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John Colapinto, novelist and staff writer for the New Yorker, near his home on the Upper East side of Manhattan.Jonathan Lucas Auch/The Globe and Mail

In September, 2013, the editor Patrick Crean received a manuscript, entitled An Upright Man, which had recently been submitted to HarperCollins Canada, where he runs his own imprint. John Colapinto, the writer, was on staff at The New Yorker and the author of two previous books, one a New York Times bestseller – the sort of track record editors daydream about – yet, at the time the novel arrived in Crean's inbox, it had not found an American publisher. "I found that part very puzzling," recalls the Toronto-based Crean. "Why would this kind of book make people afraid to take it on?"

The answer as to why the book was causing so many editors pause came when Crean finally read the novel that weekend: faux-incest; sexual assault; borderline pedophilia; a cynicism that borders on unbearable. (It is also, perhaps unbelievably and distastefully, a darkly hilarious novel; one editor rejected the book because it was "too entertaining for its subject matter.")

"I have to confess that for about 24 hours I hesitated because the subject matter is such [that] it made me slightly uncomfortable," says Crean. "I wanted to really check in with myself to make sure this is what I wanted to put on my imprint. By Sunday afternoon I had really decided that this was so good that it needed to be published. I think there are times in book publishing when certain books ought to be published, and you kind of damn the torpedoes because they're important books. Because they're necessary books."

The novel, since rechristened as Undone, arrived in Canadian bookstores – and only Canadian bookstores – last week. Since September, 2013, Colapinto's agent, Lisa Bankoff, says the book has been read and rejected by 41 different American publishers.

"There was some preliminary interest in a handful of places, and then I'd hear that they didn't get the in-house support that was needed to go any further," says Bankoff. "I began to wonder if they were just being polite."

As impolite a book as you're likely to read this spring, Undone, in many respects, is a modern retelling of the Book of Job (God describes Job to Satan as "an upright man") and an "Aristotelian" tragedy about "a man who is actually undone by his own goodness, his own hubris, the thing that makes him best, which is his own virtue," as Colapinto put it during a recent interview.

And, like his previous novel, 2001's About the Author, in which an aspiring writer steals his deceased roommate's manuscript and passes it off it as his own, Undone is a novel about envy and the ways in which it corrodes and corrupts. That novel didn't "go far enough in confronting uncomfortable subject matter," he says on the phone from New York. "For some strange reason that's what I want to do when I write fiction." Still, even though he came up with the original idea not long after publishing About the Author, he put the idea aside for a long time. "I circled it warily for years," says Colapinto. "I was scared to write it."

The novel's structure is that of a bizarre love triangle. Dez, a thirtysomething former lawyer and teacher with a proclivity for teenage girls, is hiding out in a trailer park with Chloe, his latest conquest. An "ephebophile," meaning, in his case, he's attracted to teenage girls between the ages of 15 and 18, Dez has been in and out of jail (and therapists' offices) for a number of years, though he's reached a point in his life where he's at peace with his sexual preferences and cannot understand why society feels any different. Lying on the couch one afternoon, watching his favourite daytime talk show, Dez hears an interview with Jasper Ulrickson, a doting father and loving husband whose heartrending memoir, Lessons from My Daughter, has become a national bestseller. (The memoir chronicles Ulrickson's life with his wife, Pauline, who suffered a stroke giving birth to their first and only child and has been in a locked-in state ever since.)

Ulrickson is in many ways the antithesis of Dez – a man of "almost cartoonish or comical virtuousness," as Colapinto puts it (Ulrickson grows squeamish at the sight of a lingerie catalogue) and one who represents everything Dez has grown to hate about "the hypocrisy of a society that punished men like [Dez], men who had the courage to live out their animal nature, and exalted men like this Ulrickson, who could so convincingly masquerade as a dutiful, disciplined, decent male," as Colapinto writes in the opening chapter. It just so happens that Chloe's recently (and conveniently) deceased mother had a one-night stand with Ulrickson around the same time Chloe was conceived, leading the two of them to devise a plan for Chloe to pose as the famous author's long-lost daughter, infiltrate his family, seduce him and, when he's sent to jail, claim his fortune.

"I thought that the book was publishable," says Colapinto, 56, who was born and raised in Toronto and got his start writing for Saturday Night and other magazines, "but I'd be lying to you if I said I was unaware that I was going to be pushing publishers hard. This was – should I even be admitting it? Yeah, I should be admitting it – this was an act of some rebellion against the way I saw [how] things are. And you cannot do that without expecting that you might get rejected."

The number of times he was rejected still struck a nerve. The interview sometimes felt like a therapy session; Colapinto was at turns frustrated, saddened and bemused at the book's path to publication. Here is an author who, at least on the surface, has done everything right thus far in his career – a good agent, a solid track record, a job at The New Yorker – yet has been told again and again he'd written the wrong book.

Colapinto shared some of the rejections. One editor wrote that they were "very struck by how unsettling and powerful the book was, but there were worries that it might be a bit challenging to publish." Another said Undone was "just plain hard to wrap my head around with regard to audience. I'm aware of how wimpy that sounds – trust me, I've been avoiding this e-mail." Another felt the book "needs a less squeamish editor!"

"It was oddly predictable, but I still couldn't believe it was happening," says Colapinto.

"I was deeply disappointed, and I was shocked, and I was troubled. I was really, really, really troubled that they said, 'we can't do it.' And the ones that said that they thought it was masterfully done were more disturbing than the ones that just said, 'Oh, I'm too squeamish. It's too gross.' Those you go, whatever. But it's the ones where I could tell they considered it, they knew what I had achieved as a piece of writing and they still didn't have – the balls, is I guess the only way I can put it – that was really a disappointment."

Although he was careful not to compare himself, Colapinto says he found solace in the letters of Vladimir Nabokov, author of Lolita, a novel to which Undone will undoubtedly be compared. Now considered one of the great works of the 20th century, it was originally turned down by most of the major New York publishers before finding a home in 1955 with the "shady, semi-porno" Olympia Press in Paris. (Colapinto actually wrote his MA thesis on Nabokov while a student at the University of Toronto.) "I didn't for a moment pause to think how he felt when it was rejected by everybody," he says, referring to his youthful ignorance. "And I'm living through it."

Lisa Bankoff, his agent, says she has not given up hope of finding an American publisher. (The book has been sold in Japan.) She says "all or most" of the editors who read the manuscript are aware it has been released in Canada, and she hopes its release here will cause some to reconsider.

"No one has taken the bait as of yet," she says. "I don't think that this is the end of it, but the material has to speak for itself. And, so far, we haven't found the person who is listening hard enough."

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