay bar with a patio, I’d divulged the embarrassing details of my first kiss and he had somehow persuaded me to rethink a decades-long hatred of Mariah Carey. I remembered something Cook had told me, about how Yiannopoulos would often convince him of an argument during conversation, and only upon leaving he would snap out of it, and realize it was absurd.

"Everyone who knows Milo has been absolutely shocked by his rise," Cook, told me. "I think we’re all scared that one day he’s going to go a bit too far. It concerns me how easily people believe him."


To enter Yiannopoulos' world is to enter a world of topsy-turvy logic, after which you are never truly sure again of which way is up.

“I don’t share the preoccupations of the right that animate Milo’s anger,” said Jason Pontin, publisher of the MIT Technology Review, and an unlikely Yiannopoulos defender. “But for me, Milo pushes all the right buttons. He’s charming and witty and charismatic. A world where Milo writes the pieces he writes and flounces around with his fabulous hair is a better world for me. More speech is good.”


Another friend, Alicia Navarro, founder of Skimlinks, told me that while she doesn't always like it, Yiannopoulos "does put forward arguments that make us think."

And it's true. Yiannopoulos does make you think. Reading his work is a rush of questioning self-doubt, the kind I like to think that makes us all better, more rigorous thinkers. And because Yiannopoulos is an expert in the packaging, reading him is a bit like vinegar with coated honey, each acerbic bite encased in a flurry of "hello darlings" and champagne.


But it's a thought-experiment with potentially terrifying consequence.

Yiannopoulos is successful in part because he has tapped into very real cultural anxieties. He likes to say that he is the voice for a voiceless majority. Over and over, in letters and phone calls, his fans espoused their gratitude to him. "For giving people like me who feel like they have been irreparably damaged and abandoned by the majority of society a voice," said one. Or that he made them feel like "someone actually cared about them and understood their frustrations."


At Breitbart, his tens of thousands of disciples are only growing.

"I'm a Milo fan because I agree with everything he writes!" one female fan told me.


But not even Yiannopoulos agrees entirely with everything he writes.

"I don't write anything I don't believe," he told me via e-mail one day, "but I won't pretend I don't provoke on purpose, because of course I do!"


Yiannopoulos exists at the center of the kind of question Yiannopoulos himself would jump to answer. Is all free speech good speech, no matter the cost? Undoubtedly, he would answer, "Yes, darling."