‘Yiannopoulos’s career since 2017 has been a shadow of its former glory.’ (Chip Somodevilla/Getty)
In 2017, addressing the fallout from remarks in which he appeared to condone paedophilic relationships between older men and boys, Milo Yiannopoulos held a press conference in New York. Making a ham-fisted attempt to turn the outrage back on his critics, the alt-Right’s defrocked pantomime dame said of sexual abuse: ‘It’s not the worst thing that’s ever going to happen to you. Going bankrupt is worse.’ One wonders where this no-holds-barred provocateur, who in his pomp was both the engine and the product of the caustic, hyper-online alt-Right, would place ‘being deported’ on his curious sliding scale of personal tragedy. For that is how Yiannopoulos’s time in America has come to its sordid end, after ICE agents arrested him at an airport in New Orleans on Thursday.
It transpired that the former Breitbart News journalist, 41, had missed an immigration appointment in July; according to a rather gloating tweet by the Department of Homeland Security, he had entered the US legally in 2019 but had outstayed the terms of his visa. A dishevelled-looking Yiannopoulos, to whom time has perhaps not been kind, mean-mugged the camera in an accompanying photograph. With barely disguised smugness, the department wrote: ‘We encourage all illegal aliens to take control of their departure with the CBP [Customs and Border Protection] Home App.’ Yiannopoulos may have seen himself as above the category of illegal immigrants he’d spent his career despising; in the end, he was treated just as indecorously as the rest of them. To pour further salt in the wound, the post encouraged other would-be immigrants to seek ‘the right legal way to live the American dream’; for Yiannopoulos, it appeared, that dream was very much over.
How had this happened? The British agitator’s rise and fall from 2014 was the life-cycle of the alt-Right distilled in one man: he went from shouty grub to poisonous rockstar to a husk tangled in the web of the movement which by now had become the establishment. He had made many enemies on his rise from Telegraph journalist to alt-Right superstar, racking up public feuds with, among many, Ben Shapiro (a ‘less professionally successful version of me’), the comedian Leslie Jones (he called her ‘spectacularly unappealing’ in a rant that saw him booted off Twitter in 2016), and fellow internet outlaw Azealia Banks, who he had once represented at his refuge-of-the-cancelled talent agency Tarantula Management before a spectacular spat which culminated in Banks presciently threatening: ‘LMAO now shut up before i call ICE on you and get you deported you filthy migrant’. Yet none of these former sparring partners ultimately did him in. No, the final clobber was delivered by Yiannopoulos’s fellow conservative media darling and former pal Laura Loomer, who claimed his scalp by telling X that she’d snitched about his immigration status to the authorities.
The pair fell out when Yiannopoulos accused her of having sexually harassed a young male aide during her congressional campaign in 2020 (which Loomer denies). Baby Jane-worthy barbs culminated in Loomer claiming he ‘was a demonic force’ who had called for her assassination and threatened to ‘throw my bulldog off the balcony’. Now that pooch can sleep soundly in the knowledge that its loving pawrent, whom Yiannopoulos also smeared as Trump’s alleged mistress, shopped this very naughty boy to ‘Daddy’ (as Yiannopoulos called the President). In a final blow that was not a grain of pettiness short of a nanny-nanny-boo-boo, Loomer wrote of the increasingly anti-Israel Yiannopoulos: ‘Milo is going to be deported back to the UK where he can live among the Muslims he has recently chosen to embrace.’ Revenge, served ICE-cold.
The problem with being the Mean Girl of social media — Yiannopoulos has spent years shooting poison darts from the perch of his feared and revered @nero X account — is that the ancient texts have a habit of coming back to haunt you. On Friday the poster AG Hamilton unearthed a gem from the archives: a tweet from last year in which Yiannopoulos joked about the ‘etiquette’ of masturbating at the sight of an ICE raid. It was one of the many approving things he’d said about the agency since it began its crackdown at the start of Trump’s second term; in the end, he looked a wanker indeed.
It’s tempting to see the saga of Yiannopoulos as that of a juggernaut who ran out of road, an open-and-shut case of poetic justice meted against a hateful gobshite. But in truth his rise and fall is more interesting than that: his flamboyant career ultimately indicates the broader health of the alt-Right. In 2016 Breitbart’s star writer, bylined only as ‘Milo’, embarked on his ‘Dangerous Faggot’ tour of US college campuses — the ragebaiting debate format which would later be imitated by the Turning Point speaker Charlie Kirk. His boss Steve Bannon had just defected to run the Trump campaign; the tour was a victory lap for the mainstreaming of ironic hard-Right populism, whose many viral moments thrilled crowds like Nero’s Roman candles.
At Rutgers University in New Jersey, student libs smeared fake blood on their faces and chanted ‘Black lives matter!’; right on cue, the Milo fans responded: ‘Trump, Trump, Trump!’ At DePaul in Chicago, no-platformers stormed the stage and grabbed the mic; hundreds of supporters then marched on the university president’s office. This gave him plenty of set-ups for stylish jabs — when one black student said she’d been ‘silenced for 200 years’, he quipped that she looked remarkably young. At UC Irvine in California, he arrived on stage in a ‘stunning burqa thot outfit’; protesters were handed dummies. The Breitbart write-up included a ‘get the look’ postscript: ‘Combat boots by Diesel, $175. Sunglasses by Gucci, $225. Fishnet stockings: model’s own.’
These stunts were bellwethers for the pyrrhic culture wars of Woke 1, in which expressing heterodox opinions bore the same moral penalty as mass murder. Punchlines could be seeded by simply being outrageous enough. You could set your watch to audiences’ objections — the mantras they’d repeat, the pompous debate-society tactics they’d employ. This was something Kirk would come to leverage in his own campus debates, with liberal opponents never seeming to grasp that by engaging with him at all (or trying to no-platform him) they’d already stepped on the booby-trap. This is also the ‘gotcha’ choreography of today’s X, where the nastiest comeback wins; for all this week’s sniping from poasters delighted at Yiannopoulos’s downfall, it bears remembering that this was a format which he created. In many ways his enemies on the Left and Right were doomed to speak in his language.
But the Regina George of the alt-Right was always going to be burned in the end. The heyday of the Dangerous Faggot tour — in many ways Yiannopoulos’s apogee — was followed only a year later by those paedophilia comments which would see him booted from the line-up at CPAC and dropped from his $250,000 book deal with Simon & Schuster. He also resigned from Breitbart. His career since 2017 has been a shadow of its former glory, as Trumpism’s one-time favourite court jester settled into life as a fringe internet figure, converted to Catholicism, renounced his homosexuality and worked on Kanye West’s turkey of a presidential campaign (it has been suggested that Yiannopoulos was en route to Ye’s New Orleans concert when he was arrested). Being in the wilderness was rough; in 2019 he complained that ‘microscopic [Telegram] followings like 20k are not going to sustain people like me’ and that ‘I can’t put food on the table’, describing himself as a ‘social media refugee’.
Having toured the country as a ‘faggot’, his new life as a ‘100% sodomy-free… ex-gay’ was a particularly inglorious chapter. He reported that he had come to regret ‘mainstreaming homosexuality in the Republican Party’, and was seemingly doing penance by hawking statues of the Virgin Mary on a Christian teleshopping channel — and by announcing plans to open a conversion-therapy clinic in Florida. Yet he has never quite managed to convince in his new ultra-trad packaging. In a manner which must infuriate him, his arrest was digested by X as a scrumptious chapter in a classically gay internet saga, with snark from George Santos (‘I’m the new Alfa [sic] Gay conservative in town’) and others (‘Grindr profile vs IRL’ read one caption comparing images of Yiannopoulos in his bleach-blond prime and in last week’s dour mugshot).
As things stand he’s back in Britain and back on X — and being relatively good-humoured about his deportation. But his reputation as a rebellious princeling will be difficult to salvage now that he has, in the words of Musk, ‘become meme’ by being hoisted by his own pro-ICE petard. It seems unlikely that he will fade away entirely. X is behaving like a classroom of children whose naughtiest constituent has been sent outside: they simply cannot wait to see what happens when he comes back. And with Reform and Restore looking to sweep the next election, now is perhaps a favourable time for the prodigal son to return. Yiannopoulos has carved out a distinctly Yank brand — noisy rabble-rousing may prove terribly impolite in the stuffy halls of Westminster — but this may help him at a time when British politics seems to be mutating into something more brash and populist. What happens in America has ripples in Britain, and Tommy Robinson’s recent ascent — the far-Right activist has spoken at the Oxford Union and gained elite international backing from figures including Elon Musk — suggests greater appetite than ever for the previously unsavoury fringe.
What is certain is that this embarrassing chapter will not convince Yiannopoulos himself of his own inadequacy. It is said that when Nero hesitated to knife himself to death, he cried: ‘What an artist dies in me!’, so convinced was he still of his extraordinary talent. Two millennia later, his X namesake and comparable braggart is surviving the latest of several political suicides, brought low by a system for which he was the greatest cheerleader. Any other flower would wilt in the heat of such crushing irony; this weed looks sure to find a way.
