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How Much Longer Can the Milo Yiannopoulos Show Last?

Milo has carved out a safe space for his politically incorrect views. But he’s also basically a failed artist.
milo yiannopoulos by emily traynor

In late December, alt-right enfant terrible Milo Yiannopoulos signed a book deal with Simon & Schuster that included a $250,000 advance. The news angered many people, prompting some critics and publications to declare that they would not review Simon & Schuster’s 2017 catalog. Writer Roxane Gay, upon realizing that she and Milo now shared a publisher, ordered her agent to withdraw her book prior to publication. Other commentators, such as Alexandra Schwartz at The New Yorker, responded by noting that Yiannopoulos, while guilty of “opportunistic hate-mongering,” is merely the latest among dozens of conservative writers whose guaranteed sales numbers already help a profit-driven publishing industry stay afloat.

So there we have it: another victory for one of this season’s most conspicuous bad boys, a self-proclaimed “dangerous faggot” who uses his bully pulpit on Breitbart to castigate “Islamofascists,” “cancerous” feminists, and anyone who thinks that certain video games are violent and misogynistic. Yiannopoulos’ success came simply because he hung on long enough, evolving his views on issues like video games (which he once derided as vapid entertainment for simple-minded boys) in tune with the emerging alt-right movement, to secure his place in that market. And his ongoing “Dangerous Faggot”college tour has galvanized both his staunchest opponents and strongest supporters, leading to plenty of tense and attention-grabbing confrontations between him and progressive students who don’t like what he has to say — most recently in the form of violent protests at the University of California–Berkeley that prompted Yiannopoulos to cancel his talk there.

Last September, people rushed to criticize Out magazine for publishing a profile of Yiannopoulos that many viewed as a puffy and insubstantial — in other words, normalizing. Today, for many progressive journalists mulling the ethics of Yiannopoulos coverage, the issue had ceased to be about the propriety of whether or not to cover him; we have long since passed the point of no return. Yiannopoulos is, after all, a rich subject, a bug zapper attracting freelancers of every political stripe. Instead of a gag order or a media blackout, the impulse now among most mainstream journalists is merely to cover Yiannopoulos without conferring on him the kind of legitimacy that leads to a full-time gig hosting a Fox News show.

But this has proved no easy balance, when it comes time to write the profile. Like so many politically astute Bad Boys of yore, Yiannopoulos is “utterly charming,” as Kristen Brown notes in an essay about him for Fusion. I know this firsthand, having appeared on a BBC radio program in which Yiannopoulos charmed the pants off host David Aaronovitch and Newsday contributor Cathy Young. He dominated the conversation, hammered his talking points about the gradual mainstreaming of the alt-right, and more or less carried on like a whimsically deconstructed version of urbane conservative gadfly William F. Buckley, updated and rebranded for the age of identity politics.

Yiannopoulos is merely a flamboyant artist manqué. Dangerous, the title of his forthcoming book with Simon & Schuster, seems intended mainly as self-reassurance.

Buckley, aside from outlier moments like his testy, expletive-laced 1968 showdown with Gore Vidal, was the epitome of cool, go-fuck-yourself, uncompassionate conservatism. He wasn’t a Bad Boy in the Marlon Brando-in-a-leather-jacket sense, of course, but rather an unabashed elitist who could say truly dreadful things — things Hannibal Lecter or Lex Luthor might say — while beaming at crowds that sometimes despised him (“The death of Saddam Hussein at rope’s end brings a pleasure that is undeniable,” he once wrote). I became enamored with his style during high school, when I read my father’s copy of The Unmaking of a Mayor, which detailed Buckley’s unsuccessful 1965 campaign for mayor of New York against then-Republican John Lindsay, who later defected to the Democratic Party. The book was full of Buckley’s trademark bons mots and detailed how Lindsay’s operatives had attempted to smear him as a latter-day Nazi (an insult later utilized to great effect by Vidal, and more recently directed against Yiannopoulos).

My brief infatuation with Buckley ended after finishing his book God and Man at Yale and watching several hours of old Firing Lineepisodes on VHS. WFB’s shtick, I had found, was polished but limited in scope: He wanted to fight the “Reds,” he had tremendous disdain for democracy and the general public, he worshiped at the altar of Western Civilization and the Roman Catholic Church that (he said) had sustained it, he opposed far-reaching federal legislation like the Civil Rights Act, and he didn’t believe rich people should be taxed at those high, 1970s-era rates. He made these points over and over, always with a wink and a smile, always while seated cross-legged, half-asleep in that gloriously elitist prep-school manner of his — and somehow he retained a national audience for the better part of four decades.

Perhaps it’s not so hard to understand why he lasted until the bitter end: Buckley might have been outrageous and cold-hearted, but he wasn’t horrifying, at least not to certain intellectual taste-leaders, some of whom shared his lust for lower taxes. He wasn’t a win-at-all costs muckraker like Emmett Tyrell Jr. of The American Spectator; he wasn’t a lunatic conspiracist in the style of John Birch Society founder Robert Welch; he wasn’t a gauchely overt racist on the order of populist presidential candidate George Wallace. He might’ve been a Bad Boy who trafficked in politely naughty jokes, functioning alcoholism, and quips about the “booboisie,” but, at the end of the day, he was also the sort of hail-fellow-well-met you could go yachting with.

Like Buckley, Yiannopoulos appears similarly reasonable and approachable among today’s conservative Bad Boys, particularly among those swarming his alt-right camp. Just consider the competition: Alex Jones boasts an enormous and passionate fan base, but he’ll never be a thinkfluencer among the highbrows as long as he’s engaging in histrionic prophecies about lizard men and the Antichrist. Richard Spencer, with a haircut borrowed from Peaky Blindersand an ideology that’s warmed-over neo-Nazism by way of Duke University’s history department, is an avowed white supremacist. Mike Cernovich is testosterone test-addicted self-help guru who says he’s hard at work developing “Gorilla Mind” nootropics to enhance your understanding of his Gorilla Mindset manifesto (quick tip: stand and breathe like a gorilla). And then you have a host of lesser figures on the order of rape apologist Roosh V, who emerged out of the seedy underground of pick-up artists and men’s rights activists.

Yiannopoulos, meanwhile, is merely a flamboyant artist manqué: He grew up wanting to be a theater critic, and today leavens his political commentary with bizarre stunts such as bathing in blood and addressing university crowds while hidden beneath a burqa. He is polished, poised, and oddly non-threatening behind all the exaggerated rhetoric (he even got trolled by Nazi readers of The Daily Stormer when he denounced anti-Semitic elements on the alt-right). Dangerous, the title of his forthcoming book with Simon & Schuster, seems intended mainly as self-reassurance. For commentators sympathetic to some of Yiannopoulos’ aims, the deliberateness behind his provocations surely comes as a relief. In the eyes of these observers, there are two Milos: Yiannopoulos the person is a serious-minded activist who wants to save Western Civilization (just as the 20th-century creators of that curriculum intended!), while Yiannopoulos the character is a vulgar clown, a pro-wrestling heel who gleefully performs the outrageous skits needed to galvanize his audiences into action.

Rachel Fulton Brown, a professor of medieval history at the University of Chicago, has written extensively about this aspect of Yiannopoulos’ character. “Milo is playing a particular kind of role: that of the holy fool,” she writes in an email. “He is a clown — like St. Francis of Assisi — using jokes to shock us out of our established pieties. Like Francis, people find him outrageous and embarrassing: If Francis stripped off all his clothes in the piazza of Assisi to shock the wealthy elite of his hometown, Milo has dressed in drag, had himself ‘hazed,’ disguised himself as a protester at one of his own talks, dressed in police fetish gear carrying a giant pink dildo water bottle, and had himself carried into the lecture hall on a golden throne. He wants to shock people out of their complacency and make them think, but like Francis, he does so by making himself a figure of fun.”

Fulton Brown, an outspoken defender of the European intellectual tradition against relativism and multiculturalism, believes Yiannopoulos has used his Bad Boy persona to pose serious questions about the long-term survival of the West. “He sees himself as a vanguard, particularly with his campus tour: He knows that he is a joker, not a professor, but he wants us professors to wake up and start teaching facts — real history, not fake history, real philosophy, not fake philosophy,” she writes. “I have been as impressed by the students in his audiences as I have been by his talks. I can tell that his fans want to learn more about the things he is saying, but often his talks are the first time they have heard any of it.”

In Fulton Brown’s opinion, Yiannopoulos’ calculated buffoonery is the reason people stick around to listen to the substance of his remarks. For her: “Milo’s story is as much about the reasons that the students like him as it is about him. If you want to write about him accurately, you should watch some of his campus talks and watch the audiences: what they mainly feel is relief at being able to laugh again.”

Like Buckley, Yiannopoulos can command an audience. Neither man would be at home with the pitchfork-wielding Tea Party hordes — at least, not so effectively as prime-period, pre-redemption tour Glenn Beck, say. Buckley and Yiannopoulos have a different sort of mass appeal, a suave, effete Bad Boy style more suited to Bond villains than to members of Batman’s rogue’s gallery. For Buckley and Yiannopoulos, that persona has served a very specific social purpose.

Fulton Brown’s views are not broadly representative of medieval scholars. Dorothy Kim, a literature professor at Vassar College and author of Digital Whiteness and Medieval Studies, has written about the politics of digital space and takes a dim view of Yiannopoulos, whom she views as a dangerous troll. “Milo is a joker, but he uses a form of ‘executioner’s humor.’ He is supporting and upholding violent white supremacy, racism, and anti-feminism,” she says. “And yes, I’m sure his supporters are right: His audiences do feel relief at being able to laugh again — because they want to be able to deploy ‘executioner’s humor’ to display their racism, sexism, ableism, queer-bashing, transmisogyny, anti-Semitism without pushback. This is the hallmark of neo-Nazis, white nationalists, and white supremacists.”

For Kim, who has battled back and forth with #GamerGate and alt-right trolls, Yiannopoulos’ popularity provides an opportunity to expose and oppose the bigots who have cast their lot with him: “How much have virulent antisemitism, sexism, racism, transmisogyny, ableism, queer bashing become part of our nation’s everyday fabric? How much have words translated into violent action? The Southern Poverty Law Center tries to keep track of the hate crimes: The statistics for 2016 have been staggering and the numbers post-election astronomical,” Kim says. “I have seen too many of my colleagues attacked to think Milo is in any way funny. We should call his behavior what it is. Violence.”

And what does Kim make of the comparison of Yiannopoulos to St. Francis, that holiest of Bad Boys who once ordered a friar who had handled money to take the offensive coin in his mouth and place it on a pile of donkey dung?

She answers with an anecdote: “In 1219, St. Francis waltzed into Sultan al-Malik al-Kâmil’s court and proceeded to preach to them expecting one of two outcomes, as patterned off of all martyr saints’ lives dealing with heathens. Either his preaching would miraculously convert them all or they would kill him and he would instantly become a saintly martyr. Neither happened. The court just asked him to leave.”

*Update—April 25th, 2018: This article has been updated to correct the spelling of the subject’s name.