My World of Flops DELETE UGH Case File #109/My Year of Flops II #6: Milo Yiannopoulos' Dangerous


Milo Yiannopoulos’ doomed manifesto Dangerous was self-published less than two years ago, on July 4th, 2017 after Threshold Editions, Simon & Schuster’s Conservative imprint, joined the rest of the world in getting out of the formerly lucrative Milo Yiannopoulos business once audio was released of the right-wing provocateur seeming to endorse pedophilia as a healthy rite of passage. 

Milo’s career-killing words on the subject are “In the homosexual world particularly, some of those relationships between younger boys and older men are coming of age relationships in which those older men have helped those young boys to discover who they are and give them security and safety and provide them with love and a reliable — and sort of a rock where they can’t speak to their parents.”

Milo learned the hard way that you can say incendiary and provocative things and be elevated to superstardom for your outrageousness. But when you start asking what’s so unhealthy, really, about adults having sex with thirteen year olds, allies and institutions are going to start abandoning you in droves. 

On Facebook, Milo claimed “my usual blend of British sarcasm, provocation and gallows humor might have come across as flippancy, a lack of care for other victims or, worse, ‘advocacy.’ I deeply regret that” but what stands out about that quote after reading Dangerous is how uncharacteristically earnest the words that killed Milo’s career are. Dangerous is sarcastic, provocative, full of gallows humor and flippant about everything. It feels and reads nothing like the words and ideas that sent the Milo movement hurtling straight into a brick wall.

Oh Milo, you rascal! Such fashion! Such panache!

Oh Milo, you rascal! Such fashion! Such panache!

Dangerous was published well into Donald Trump’s presidency. Yet it still has the fascinatingly obsolete feel of ancient history. For starters, the book is an endless victory lap from a dude whose winning streak was about to snap dramatically, with the whole world watching and cheering along. 

In Dangerous’ epilogue, Milo boasts, “I dare to be dangerous every day, and, well, I can’t stop winning.” Milo is like Trump in that his concept of winning looks an awful lot like an endless series of humiliations and defeats from the outside. 

Those humiliations and defeats include Simon & Schuster doing the decent thing and parting ways with Milo after his comments about pedophilia came out. An indignant Milo sued Simon & Schuster. Then, in an unexpected gift from the universe, the complete text of Yianapollis’ Dangerous was made public due to legal wrangling. A schadenfreude-happy public delighting in Yianoppolis’ downfall were able to experience the right wing provocateur’s manifesto as it was meant to be read: through the disapproving and frustrated lens of an editor cursed by the Gods with having to transform Yianopollis’ ugly parade of cheap racism, sexism, Islamophobia, fat jokes, lesbian jokes, Kardashian jokes, Ben Shapiro jokes and self-loathing into a book he and his employers wouldn’t be humiliated to be associated with. 

I was able to make my way through 267 pages of toxic literary garbage, the worst book I’ve read since The Art of the Deal, by imagining the defeated, exhausted and indignant expressions of an editor I’ve decided looks and acts just like J.K Simmons in Whiplash as he trudges his way joylessly through the text, clearly wondering at every step what awful crime he committed in a past life to be punished this way. Needless to say, nothing Milo does as an author or as a literary funnyman, a dreadful shock comic of the written word, is even remotely his tempo. 

Also the name of my favorite Guided By Voices b-side.

Also the name of my favorite Guided By Voices b-side.

The conflict here is not political. The editor is a Republican who works extensively on Conservative books from big-name professional right-wingers for a right-wing imprint. I imagine that Milo and the editor agree in broad strokes, on the big things. 

 Instead the difference is generational and attitudinal, between an online culture of shock and brazen provocation, where it’s enough to simply make an impact and bait the right people, and a literary culture where arguments must be supported with facts and solid reasoning and not jokes about feminists all being homely, ice cream-addicted crazy cat ladies or fantasizing about being gang-raped by college students. 

When Milo references Leslie Jones or the female Ghostbusters reboot, it’s with the arrogance of someone who knows he just needs to drop the right buzzwords or say the right names to get his audience to lose their shit. Milo seems to think that he doesn’t need to explain how his harassment of Jones got him kicked off Twitter, or the basics of GamerGate to readers because they are both such historic triumphs that minstrels sing songs and poets write rapturous odes to the epic victory that ensued when the Great Milo slew the silly movie about the girl ghost chasers, saving humanity and men as a gender in the process.

The endlessly, surreally frustrated editor continually tries to tame his wayward author by arguing that sexist, racist, homophobic, uniformly unfunny jokes and personal insults detract from his argument and his authority. But the truth is Milo the author has no authority and the sexist, racist, homophobic, uniformly unfunny jokes are his argument. Oh sure, Milo lays out plenty of conservative talking points about the evil posed by what he charmingly refers to as Muslim “rape-fugees” and radical feminists in academia and video games but really he’s just agitating for a return to an era where you could joke about Democratic women all being man-hating lesbians and cab-drivers smelling like curry without facing social consequences. He’s in it for the LOLs and the hate.


A good example of what this poor man was up against can be found in an early digression, where Milo confidently asserts, “Speaking of witchcraft, the Clintons have turned into such villains that the demons summoned through their “spirit cooking” sessions take notes on them. It’s like a masterclass in demonic behavior. The demons wonder how she has done it all in one human lifetime. If you want a great example of media bias, imagine if the Trump campaign had been participating in satanic trials involving blood and semen. The closest thing Donald Trump has to occult ritual is his infamous habit of eating KFC with a knife and fork. But even that I think is one of Daddy’s elaborate trolls. 

You have to feel for poor Bill. Every time he hears “gender” and “gap” in the same sentence he gets hard, then he sees Hillary’s crossed eyes and evil smile and he’s booking another flight on the Lolita Express.” 

How do you respond to nonsense of that magnitude? If you’re the editor, you break out the ALL CAPS for emphasis and insist, “This entire paragraph is just repeating fake news. There was NO blood, NO semen and there was NO Satanism. Delete.” 

“Still, I suppose the lesbians need somewhere to go. Look at any gender studies faculty in America and you’re likely to find a list that goes something like, dyke, dyke, dyke, divorcee, dyke, “genderqueer”, dyke, dyke. Lesbians should be thrown out of academia altogether and put back where they belong—porn! God hates fags, but he hates feminists more”, meanwhile, merits a rightfully aghast “DELETE UGH.”

DELETE UGH really applies to the whole book, but the poor editor had to pick his battles.


Milo fills the book with charming sentiments like “I am a gay anomaly—like a lesbian without a violent girlfriend” that cause the editor to complain, “Leave the lesbians out of it!” 

When the editor pleads, “This is not the time or place for a black dick joke” that literally could apply to over a dozen passages.

Dangerous makes transgression toothless, provocation lame, trolling tame. You know how you can tell that Milo isn’t hip? Because he spends so much of the book bragging about how hip he is. Nobody who is genuinely hip needs to broadcast their devastating hipness. 


Milo also spends much of the book joking about how unbelievably sexy and charismatic and desirable he is, much to his editor’s palpable irritation. Given the dad joke level of humor on display here his endless comments about his good looks end up feeling less like the campy theatricality of a queer diva boldly thrusting their sexuality on a public equally titillated and intimidated by it than a corny uncle making endless quips about how sexy new mustache makes him look that we’re expected to chuckle indulgently at even though we’ve heard all of these lame quips before and they were never funny in the first place. 

The same is true of Milo’s endless comments about his predilection for having sex with black men, something he seems to think makes it impossible for him to be racist, just as he can’t imagine how people might think he’s a self-loathing homosexual even though he literally devotes a chapter of his book to arguing that homosexuals should go back into the closet and have children with women for the sake of humanity.  

The editor says of this chapter “This chapter is in the worst shape of any chapter in the book—and it will be one of the most scrutinized. You can’t just toss off poorly thought out theories about going back in the closet, as you might in a college lecture. people will come to this chapter with legitimate questions about how a gay man goes against the gay/liberal grain. You have to meet their curiosity with an appropriate level of intellectual rigor.” 


Intellectual rigor. Ha! The editor keeps trying to drag this back into the classroom, for rebel Professor Milo to teach his adoring and impressionable acolytes inconvenient, unpopular truths. But Milo is intent on keeping the level of discourse at the level of lewd bathroom wall graffiti.

Is Milo joking when he writes, “I hate to exaggerate, but you might say the future of the West sort of depends on us faggots leaping back in the closet and churning out a few kids?” Who the fuck knows? Does he believe that or is he just talking shit to get a response as trolls do? It ultimately does not seem to matter.

The chapter on why gays need to go back into the closet has fierce competition for “roughest shape” with a chapter attacking the fat acceptance movement so dire the editor posits it, correctly, as irredeemable, arguing gravely, “The whole chapter is a problem in tone. Your usual style NEGATES any value your information might have. The presence of the chapter in the book destroys the rest of the book.”

Milo makes so many errors that no one editor can catch all of them. Milo prides himself on being pop culture literate, in sharp contrast to dreary establishment Republicans. Yet he nevertheless asserts of the sinister trend of evil black people trying to make white people feel bad about slavery by occasionally making fact-based film about American history, “There’s a huge trend in movies that seek to channel white guilt over slavery, with movies like Django Unchained, 10 Years a Slave (sic) and MLK. The villains in these movies, always white males, get progressively more sadistic and irredeemable.”

The assertion that the bad guys in those three films are all white should come as a surprise to anybody who remembers Samuel L. Jackson’s rightfully revered performance in Django Unchained as a house slave who is just about the most evil motherfucker alive. Oh, and there is no movie called MLK, you dunce. It’s Selma.


A more eagle-eyed editor would have caught that the film Milo was so apoplectic about is titled 12 Years a Slave although it’s understandable how a film that ancient (four years old) and obscure (it only won Oscars for Best Picture, Adapted Screenplay and Supporting Actress) could be misremembered by someone who spends much of the book scolding the mainstream press for getting facts wrong and being sloppy and biased. 

Dangerous is less a manifesto than the transcription of an endless open mic night stand-up comedy routine. Only instead of playing to his core audience of cultists and fanboys, the kind who will hoot and holler at the mere mention of Leslie Jones, Milo is performing for an audience of one—his editor—who does Milo and the world an incredible service in constantly stopping Milo’s set of the damned to inform him as strongly as possible that the joke that he just told was not funny. Not even a little bit.

To keep himself sane, the editor finds different ways to tell Milo that his sense of humor sucks, his jokes are terrible and that he should be ashamed of himself. After Milo painfully quips of his nemesis Mark Zuckerberg (who he refers to elsewhere as Mark Cuckerberg), “He’s basically like a Jewish girl who moves in bed, it shouldn’t be a big deal but is considering the competition” the understandably annoyed editor grouses, “Gets in the way of the way of the point you’re making and is not even funny.”

The editor’s response to Milo’s assertion that “Women have been nothing more than two faced backstabbing bitches except Mother Theresa…and even she’s suspect” is funnier in itself than Milo’s book is in its entirety. With dry understatement worthy of a young Bob Newhart the editor deadpans, “The use of a phrase like “two faced backstabbing bitches” diminishes your overall point.”

The editor puts his foot down more than once in the name of human decency. When Milo insists, “It turns out that the Hollywood Left is even more racist than the high-level Nazis” the editor nixes Nazi analogies. When Milo refers to trans people as “mentally ill”, the editor fires back “I will not accept a manuscript that label’s an entire class of people ‘mentally ill’.” But when Milo insists that Progressives are only interested in protecting “trannies, Muslims and lonely hambeasts in their thirties” our editor is left to inquire what in the fuck a “hambeast” is. Here’s a hint: it’s sexist and horrible.

Milo predictably thinks a chapter on what he depicts as the poisonous, life and culture-destroying lie of Rape Culture is the perfect place to trot out rape jokes.

Milo can’t even make a statement like“Rape is terrible” without immediately undercutting it with a paragraph quipping, “Well, I assume it’s terrible for most people. Personally, I’ve never gotten off faster than when I’ve had a gun to my temple. My boyfriend will tell you I can’t even get hard these days without a knife to my throat.” 

With deft understatement, the editor informs Milo this is “the wrong joke in the wrong place” and when Milo quips of the gang-rape at the center of the UVA Rolling Stone scandal, “It was something for my sexual fantasies—and perhaps Jackie’s as well. Either way, it never happened” the defeated editor repeats that this is an “inappropriate place for humor.”

He’s like the world’s most useful heckler, a heckler who can keep the rest of the world from being subjected to the very worst jokes.

At times the editor seems rightfully astonished at his would-be collaborator’s ignorance, like when he corrects Milo’s insane assertion that “When America landed on the moon, the Cold War essentially ended” by reminding our hate-filled polemicist “Moon landing was 1969. Berlin Wall didn’t fall tim 1990. Russia winning the space race was NOT the end of the Cold War.”

I hate the messages but I love the fashions! #Conflicted

I hate the messages but I love the fashions! #Conflicted

Milo takes Leftists to task for becoming fun-hating, puritanical scolds who have embraced the mantle of victimhood and become the antithesis of what they stood for in the 1960s. This enrages Milo because he knows that the true victims in 21st century society are straight white Christian men, gamers most of all, fighting an uphill battle against the sinister forces of political correctness and a man-hating matriarchy that won’t be satisfied until we’re all trans Muslim Communists tying homosexuals, widows and children together and then hurling them off mosque rooftops in the name of an Allah who commands us to rape and kill.

Throughout the book, the editor takes Milo to task for embodying everything he rails against, from shameless self-promotion to online harassment. The editor taps into the ridiculous, pearl-clutching hypocrisy at the book’s core when he answers Milo’s indignant assertion, “No one should ever be investigated for hate speech, as Mustafa was, but it’s clear from the example of (feminist writer Jessica) Valenti, who once wrote the headline “Feminists Don’t Hate Men, But It Wouldn’t Matter if We Did”, that hate speech is permissible if it’s done under a byline”—with an indignant and irrefutably correct, “If that headline is hate speech, THIS WHOLE BOOK is hate speech.” 

That’s not a bad description for something with passages like the following: 

*“San Francisco has an online map of human fecal waste. If you bring enough Muslims over, you’ll need a poop map and a rape zone map. Remind me again why that’s a good idea?”

*“When it comes to Islamic immigration, assimilation doesn’t seem to be an option. At least not yet. It’s “When in Rome, rape and kill everyone and then claim welfare.”

“The next time a leftist asks you what you’re doing to fight rape culture, or intolerance, or homophobia, take out a Quaran and burn it in front of his face.” 

Seems a little harsh TBH

Seems a little harsh TBH

Reading Dangerous would be a much different experience without the editor’s notes. They transform an odious monologue from a tiresome fraud hopelessly in love with the sound of his own amateurish literary voice into a hilarious two hander whose plentiful laughs are rooted in the generational and attitudinal divide between Milo and his editor. 

Milo never stops trying to be funny and never succeeds. His editor never tries to be funny and is hilarious from the first page to last. And he didn’t have to rely on cruel humor, or racism, or a potty mouth to make people laugh, albeit unintentionally. Milo could learn from a guy like him, in more ways than one.

I somehow expected more from Dangerous. I assumed that because Milo had catapulted to fame and infamy there must be something to his cult, some spark of wit or insight or gleeful irreverence. 

Nope. This is just fucking sad. It’s not liberating. It’s not fun. 

Milo may present himself as a cross between Ayn Rand, John Belushi in Animal House and a human Spuds Mackenzie out to liberate our campuses, to save them from all the dreary feminists and activists out to spoil their fun and stop their keggers. But there’s nothing liberating or fun about Dangerous. It tries to make Islamophobia, homophobia and racism hip and rebellious, something all the cool kids are doing, the new punk rock. It fails miserably in this and in every other way.

Milo’s appeal seems to be, “Yeah, sex and drugs and partying are fun, but you know what’s really ‘the bomb?"‘ Keeping Muslims out of the country! And Sheriff David Clarke! And that cool cat Rudy Giuliani trying to save the lives of all the soul brothers and sisters, unlike those Black Lives Matter charlatans!”

In Dangerous, Emperor Milo, Trickster God of the Righteous Right Wing Trolls, was inviting an endlessly fascinated public to check him out in all of his outrageous literary finery. Alas, it was evident to everyone that despite the hype and brouhaha about his flamboyant attire, this particular Emperor had no clothes. But one unfortunate, heroic soul cursed with having to transform Milo into an actual author made that realization before anyone else and, through a crazy set of twists, was able to share his book-length horror and revulsion with a morbidly fascinated public more interested in laughing at ol’ Uncle Milo than in laughing with him.


Dangerous isn’t a manifesto, or even a book really, so much as it is a book-length self-own. 

Dangerous as a manuscript: Failure 

Dangerous with Editor’s Notes: Secret Success

I read every last goddamn page of Milo’s book. Does that merit pledging a dollar over at ? I think it does.