Presidential memoirs have historically been big gets in the book world. They fetch huge sums. Landing one is often a career high for editors and publishers. But the prospect of a new book by the current president, who may well be thinking about selling a memoir once he leaves the White House, is causing more agita than excitement at major New York City publishers. While it might be unheard of to turn down a title by a former American president, Donald Trump poses unique challenges as an author that could force him to go outside the confines of Manhattan to sell any prospective book.

PW talked with agents, editors, and other publishing professionals—most of whom spoke on the condition of anonymity, because the situation is both hypothetical and delicate—about the various reasons a Trump book deal would be far from straightforward.

The New York Post published an article suggesting that the president’s advance for a post–White House title could be as big as $100 million, but most sources PW spoke with said that number was much too high. Though few disputed that the president would ask for such a sum, a handful said they felt a more realistic figure was something in the $30–$40 million range. Many also spoke of the number that might loom large in any negotiation: $65 million, the sum Michelle and Barack Obama reportedly earned from Penguin Random House for their multibook deal.

While numerous sources said Trump would likely want a bigger advance than the Obamas, few felt the Obamas’ deal could be used as a benchmark, if for no other reason than the fact that the Obamas signed together for multiple books. (Whether Trump could post the same kinds of sales as either of the Obamas—Michelle Obama’s Becoming has sold more than 8.2 million copies across all formats in the U.S. and Canada to date—is an open question.)

Putting money aside, the biggest hurdle to a Trump book deal at a major house is the friction it could cause in an industry with a workforce and author base that leans decidedly left. Over the past three years, employees and authors have stopped two notable books from being released by their original publishers after publicly opposing them: Woody Allen’s planned memoir at Hachette and Milo Yiannopoulos’s book at Simon & Schuster. In the Allen case, employees at Hachette staged a walkout, and a number of S&S’s high-profile authors threatened to leave the house if it moved ahead with the Yiannopoulos book. Though sources said it was unclear what a protest against a Trump book might look like—employees working from home, after all, can’t physically walk off the job, and it’s debatable whether a former president, divisive though he may be, would inspire the same kind of backlash from authors—the possibility of it would weigh heavily over any potential negotiations.

Frank Breeden, managing partner at Premiere Authors, a literary agency that represents a number of conservative authors, thinks Trump would have no issue getting a deal. “There are some Big Five and significant indie editors who would definitely consider publishing a memoir from President Trump,” he said. “Some internal friction or action might arise among some employees and authors. But the same grounds that fueled the Woody and Milo decisions would not apply in this case, in my opinion. It would be hard for such efforts to be seen as anything other than viewpoint discrimination.”

Adam Bellow, a veteran of the conservative publishing space who’s worked at all the major houses and is now executive editor at Bombardier Books, a conservative imprint at Post Hill Press, said Trump deserves a deal at a large publisher but thinks it might not come to pass. “It’s a very difficult position for a big house to be in,” he explained. “Publishing is a business, and there’s no question Donald Trump will sell books. When I published Sarah Palin [in 2009], we sold 2.5 million copies of her book, and she was, at that time, the ex-governor of Alaska. Trump would, I guess, sell one million copies in his first week. So it’s a very compelling proposition for a publisher.”

Nonetheless, Bellow said, the attitude toward conservative books in the publishing industry has “shifted from contempt to outright hostility.” And this, he feels, might prevent the CEO of a Big Five house from green-lighting a Trump deal. “They will have a very difficult needle to thread, because there is the threat of attacks from without and rebellion from within. Then there’s the pressure from corporate owners to avoid controversy.”

All sources acknowledged that Trump doesn’t need a big publisher. He could self-publish (potentially releasing a book under the umbrella of a new Trump TV–esque conservative media venture) or strike a hybrid deal with a smaller player.

The latter is the option that Marji Ross, an industry consultant and former president and publisher of the conservative press Regnery, thinks Trump should pursue. She said that even if there were takers for a Trump book at the New York houses, which have all released books deeply critical of the president, he should go elsewhere. “Trump would be better off working with people who like him and are on his side.”

Who are those people? Ross pointed to Regnery (which is owned by Salem Media Group), Humanix (a division of Newsmax, which is owned by Trump’s friend Chris Ruddy), and Post Hill Press as possible landing spots. She said that during her time at Regnery the house did a number of hybrid deals that “Trump would be the perfect author for.”

Those who felt Trump could wind up at a Big Five house, if he chose that route, said he would land at one of the handful of conservative imprints. The question, as Bellow noted, is whether a CEO of one of the Big Five would sign off on a conservative imprint publishing the president. Despite the risks, a number of sources said one of the five CEOs will gamble on Trump. As one insider put it, “I think there will be a taker.”

Other sources said a book deal at a major house for the president may be complicated by the reputation of Trump the author more than that of Trump the politician. He has written, or cowritten, some 15 books over his career, publishing with every major house. And the difficult nature of working with him is well-known within publishing circles. Insiders said that in the past he has demonstrated a deep disengagement with the publishing process—both in the creation of and promotion of titles. Others, however, scoffed at this assessment, saying that a good ghostwriter can make any book work, and that the president can sell significant copies with a few tweets.

There may also be precedent for Trump to go his own way. Donald Trump Jr.’s Triggered was published by Center Street (the conservative imprint of Hachette) last November and sold 300,000 hardcover copies, according to BookScan. But his second book did not wind up at a big house: he self-published Liberal Privilege in September and, to date, BookScan reports just under 13,000 copies sold. (We did not reach out to Donald Trump Jr. for this story, but sources said the president’s son took meetings with some publishers about the title.)

All insiders acknowledge that the president has no shortage of publishing options. And many seem resigned to the fact that, despite what they want on a personal level, they can’t control what their industry does. “I think there will be hand-wringing and disappointment,” said one source, speaking to the prospect of a deal for Trump. “But I think people are pretty cynical at this point and understand that so many lines have been crossed already over the years that this is not any different.”

As another insider at a major house put it, “I’d say that freedom of speech should certainly justify publishing Trump’s book, but I shouldn’t be the one to do it. It’s hard to do a good job publishing something you don’t believe in.”