Perhaps it was the earnestness with which the editor went about his task, writing clipped, direct notes of feedback to the conservative media figure, who made a name for himself by making outrageous statements designed to raise people’s ire.

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“Delete irrelevant and superfluous ethnic joke,” the editor writes in one comment.

“This entire paragraph is just repeating Fake News,” he says later.

“Use another word here,” one comment reads where the editor crossed out the word “Cuck,” a favorite in the lexicon of the new far right.

Yiannopoulos’s book deal, which was disclosed in late 2016, capped an extraordinary period for the conservative media figurehead, a British provocateur who gained a following through his work for the website Breitbart and the seemingly never-ending chain of controversies that followed him.

Despite a history of inflammatory statements, many of which played on fraught notions of race, gender and sexuality, Yiannopoulos was awarded a six-figure advance by the major publishing house, representing perhaps the most prominent attempt to bring the writer and his incendiary routine into the mainstream fold.

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The publishing house defended its decision at the time, saying that the book would be about free speech and asking readers to “withhold judgment until they have had a chance to read the actual contents of the book.”

The proposal was sharply criticized by many on the left, and the deal was canceled by Simon & Schuster after videos surfaced in which Yiannopoulos appeared to endorse pedophilia. The ensuing controversy also cost Yiannopoulos his perch at Breitbart.

Yiannopoulos filed a lawsuit against Simon & Schuster in state court in New York that alleges the publisher wrongfully terminated his contract, causing “irreparable harm” to him and his value as a public figure. And it was through this lawsuit that the manuscript emerged, with chapter names like “Why Feminists Hate Me,” “Why Black Lives Matter Hates Me,” “Why Muslims Hate Me” and so on.

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Ivers did not return multiple requests for comment.

In the manuscript, the editor works hard to remove what he described as the incendiary humor, baseless accusations and questionable facts. A bizarre paragraph that repeats a hoax theory about a satanic sex ring connected to Hillary Clinton is deleted in its entirety.

“This entire paragraph is just repeating Fake News,” the editor writes. “There was NO blood, NO semen and there was NO Satanism. Delete.”

A comparison Yiannopoulos makes equating Hollywood and Nazis is similarly excised. “I don’t like using Nazi analogies,” the editor writes. “Ever. Let other people do that.”

The editing seemed to be an attempt to shape Yiannopoulos into a writer who could be read by a wide audience. A flabby joke about a frat boy’s anatomy prompts the reminder that the book should be written to a broader audience than Yiannopoulos was accustomed to at Breitbart.

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The editor seems incredulous when presented with racist jokes.

“Rephrase this,” the editor writes about Yiannopolous’s sentence about being romantically interested in “denizens of the dark continent.”

“It sounds like ‘darkies.’”

After Yiannopolous defends the white nationalist Richard Spencer as someone “who genuinely wants a ‘peaceful ethnic cleansing’ of the United States,” the editor seems to believe the statement is insincere.

“ ‘Genuinely’ is the wrong word here — makes it sound as if you’re okay with that,” he writes.

Yiannopolous writes about “autists on the Internet”; the editor says that “autists” “sounds like a mental health slur.”

In the context it was used, it was.

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While many found humor in the edits on Thursday, others said that the editor’s work on the manuscript made him complicit in Yiannopoulos’s views.

“The publisher knew who Yiannopoulos was when they gave him a $255,000 advance,” the writer Jamil Smith wrote on Twitter. “The editor’s brutal comments are somewhat entertaining, but none of this should distract from the fact that they sought to make his bigotry both digestible and marketable.”

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A satirical tweet by comedy writer Ziwe Fumudoh imagined the editor asking Milo if there was “a more palatable word for ‘genocide.’ ”

In an affidavit submitted for the lawsuit, Ivers said that he played a large role in acquiring the manuscript but was “disappointed with the work.”

“It was not the serious and substantial commentary on free speech and political correctness that we expected and discussed,” he said. “Instead, it was a superficial reworking of Mr. Yiannopoulos various speeches where he fed one-liners to crowds and made incendiary comments. Most troubling, it was riddled with highly offensive commentary and ‘jokes’ that were distractions and many would see as racist, misogynist, anti-immigrant, anti-Semitic, or homophobic.”

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Yiannopoulos countered on his Facebook page, sharing texts purportedly from the editor.

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“Don’t quote me but you done good,” one read. Another shared a prediction the book would sell well and accolades from one of the publisher’s publicists.

“She’s a big supporter,” the text read.

The entire episode comes as a fringe group of conservatives espousing extreme views have become increasingly vocal since the election of President Trump.

It has been mostly downhill for Yiannopolous, though. A self-fashioned “free speech” warrior, he has taken aim at speeches given by those on the left.

And most damaging, perhaps, were allegations, first published in BuzzFeed, that he sought the input of a neo-Nazi and a white nationalist as he worked on a piece about the so-called “alt-right.” BuzzFeed also published a video that showed him leading a rendition of “America the Beautiful” at a Dallas bar as his audience did Nazi salutes.