The rise and fall of Milo, the alt-right poster boy

The latest spat to explode into public is a war of words between Milo Yiannopoulos – a purveyor of hateful nonsense across three continents – and the would-be promoters of his 2018 Australia tour.

After Yiannopoulos published snatches of conversation between himself and his promoters, including unredacted emails and other contact details, they retaliated in turn by publishing swathes of correspondence, including documents appearing to show Yiannopoulos has amassed around $2 million in debts to his own company, suppliers, his writers, and even the venue of his wedding.

The promoters also claimed to have launched legal proceedings to recoup the six-figure sums they had given him in advance of the now-cancelled tour.

Given a reputation which could surely be described by even his most kindly-hearted of admirers as ‘unreliable bordering on erratic’, such debts could easily prove to be well beyond what Yiannopoulos could ever hope to repay.

For most of us, that might mark a moment of horror, a realisation we’d made a series of terrible mistakes, and likely even contemplation about the effect of our actions on those around us – especially those who you’d employed to work for you.

For Yiannopoulos, it almost certainly won’t – because if he does indeed publicly fail thanks to this row and the debts it has revealed, it will not be the first, nor second, nor even third or fourth time he has publicly, disastrously failed.

The reasons are usually financial, often relating to his own bulls**t, and usually leave others with a mess. This might be the biggest in financial scale, but Yiannopoulos’s story is hardly one of a dangerous ideologue.

Instead, it’s that of a serial and erratic attention-seeker, whose inability to hold anything together most reliably harms himself and anyone silly enough to believe in him. Here, then, is a short history of the many failures of Milo Yiannopoulos.

His first professional failure was as a conventional-enough junior staffer at a national newspaper, though even his early career was marked with by a flexible attitude towards reality. Yiannopoulos – born Hanrahan, then presenting as a short time as Milo Andreas Wagner, before settling on Yiannopoulos (and – his old editor’s profile on Wikipedia suggested – an apparent false claim to have been born in Athens, rather than Kent) – was employed by then-Telegraph journalist Damian Thompson to help with a book he was writing, and briefly as an assistant to the liberal activist Bianca Jagger (which ended acrimoniously).

This experience was parlayed into a blogging role for Thompson’s Telegraph comment section, which was soon on rocky footing after Yiannopoulos’s already inflammatory style went beyond what the publication was comfortable with.

His footing in the right-wing publication already shaky, the final straw coming as Yiannopoulos promised to launch a tech awards ceremony for the Telegraph – which descended into chaos, as promised sponsors never materialised (leaving the Telegraph to fund the cost for the event), and a last-minute swap of the winner, without the knowledge of any of the judges who’d picked it.

Bridges resolutely burned, Yiannopoulos swiftly tried again – this time outside the mainstream, and without the hassle of bosses or editors. He launched a small tech start-up, The Kernel, and courted a roster of new writers, even toning down for a short time his usual vitriol.

But even here he had over-promised and under-delivered: in 2012, owing writers thousands of pounds in unpaid wages and fees, The Kernel collapsed acrimoniously. While writers eventually received some compensation, Yiannopoulos’s wrath against those who’d dared to speak out had been substantial.

‘You’ve already made yourself permanently unemployable in London with your hysterical, brainless tweeting, by behaving like a common prostitute and after starting a war with me,’ he wrote to one young female writer, whom he also threatened to ruin by sharing compromising photographs.

By now, Yiannopoulos’s financial messes were already a matter of documented fact for anyone who would look for them: The Kernel was the third UK company launched by Yiannopoulos – the first two never even reported any revenues to authorities before being wound out for failing to file necessary paperwork.

And just as a court had ruled The Kernel owed compensation to its writers, UK courts have ruled against Yiannopoulos – usually in his absence – for personal unpaid bills, on at least seven occasions, for relatively trivial amounts: £403, £75, £225, £660, £1,935, £2,165 and £535, between 2012 and 2016.

In the UK, Yiannopoulos had failed as both a mainstream and alternative journalist, and his television appearances as a controversialist – an anti-gay marriage gay man, for example – were all but drying up. But he was soon to find an escape to a second continent, and a potentially much larger payday.

Whatever appetite for loudmouths the UK has – and it’s sizeable – the USA’s is far larger, far more animated, and seems fond to hear from certain UK people just as Brits get completely tired of the sight of them.

Naturally, Yiannopoulos fitted right into this ecosystem, first tapping into the sub-community of sexist gamers who made up part of the so-called GamerGate movement, which slowly morphed into the so-called ‘alt-right’ and left Yiannopoulos in prime position to become one of its stars.

Discarding a supposedly complete book on GamerGate – another Yiannopoulos project that never quite made it – he threw himself into Breitbart, the far-right website, and becoming a useful pro-Trump voice. Yiannopoulos was never quite let into the real action, but his positioning as a gay, Jewish Trump supporter (Yiannopoulos had previously identified as Catholic, and wasn’t raised in the Jewish faith, though has Jewish heritage) proved useful cover.

This was the nearest Yiannopoulos came to really making it: he was offered a speaking slot at CPAC – one of the Conservative US right’s biggest events – and a $250,000 book deal by Simon & Schuster. And then a video in which Yiannopoulos appeared to at least partially defend or excuse paedophilia emerged, and he was quickly and thoroughly abandoned: he lost his Breitbart job, speaking slot, and book deal in short order.

Further humiliation followed. In a possible bid to save face – or at least recoup some money – Yiannopoulos launched legal proceedings against Simon & Schuster. The proceedings were chaotic, as Yiannopoulos ditched his lawyers (who records suggest he owes around $150,000) and tried to pursue the claim himself, without representation.

However, the suit – which was eventually settled on a ‘walk away’ basis, meaning Yiannopoulos dropped the action – revealed an early draft of his work, complete with scathing edits extensively criticising the book, its arguments, its writing, and more. ‘Unclear, unfunny, delete,’ ended one typical editor’s note.

And so to continent three. Just as the USA has proven willing to give a stage to Brits after the UK has tired of them, Australia has, on occasion, provided a willing platform to them after the USA has had enough.

Trading at the helm of a new and even more self-aggrandising start-up – MILO INC – Yiannopoulos attempted to create a new alt-right media outlet in his own image, and fund it through tours, including a relatively successful 2017 tour of Australia.

Predictably – Yiannopoulos is nothing if not boringly predictable – this quickly followed his usual pattern: spending and boasts vastly outweighed revenue. MILO INC was soon insolvent and the company all but collapsed, leaving Yiannopoulos looking to pay off debts and in need of another tour, which itself all but collapsed.

If the documents recently leaked online are to be believed, the sums involved this time could spell much bigger trouble for Yiannopoulos than before. The documents appear to show him around $1.6 million in debt to his own company – which administrators and tax authorities alike would examine quite closely, if the reports are confirmed.

Other debts include thousands of dollars to writers, venues, lawyers and even around $15,000 to a company offering customised embroidery. As anyone with unpaid legal fees knows, lawyers do not tend to be relaxed about getting their pay cheques.

The astonishing thing about Yiannopoulos’s string of serial failures – which span the globe and some of the world’s biggest stages – is just how repetitive a story it is.

Yiannopoulos is a man with one trick – to gull people into confusing offensiveness with wit, and wit without any form of politics – and numerous flaws, none of which seem to have taught him anything.

Failure is meant to be educational: get something wrong badly enough, and most of us won’t make that mistake again. Yiannopoulos, now in his mid-30s, makes exactly the same mistakes he made in his early 20s, leaving him a man-child, incapable of growing or changing, and unable to take any meaning from the wreckage he has left behind.

That’s a story that might move us to pity – except for the sheer destructiveness and vindictiveness of the performances that got Yiannopoulos the platforms he squandered. Yiannopoulos – whether sincerely believing his crap or not – glorified himself by hurling personal abuse at others, launching racist, homophobic, sexist, and transphobic attacks.

Yiannopoulos is a man beneath pity. He may even be a man beneath contempt. Doubtless, some fool will give him a 10th chance at some point in the next few months. In a decade he’ll be looking for his 27th, or worse, chance.

Yiannopoulos might not be able to learn from his mistakes, but we should learn from ours – he’s never been worth our attention. Can we learn to look away?