The life of Milo
Griftwatch , Issue 1683

“IF I had any clue that anything remotely like this was even possible, I would never have got involved in supporting Trump in the first place and I’m very ashamed that I did,” announced an apparently contrite Milo Yiannopoulos recently after the previously rabid MAGA-ist fell foul of his own hero’s policies and was forcibly removed from the US.

So how long will this particular reverse ferret last, given that his career for nearly two decades has consisted of sucking up to rich patrons and gullible fans who will bankroll him until they realise he is as appalling as he pretends to be?

2009
Milo Yiannopoulos (né Hanrahan, sometimes going by Wagner) gains prominence as a Telegraph blogger under the reign of comment editor Damian Thompson, now associate editor at the Spectator.

“We had an astonishing pool of talent – Norman Tebbit, Toby Young, Stephen Hough, James Delingpole, Cristina Odone, Ed West, Jenny McCartney, Nicky Haslam etc etc,” mused Thompson recently, cruelly forgetting to include his former close protégé in his all-star roster. “Then the Telegraph scrapped them and took them all down.”

2011
After losing the Telegraph thousands of pounds on a chaotic awards ceremony he organised for tech start-ups, Yiannopoulos departs the paper. He launches his own site, the Kernel.

2013
Uh oh! The Kernel implodes. Yiannopoulos is sued by two former employees for unpaid wages. He describes the female one as “a common prostitute” for wanting to be paid. The employees win.

2015
Yiannopoulos becomes a tech columnist at Breitbart, an “alt-right” website run by MAGA mogul Steve Bannon and backed by the billionaire Mercer family. He publishes stories such as: “Milo On Why Britain Should Leave The EU – To Stop Muslim Immigration” and a pro-Trump paean titled “It’s Time To Get Behind Daddy”.

He is generally treated as a charismatic, roguish provocateur. Leaked emails reveal Bannon’s own view of his journalistic capabilities: “Your [sic] full of shit. The tech site is a total clusterfuck – meaningless stories written by juveniles.”

2016
Milo is videoed performing “America the Beautiful” in front of a crowd performing Nazi salutes. He claims “severe myopia” prevented him noticing, and says: “As someone of Jewish ancestry, I of course condemn racism.”

The next year, a leaked trove of his emails reveals that one of his passwords is “LongKnives1290”, a reference to the infamous Nazi purge and the year Jewish people were expelled from England.

That July, he is banned from Twitter for leading a harassment campaign against the black Ghostbusters actor Leslie Jones which led to her receiving thousands of racist messages. He declares this demonstrates Twitter is “a no-go zone for conservatives”.

February 2017
Ahead of a high-profile appearance at CPAC, the forum for American conservatism, a clip of Milo resurfaces in which he says 13-year-old boys can have relationships with adult men “perfectly consensually”.

He insists he doesn’t condone paedophilia and claims to be a survivor of child abuse himself, but he loses his job at Breitbart nonetheless. Soon after, he persuades the Mercers to help fund his new venture, the modestly titled Milo Inc, but they withdraw months later, declaring they “were mistaken to have supported him”.

July 2017
Yiannopoulos files a $10m suit against Simon & Schuster for cancelling his memoir Dangerous, for which he had received an $80,000 advance.

The lawsuit reveals his editor’s comments, which include: “The way you casually bring up the KKK makes no sense,” and “The use of a phrase like ‘two faced backstabbing bitches’ diminishes your overall point.”

2018
Milo Inc collapses. Milo tries to pay off his huge debts with a speaking tour of Australia, but he falls out with the promoter and the tour is cancelled.

2021
Milo announces he is now an “ex-gay” and has embraced Catholicism. (This is bad news for his husband, who is “demoted” to his roommate.) He appears on a Christian shopping channel selling statues of the Virgin Mary.

2022
He goes to work for Kanye West, just as the rapper switches from eccentric Kardashian husband to off-meds bipolar Hitler enthusiast. He brokers a dinner for Ye and the white supremacist virgin Nick Fuentes with Donald Trump at Mar-a-Lago. His Twitter account is reinstated by the platform’s new owner, Elon Musk.

2024
With Trump heading back to the White House, Milo founds a talent company, Tarantula, to represent other formerly cancelled people. Within weeks, he loses his most high-profile client, rapper Azealia Banks, who posts that “this company name is my intellectual property you unoriginal piece of dick cheese”, adding: “LMAO now shut up before i call ICE.”

Milo also posts a long screed on Twitter about fellow Trump fanatic Laura Loomer, describing her as “Moronica Lewinsky”.

2025
Milo’s husband-turned-housemate files for divorce, imperilling his immigration status. Undeterred, Milo enthusiastically tweets about immigration enforcement.

“What is the etiquette if you are going about your business and find yourself observing an ICE raid?” he asks his X followers. “I want to show a little respect and decency. Are you allowed to masturbate where you stand, or should you find some kind of awning or motor vehicle?”

August 2026
Milo is detained by ICE for overstaying his visa. (No word on whether an awning was provided.) Laura Loomer takes credit for dobbing him in.

With typical pettiness, the Trump administration makes sure to post Yiannopoulos’s unflattering mugshot. Milo lands in the UK and heads straight for an inevitable interview with that other ever-adaptable and unflushable media fixture, Piers Moron. And on we go!

More top stories in the latest issue:

POLL DANCERS
The Telegraph and Times didn’t exactly trumpet their own roles in pushing the polls commissioned from JL Partners on behalf of Reform UK.

SIC TRANSIT GLORIA
The Times had to hastily rewrite its obituary of trailblazing American feminist Gloria Steinem, who had died aged 92, because it was, er, sexist.

AXEL GREASE
New accounts show German publishing group Axel Springer lent the Telegraph £7m to help with the costs associated with its long-running takeover.

MIDNITE TOIL
The Sun has renewed its partnership with start-up betting firm Midnite, which has had an impressive number of ad campaigns banned by the ASA.

OFF HER BLOCK?
“We believe in a free press,” Kemi Badenoch boasted last week. That was news to those journalists who were banned from her own party conference last year.

NORTH BY NAME...
The sound of reversing ferrets continues to ring out across Reach plc, with the bang-on-Burnham-trend opening of “Mirror North”.

PINK SLIP
The Financial Times ran a long feature on detection of AI in text last month – but it glossed over how it had spectacularly filed in that regard itself.