When the Hollywood Reporter revealed that alt-right darling Milo Yiannopoulos had scored a $250,000 book deal with Threshold Editions, the conservative imprint of Simon & Schuster, progressives recoiled in horror. How could a respectable publishing house lend its megaphone to Breitbart’s bile-spewing gibberer? Yiannopoulos, after all, had been banned from Twitter after inciting a racist mob to hound Leslie Jones off the internet; he frequently mocks queer and transgender people; and he is known for such bons mots as “There is only one place for lesbians: porn” and “feminism is a bowel cancer.” He’s the kind of lazy troll who battens on outrage, and to treat him as a controversial-but-urgent new voice felt to many like the worst sort of misanthropic opportunism.

In the maelstrom that followed, the Chicago Review of Books announced that it would not review any Simon & Schuster titles in 2017. Calls to boycott the publishing house filled the literary ether. Others objected that a boycott against the larger company was too blunt an instrument to target Threshold, which, like most imprints, operates fairly autonomously under its corporate umbrella. Still others contended that Yiannopoulos’ brand of spite is no more toxic than that of best-selling authors Ann Coulter and Rush Limbaugh. (Though one could argue that they don’t need a platform either.)

The world of conservative publishing is not of one mind about Yiannopoulos. Speaking to the Hollywood Reporter, the 33-year-old provocateur wove a tale of his own effortless star power, as if editors were falling all over themselves to broadcast his words. “I met with top execs at Simon & Schuster earlier in the year and spent half an hour trying to shock them with lewd jokes and outrageous opinions,” he boasted. “I thought they were going to have me escorted from the building—but instead they offered me a wheelbarrow full of money.”

That’s not quite how many of the publishing insiders I spoke to see it. (Simon & Schuster declined to comment for this story.) For one thing, as an editor at a different house explained, $250,000 is not a lot of cash for a celebrity memoir, nor did there seem to be “an auction or anyone fighting over Milo.” Also, “Simon & Schuster” is a deceptively prestigious label for an operation like Threshold, which is not known for radiating literary caliber. Finally, contra his narrative of waltzing out of Threshold with an accidental book deal, it appears that Yiannopoulos was actively shopping his proposal to various right-wing imprints, with minimal success. Multiple publishing houses specifically told me that they had turned down his book.

So—keeping in mind that the logistical details of the deal may be less glamorous, the calculations more complicated, than Yiannopoulos would like us to believe—what actually goes into the decision to acquire a title like Dangerous? What does Threshold stand to gain, and lose?

The conservative book business in the United States has been negotiating its relation to the mainstream since the market’s first stirrings in the ’80s and ’90s. As Constance Grady recently detailed for Vox, the reactionary Regnery Publishing was founded in 1947, but right-leaning imprints didn’t crop up in marquee houses until four decades later, when Erwin Glikes and then Adam Bellow took the reins of the Free Press, a subsidiary of Simon & Schuster. In 1987, Glikes released Allan Bloom’s incendiary tome on political correctness in college, The Closing of the American Mind. Bellow, the son of novelist Saul Bellow and a man for whom, in his words, “howls of outrage from the Zabar’s Left have always been, to me, the sweetest music,” followed that best-seller up with three even more polemical titles: Illiberal Education, by Dinesh D’Souza; The Real Anita Hill, by David Brock; and The Bell Curve, by Charles Murray and Richard Herrnstein. As scandalized readers pulled out their wallets, a similar revolution began to transform the Republican media. Fox News would soon launch a new class of celebrity pundits into the popular consciousness. These pundits—Ann Coulter, Bill O’Reilly, Rush Limbaugh—wanted book deals, too, and during the aughts the “Big Five” publishing houses obliged, unveiling right-wing imprints like Sentinel (under Penguin), Broadside (under HarperCollins), Crown Forum (under Random House, then separate from Penguin), and Threshold (under Simon & Schuster, which had sold the Free Press to Macmillan).* Now, Yiannopoulos represents a new conservative wave, a semi-ironic appeal to racism, sexism, xenophobia, and anti-LGBTQ bigotry that makes explicit what past Republicans preferred to keep concealed. Like Donald Trump, he has bypassed traditional modes of communication to inflame his followers. And so he arguably presents a unique set of questions, both ethical and commercial, for publishers to grapple with.

Sentinel, one of the imprints that ultimately declined to work with Yiannopoulos, explained that its reason for rejecting him was not a moral one. There was concern that Yiannopoulos’ allure as a punk outsider would fail to translate during a Trump administration that mainstreamed his views. “He’s a provocateur,” said Adrian Zackheim, Sentinel’s publisher, “and I don’t mind publishing people who say outrageous things to get people worked up if they can move the cultural conversation in a significant way. But I was looking for evidence of a coherent doctrine.” Other editors similarly felt that Yiannopoulos’ bile did not rise to the level of an ideology. “I think it’s one thing for publishers to publish different philosophies, points of view,” said an editor at a different publishing house. “But he doesn’t really have a philosophy. He’s used the cloak of ‘I’m anti-PC,’ he finds different little phrases to justify his behavior, but … to pose as a provocateur as if it’s a political stance. That’s bullshit.”

Bellow, who is currently editorial director of an unannounced imprint for St. Martin’s Press (and, famously, something of a conservative firebrand), also passed on the proposal. His reasons were more complex. “From a strictly commercial point of view,” he told me, “it’s a no-brainer.” Yiannopoulos has a built-in following. Many people find him seductive and outrageous and interesting. “In the publishing industry, we’re accustomed to holding books at an arm’s length, out of what some would call cynicism, but I’d call it pragmatism,” Bellow continued. “We have corporate owners who review our quarterly earnings. So there’s an inherent bias, especially in larger companies, toward publishing whatever will sell.” Unsurprisingly, that is surely the soulless computation that Simon & Schuster made, according to more than a half-dozen people I spoke to who work in publishing, many of whom asked to talk off the record so as not to risk burning any bridges in the industry. “The calculus [of publishing Yiannopoulos] is not hard to justify,” said one editor, “if you’re just worried about selling a lot of books.”

But even though his imprint did not ultimately give Yiannopoulos a book deal, Bellow disagrees with Zackheim that Yiannopoulos’ lack of ideological substance is a problem. “He’s telling his story: who I am, where I came from, how I arrived at my beliefs,” he said. “He doesn’t need a systematic philosophy any more than the narrator of Hillbilly Elegy.” Nor does Bellow buy the argument that, unlike Coulter, Yiannopoulos’ particular brand of celebrity has little to do with the way he expresses himself in prose and that therefore he is a more troubling candidate for a book deal. Reading Yiannopoulos’ proposal, Bellow claims he detected evidence of actual thinking, that he “was pleasantly surprised” to find “an engaging, intelligent, educated voice” rather than “a hodgepodge of rants and Twitter insults.” “Nothing I saw led me to feel that the book was incendiary or dangerous,” he concluded. “I don’t see myself giving it to my girlfriend for Christmas, but Milo’s achieved some notoriety and his audience will be curious to know him better.”

In the end, the reason the St. Martin’s imprint turned Dangerous down was likely the same reason that Threshold picked it up: Doing so seemed like a shrewd business decision. Bellow’s unnamed new press aspires to publish voices from across the political spectrum. He worried that leading with Yiannopoulos would send the wrong signal to “serious, thoughtful people with passionate convictions on both the left and right.” “First acquisitions make a strong statement,” Bellow added. “My feeling about Milo was that if I’d had my imprint up and running for a couple of years, I would have personally been comfortable publishing him.”

Even when an editor enthusiastically goes to bat for a controversial book, a high-profile deal can easily be sunk by internal disagreement within a publishing house, because people all across the organization need to sign off before contracts get drawn up. While Bellow was working for the Free Press in the mid-’90s, the religious leader Louis Farrakhan submitted a book proposal. Though Farrakhan’s rhetoric wasn’t vastly more hateful than other screeds the house had unleashed, his anti-Semitism didn’t sit well with the predominantly Jewish editors, who rejected the application. And there was Judith Regan, another light of the conservative book business, who made her name working with the likes of Rush Limbaugh and Howard Stern. HarperCollins fired her, however, after she negotiated a contract with O.J. Simpson for the tell-all If I Did It, which higher-ups deemed over-the-line. (HarperCollins pulled the book, which Beaufort then published a year later.)

Neither Bellow nor other people in conservative publishing I spoke to feel that Dangerous in particular necessarily crosses an ethical line. In fact, some editors clearly believe that Threshold is honoring the First Amendment and shining welcome light on a liberal penchant for hysteria by elevating Yiannopoulos. The outrage over the book deal, said Anthony Ziccardi, publisher of Post Hill Press (and former editorial director of Simon & Schuster’s Threshold), “is a total overreaction—what about free speech?” Others simply locate in the memoir the apotheosis of a strand of titles that have long generated both controversy and sales, from Bloom’s 1987 salvo against higher education to Glenn Beck’s 2015 It IS About Islam. Of course, few of us exulting at or deploring Dangerous have actually looked at the manuscript. We’ll find out in March if it lives up to the hype.

*Correction, Jan. 18, 2017: This piece originally misidentified the conservative imprint of Penguin Randomhouse as Crown. It is Crown Forum. (Return.)