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Donald Trump’s Little Boy Is a Gay Half-Jew With Jungle Fever

The sad story of Milo Yiannopoulos: the Trump troll with Daddy issues

James Kirchick
June 02, 2016
Photo: Justin Sullivan/Getty Images
Milo Yiannopoulos stops to take a picture after speaking during a free speech rally at U.C. Berkeley on September 24, 2017.Photo: Justin Sullivan/Getty Images
Photo: Justin Sullivan/Getty Images
Milo Yiannopoulos stops to take a picture after speaking during a free speech rally at U.C. Berkeley on September 24, 2017.Photo: Justin Sullivan/Getty Images

Milo Yiannopoulos is a fervent supporter of Donald Trump’s presidential campaign. Referring to Trump as “Daddy,” the ostentatiously gay British media personality provides a camp component to the presumptive Republican nominee’s fan base. What seems to excite Yiannopoulos about Trump is what seems to excite most of the tycoon’s voters: a brash, take-no-prisoners attitude. When I recently asked Yiannopoulos to name the Trump policies he favors, he replied with a very revealing answer. Trump supporters don’t care about the man’s policies, he said. “They want to burn everything down.” Suddenly Yiannopoulos’ Twitter handle, @Nero (followed by more than 200,000 Twitter users), made all the more sense.

Simultaneously vacuous and sinister, equal parts nihilist and narcissist, Yiannopoulos is the model Trump advocate. And as Trump comes under increasing scrutiny, Yiannopoulos, who writes for, has gone to great lengths defending the worst elements of his campaign. Shortly after our encounter, which took place this March over brunch in Washington, Yiannopoulos published a long article championing the “alt right,” the largely Internet-based, populist movement that has surged to prominence on the heels of Trump’s success. Among its various constituencies, the alt right is comprised of mens’ rights advocates, pseudo-intellectual “race realists,” technocratic authoritarians whose paeans to Chinese efficiency resemble those of Tom Friedman (if Tom Friedman thought Ian Smith was a sell-out), and outright neo-Nazis. Speaking of the movement’s “intellectuals,” the bulk of whom write for avowedly racist and anti-Semitic publications like VDARE and American Renaissance, Yiannopoulos and his co-author described them as “dangerously bright.”

Yiannopoulos has also popularized the movement’s favored insult, hurled at mainstream conservatives deemed insufficiently willing to fight the pernicious wrath of the left: “cuckservative.” A portmanteau of cuckold and conservative, this sobriquet is meant to ridicule the spinelessness of conservatives who fail to acknowledge the greatness of Donald J. Trump. Drawing on a visceral sense that the establishment right actually takes pleasure in being humiliated by its intellectual adversaries, the roots of “cuckservative” are simultaneously pornographic and racist, intended to conjure images of flaccid white men watching their wives be sexually penetrated by blacks. The anti-Semitism of Trump’s alt right supporters, meanwhile, has been well-documented by Armin Rosen here at Tablet, myself in Commentary, and Jonathan Weisman of the New York Times, who faced a barrage of Jew-hatred on Twitter after merely posting an article critical of Trump. So worrying is the issue of Internet harassment of journalists that the Anti-Defamation League recently launched a task-force, including Leon Wieseltier and Tablet contributor Todd Gitlin, to address it.

Asked recently by Internet TV host Dave Rubin about this very phenomenon, Yiannopoulos nonchalantly replied:

Generation Trump, the alt right people, the people who like me, they’re not anti-Semites. They don’t care about Jews. I mean, they may have some assumptions about things, how the Jews run everything; well, we do. How the Jews run the banks; well, we do. How the Jews run the media; well, we do. They’re right about all that stuff. … It’s a fact, this is not in debate. It’s a statistical fact … Jews are vastly disproportionately represented in all of these professions. It’s just a fact. It’s not anti-Semitic to point out statistics.

What was actually most notable about Yiannopoulos’ loathsome reply was his avowal of Jewish identity, something he only mentions when the undeniable anti-Semitism of his followers becomes an issue. Though he has recently taken to claiming, when it suits him, matrilineal Jewish heritage, Yiannopoulos identifies religiously as Catholic, and he used to write a column for a Catholic newspaper in Britain. Nor did his alleged Jewishness stop him from sporting an Iron Cross medallion around his neck as a younger man.

Yiannopoulos pulls a similar trick when it comes to race. He himself cannot be a racist, nor can any movement with which he’s involved be accused of racism, because, as he put it to the New York Times, he has a “very anti-white bedroom policy.” Usually Yiannopoulos expresses his sexual predilections in more prurient fashion, with repeated mention of his desire for “black dick.” Yiannopoulos’ act is designed for a young, male, heterosexual audience that gets a rise out of such outlandishness, in other words, a huge segment of Trump’s constituency. It quickly becomes tiresome, however, to adults of whatever sexual bent.

Never mind how fetishizing African American men as sex objects complicates one’s contention that he is devoid of racism. Like the insistence that he can’t be an anti-Semite because his mother has Jewish ancestors, Yiannopoulos’ assertion that his carnal desires inoculate him from the charge of bigotry is a deflection ploy. Ironically, it’s also a form of the identity politics he claims to despise. While the “social justice warriors” (SJWs) Yiannopoulos mocks say they cannot be racist or anti-Semitic on account of their identities, Yiannopoulos flimsily asserts the same about himself. The alt right should be absolved of similar imputations, Yiannopoulos says, because its spokesman is a gay half-Jew with jungle fever.


With his homosexual minstrelsy in service of America’s first nakedly authoritarian presidential candidate and the extreme right-wing political movement that backs him, Yiannopoulos inspires comparison to “Diamond and Silk,” a pair of black women YouTube stars and fellow Trump supporters who speak in an exaggeratedly African American street vernacular to express support for a presidential candidate who pointedly refused to disavow the endorsement of the Ku Klux Klan and David Duke two days before the Louisiana Republican primary. All essentially perform stereotypical characters (the bitchy queen, the loud black woman) before audiences that, needless to say, are probably not well-represented among donors to the NAACP or Human Rights Campaign. (So hungry for fame are these “Stump for Trump” ladies that they even appeared on a white nationalist talk show.) Yiannopoulos’ gay blackface combines the mincing camp of Quentin Crisp with the reactionary politics of Jörg Haider and is the sort of thing that might have been mildly amusing on a pre-AIDS-era episode of Hollywood Squares.

Simultaneously vacuous and sinister, equal parts nihilist and narcissist, Milo Yiannopoulos is the model Trump advocate.

When we met in Washington, Yiannopolous was in the midst of his nationwide “Dangerous Faggot” tour of American college campuses, the typical visit characterized by a short, inflammatory speech by Yiannopolous about political correctness (which may consist of little more than him uttering “Feminism is cancer”), and raucous student protests. No minds are changed and no intellectual debate is had, but both sides get what they came for: Yiannopoulos feeds his ego as the self-declared “most hate-read journalist working today” and the students feel virtuous for challenging a misogynist pig.

Befitting someone vying to be Ann Coulter’s gay male doppelgänger, Yiannopolous’ shtick is shouting outrageous things solely designed to upset liberals. He has nothing original or interesting to share; criticizing American colleges and universities for abandoning the foundations of classical education has been de rigueur on the right since William F. Buckley Jr. published God and Man at Yale six decades ago. What has garnered Yiannopoulos so much attention, rather, is not anything he says but rather the crude and bombastic way in which he says it. If the ideal protégé of the American conservative movement has been modeled on Buckley—earnest and erudite stewards of free markets and the Western tradition standing athwart history yelling “stop”—Yiannopoulos is its attitudinal antithesis, a right-wing Bluto Blutarsky.

From his perch at and on his Twitter feed, Yiannopolous made it big on the heels of “Gamergate,” one of those Byzantine, online scandals the exhaustive intricacies of which are knowable only to those with skin in the game or too much time on their hands. Basically, the controversy erupted after the ex-boyfriend of a female video-game developer wrote a series of blog posts accusing her of having slept with influential members of the industry to advance her career. As this is the Internet, those blog posts inspired a stream of sexist attacks on the young woman, up to and including the public revelation of her address and phone number in addition to numerous death threats. The contretemps ignited a broader and ongoing debate about ethics and the representation of women and racial minorities in video games. According to the angry game players who adopted “Gamergate” as their byword, the gaming industry is plagued by a cabal of censorious SJWs conspiring to take all the fun out of video gaming.

Yiannopolous quickly emerged as one of Gamergate’s most high-profile champions. Skillfully capitalizing upon his visibility as a charismatic antagonist of “SJWs” in the realm of video games, he offered himself up as a brash personality willing to battle progressives of all stripes, whether they be feminists, campus activists, or the gay rights establishment. For a while, there was something admirably mischievous in Yiannopolous’ antics, which combined the unsettling nature of an Andy Kaufman routine tinged with the rebelliously conservative spirit of the late Andrew Breitbart, eponymous founder of the website for which Yiannopoulos writes. But like the musings of the gangly blonde (and increasingly unhinged) firebrand he so admires, Yiannopoulous’ exploits became less funny once they developed real-world political consequences.

Yet upon closer examination, Yiannopoulos appears less an ideologue than a rank opportunist who is using politics to make a buck and become Internet famous. His career back in Britain, which ended rather ignominiously after a website he founded collapsed amidst accusations that he failed to pay employees, is largely unknown to his American devotees. That’s probably to their benefit considering how he once ridiculed video game players as “unemployed saddos living in their parents’ basements” before realizing the potential that championing their cause might have in launching his name across the pond.

Shortly after Yiannopoulos published his defense of the alt right, Buzzfeed reported that Yiannopoulos himself is “a group effort,” his public persona the work of many uncredited helping hands. According to Yiannopoulos’ former associates, his articles, voluminous Tweets, and other social media postings represent the collective work of some 44 interns dispersed around the world who collaborate, at his beck and call, over the Internet. “Milo Yiannopoulos is not one person,” a former intern told Buzzfeed. Initially, Yiannopoulos did not dispute the story, stating, “It’s completely standard for someone with a career like mine to have researchers and assistants and ghostwriters.” After his curtain was pulled open, however, the new media Wizard of Oz tried to imply that he had hoaxed Buzzfeed, the article being an April Fool’s joke perpetrated on a hapless tech reporter by Yiannopoulos himself, though none of the article’s factual claims were ever disproven.

Though his gay dandyism and adherence to the maxim that “there is only one thing worse than being talked about and that is not being talked about” stirs comparisons to Oscar Wilde, Yiannopoulos more resembles another literary archetype, satirized by great American novelists from Mark Twain to Tom Wolfe: the British fraud who, by dint of his accent and charm, manages to fool Americans into thinking he’s far cleverer than he actually is. From the fictional Duke and King, grifter confidence men who trick Huckleberry Finn into believing they are disinherited European royalty, to Peter Fallow, the hard-drinking tabloid reporter in Bonfire of the Vanities, Americans have been wise to this affectation for well over a century. Occasionally, however, we still fall for it.

To be sure, I enjoy critiquing self-righteous campus leftists as much as the next right-of-center journalist. But only as long as there is some overarching purpose. The anti-free-speech ideology increasingly embraced by university administrators and mainstream liberal writers is wrong not just on account of its censoriousness, but because it deliberately stigmatizes a particular set of ideas as immoral and unworthy of discussion. As much as they rightly decry this anti-intellectual climate, conservative intellectuals should ultimately be more eager to debate the actual substance of those proscribed ideas—free market economics, a colorblind legal system, American global hegemony, etc.—than trolling hypersensitive liberals. With Yiannopoulos, however, one suspects that there is nothing there beyond the petty insults, which is why he never advances beyond mockery and into substance. If his escapades were performed in the service of some discernible ideological goal, (advancing the cause of supply-side economics, say), they would be more intellectually defensible, regardless of one’s political disposition. As it is, Yiannopoulos is just a tedious bully, making him the perfect surrogate for the thoroughly postmodern Trump, who similarly believes in nothing other than himself.

Like that of most bullies, Yiannopoulos’ behavior says more about his own character than it does the people he attacks. Yiannopoulos has stated that he would change his sexual orientation if he could, a desire he certainly shares with a large but quiet number of gay men yet which nonetheless indicates a deep sense of personal shame. “I didn’t like me very much and so I created this comedy character,” Yiannopoulos revealed to the website Fusion last year when asked how he became the bombastic media personality he is today. “I don’t have feelings to hurt” he admits to the New York Times. It’s an age-old story: A self-loathing gay man internalizes the bullying and social ostracism to which he’s been subjected and takes it out on others.

Designed solely to titillate its audience, “Milo Yiannopoulos” is a caricature of what resentful, misanthropic, frat bros believe a gay man to be: morally depraved, sexually licentious, and utterly self-aggrandizing. Unlike the old Milo, the new Milo gets to have creepily adoring fans and, in his telling, sex with lots of black dudes. Unlike old Milo, new Milo sells his own brand of T-shirts. And unlike old Milo, the product of a broken home, the new Milo has a “Daddy” in Donald Trump.


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James Kirchick is a Tablet columnist and the author of Secret City: The Hidden History of Gay Washington (Henry Holt, 2022). He tweets @jkirchick.