When Simon & Schuster paid alt-right figurehead Milo Yiannopoulos a $250,000 advance for the rights to his book 'Dangerous' they were pretty certain it would be a big seller.

The book's release was shelved by the publisher earlier this year following an outcry over Yiannopoulos's controversial comments about sexual relationships between men and young boys.

Yiannopoulos subsequently filed a lawsuit against the company and claimed that their decision to drop the book was "opportunistic" and a politically motivated act.

Newly released court documents have revealed a Simon & Schuster executive's concern over the manuscript's content and scathing remarks made to Yiannopoulos about his writing.

In an email to Yiannopoulos and his agent in January 2017, senior editor Mitchell Ivers made it clear that the book would not be published in its current form.

He wrote that one chapter "needed a better central thesis than the notion that gay people should go back in the closet" while another chapter about feminism was also blasted for claiming feminists were "ugly, sexless and own cats."

Detailed comments made in the annotated book manuscript were even more severe. Ivers said one section of the book was "phenomenally petty" while another "didn't pass intellectual muster". It was requested that one passage be deleted for being "unclear and unfunny."

Simon & Schuster also demanded that Milo write a section about actor Leslie Jones which had been omitted from the original draft. In 2016, Milo's Twitter account was permanently suspended by the social network after it was deemed that he incited a racially-motivated campaign against the black actress for her role in the all-female Ghostbusters reboot.

According to the ongoing lawsuit, the book was "plainly not acceptable to Simon & Schuster for publication".

Dangerous was eventually self-published and became a bestseller on Amazon when it was released in July 2017. According to some reports, a ghostwriter was used by Yiannopoulos during the writing of the novel.

The book explores themes such as freedom of speech in the press and Milo's own provocative persona which has seen the British-born personality grow into one of the most divisive figures in American politics.

Far-right speaker Milo Yiannopoulos appears at University of California, Berkeley, even though a weeklong conservative free speech showcase was scrapped (24 September)
Far-right speaker Milo Yiannopoulos appears at University of California, Berkeley, after a week-long conservative free speech showcase was scrapped (24 September) Reuters