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Once he built a tower made of repurposed 4chan garbage, shit and drivel and bile. Once he built a tower, now it's done. Brother, can you spare a dime ... for Milo Yiannopoulos?
Just kidding. Hold onto your dimes. He doesn't deserve them. He is, however, broke as shit and $2 million in debt, owing money to several fellow internet bigots, Cartier, a wedding venue and a variety of other sources, per The Guardian :
The documents indicate that as of April 2018, Yiannopoulos owed $1.6m to his own company, $400,000 to the Mercers, $153,215 to his former lawyers, $76,574 to former collaborator and Breitbart writer Allum Bokhari, and $20,000 to the luxury jewellery brand Cartier.
As of 2 October, Yiannopoulos owed sums of several thousand dollars to far right writers including Ian Miles Cheong, anti-Islamic ideologue Pamela Geller and science fiction writer Theodore Beale, aka Vox Day, the documents indicate, amongst others.
The documents obtained by The Guardian were published on the website of another far-right wacko, Neil Erikson, who was somehow involved with the drama between Yiannopoulos and the promoters of his planned tour to Australia alongside Ann Coulter. The tour was canceled in October of this year, and refunds were not given. Rather, ticketholders were given tickets to go see the equally repulsive duo of Tommy Robinson and Gavin McInnes. Of course, that too has since fallen through, as McInnes was recently denied entry to Australia after having being judged to have "bad character" (NOT WRONG), so probably now they will just get tickets to see someone's weird racist uncle in conversation with a guy who screams about socialism outside of a subway entrance. Same diff!
The cache of documents also reveals emails from Milo begging the Australia-based promoters, Ben and Dan Spiller, for more money to cover his extensive and entirely unrelated bills.
The documents show Yiannopoulos demanding money from the promoters for his living expenses, medical bills for himself and his husband, and payment for his employees, on top of sums that the promoters claim they had already transferred to him.
At one point, as he attempts to negotiate the transfer of more funds from the Spillers, Yiannopoulos remarks in a message that "I am less financially secure, more panicked and stressed, and more miserable than when we started", and then says he returned his wedding ring to Cartier to wipe out the debt he had with them.
So much for "personal responsibility," huh!
Ever since he got kicked off of Breitbart, lost his Simon & Schuster book deal, got dumped by the Mercers, and was booted off of Twitter, Yiannopoulis has more or less disappeared -- which just goes to show you that deplatforming works. This also has meant that he's had a real hard time making money off of being a giant asshole, especially when there is so much competition these days among other relatively interchangeable wingnuts who also want to be rich and famous for being giant assholes.
It seems this has been going on for a while, as back in August, Poor Milo posted (and subsequently deleted) a rant to Facebook yelling at his fans for not giving him enough money or taking to the streets whenever he is wronged EVEN THOUGH he was basically the whole reason for Donald Trump being elected.

TL;DR: WAAAAAAAHHHHHHHHH!
Milo is, however, still hoping to go to Australia, as he's joined the Deplorables tour (the one with Robinson and McInnes, who still can't get into Australia) sponsored by Penthouse Australia publisher Damien Costas. He announced this in a ridiculous two-hour YouTube rant (my god, who the hell listens to these things??) in which he also yelled at the Spillers for supposedly screwing him over. Subsequently, the Spillers were harassed by the 10 or so people who still pay any attention to him:
The Spillers told the Guardian that they had since received threats from unknown people via text and email. They said a group of men broke into a car at their home on Saturday morning, which they reported to police. The Guardian has seen video that the Spillers say shows them chasing these men down the street away from their home.
This is not the first time Yiannopoulis has found himself in a pile of debt. In 2013, he had to shutter his site The Kernel (which was then bought by The Daily Dot) after it went bankrupt, and then never paid any of its contributors the money they were owed. Call me crazy, but it seems like it might not be a good idea to work for or with Milo Yiannopoulos if you are at all interested in getting paid. It also seems like it might not be a good idea to make an entire career out of being an asshole -- because if you're such an asshole that you get kicked off of the social media platforms you need to get the attention required for such a vocation, you're gonna be shit out of luck.
Of course, despite constantly complaining about how he is broke and the world owes him way more money, Milo firmly denied his brokeness to The Guardian when asked, claiming to be pulling in $40,000 a month.

[ The Guardian ]
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Milo Yiannopoulos Is Broke As Sh*t
Dude makes all of us homos look bad, and it’s not just his politics.
I don't think many of us see him as the poster boy for homos.
He makes human beings look bad.