There’s a particular kind of vertigo that comes from watching a man build a career on mocking the suffering of others, then ask you to feel sorry for him when suffering finally finds its way to his own door.
Firebrand and far-right troll Milo Yiannopoulos spent the better part of a decade as a professional agent of cruelty — mocking trans people, harassing women out of public life, cheering on the sort of internet mobs that end careers and occasionally end lives — and he did it all with shrill, giggling delight.
Let me start by walking you through what actually happened this week.
Yiannopoulos entered the United States legally in May 2019. After he missed an immigration hearing earlier this year, a judge issued a final order for his removal on July 22, 2026. He did not leave the country.
On Thursday, August 27, ICE agents arrested him at Louis Armstrong New Orleans International Airport while he was traveling through Louisiana.
DHS confirmed the deportation happened the following day, Friday, August 28, with the department publicly announcing it on Saturday, August 29. DHS referred to him as an “illegal alien from the United Kingdom” who had “chose[n] to overstay his welcome in violation of our nation’s laws.”
Two details about how this became public are worth noting.
First, the Trump administration publicized his arrest specifically to promote its voluntary self-deportation program, posting his booking photo on DHS’s X account with a message that detention is a choice and encouraging other undocumented immigrants to use the CBP Home App to self-deport.
Second, right-wing activist Laura Loomer — a Trump ally — claimed credit for reporting Yiannopoulos to ICE, a detail that’s drawn attention given the two have feuded publicly in right-wing media circles before.
After his deportation to the UK, Yiannopoulos gave his first public comments in an interview with Piers Morgan, released September 2, in which he described the experience as making him feel “really, really terrified.”
Give me a fucking break.
Now, back to the point I actually want to make. Yiannopoulos made his name arguing, in various forms, that marginalized people were too sensitive, too demanding, too eager to claim victimhood. Feminists were hysterical ninnies, transgender people were mentally ill, and immigrants are dirty and dangerous.
Last year, Milo blithely asked his followers whether he could masturbate publicly while witnessing an ICE raid.
This isn’t really a story about fucking sadistic asshole, though. It’s a story about a pattern so familiar in modern conservative politics that it barely registers as remarkable anymore: empathy as a one-way valve. Compassion, in this framework, is a currency spent only on people who already look, vote, and worship like they do.
The irony writes itself, but let's sit with it anyway. This is a man who cheered as Trump promised to deport "millions and millions and millions of people," who once posted that "nothing else matters" without mass removal. And now he wants us to sympathize with the “terror” he experienced during his deportation.
Fuck off.
