Flushed and apologetic, 39-year-old Andrew Trees arrives half an hour late at Feinstein’s, the librarylike bar at Manhattan’s Regency Hotel. Trees is the author of the recent novel Academy X, a satire of a prep school. The book almost surely cost him his job teaching history at real-life Horace Mann, one of New York’s most prestigious private schools and a steady source of Harvard freshmen. While Trees says it was generally “a very easy place to teach,” his final days there were “very unpleasant.” So, in November 2007, Trees filed a lawsuit against Horace Mann for $3 million, charging it with breach of contract and defamation. Throughout our meeting, he is watched by his ever-mindful attorney, Thomas Mullaney, who heads his own self-named New York firm.

Trees, the son of an investment consultant, is no outsider to privilege: He was educated at Deerfield, Princeton, and the University of Virginia, where he earned a master’s in English and a history Ph.D. He joined Horace Mann’s history department in 2001, and relished the work. “Every year there was one, maybe two students, who seemed ready not for college, but for grad school,” he says. With an enrollment of about 1,750 students in 12 grades, the school sent 42 students to Harvard between 2002 and 2006, and counts Eliot Spitzer, Robert Caro, and James Murdoch among its alumni.

But Trees also discovered a culture in which students, parents, and faculty were obsessed with admission to Ivy League schools. Although he followed a prep-to-Princeton path over 20 years earlier, he says, “I don’t remember thinking about where I was going to go to college until the second half of junior year. The kids at these schools think about it in middle school.” Trees came to feel that the endless grind of SAT courses, credential-boosting summer camps, and competitive volunteerism was killing students’ intellectual curiosity; they lacked the time to engage in academic exploration, and they did not believe that such activity would help them get into Harvard. “There’s a real psychic cost for the pressure they’re under,” Trees says. “It’s difficult for them to have a childhood.” In 2003, Trees began writing a novel.

The protagonist of Academy X is John Spencer, an English teacher at an unnamed New York City school who observes “an ethical wonderland.” Academy X’s college advisory office has a creepily cozy relationship with Ivy League admissions offices; its administration ensures that the children of deep-pocketed parents, no matter how dim, gain admission to their school of choice; its teachers must lubricate these dirty deals with embellished grades and recommendations. When Spencer catches one student plagiarizing, endangering her acceptance at Princeton, she accuses him of sexual harassment. Complications ensue.

Published by Bloomsbury, Academy X came out in June 2006. According to its publisher, the book was “a priceless peek into New York City’s top private schools … where parents risk all for their child’s academic resume and no price is too high (or pressure too great) to achieve a coveted admission to Harvard, Yale, or Princeton.” Critics quickly lumped it in with The Nanny Diaries, Prep, the Gossip Girl books, and an entire genre that pokes fun at the privileged. The novel received mixed reviews, and as of the beginning of this year had sold about 7,500 copies since its release—perfectly fine for a debut work of fiction, but nothing like the massive success of those earlier thinly veiled tell-alls.

For some at Horace Mann, though, how widely read Academy X was may not have mattered; Trees’ story felt uncomfortably close to home. In January 2007, Head of School Thomas Kelly called Trees into his office for an unscheduled meeting and informed him that he would not be teaching at Horace Mann come September. “It came out of left field for me,” Trees recalls, still sounding genuinely mystified at the idea that his book could cost him his job. “I was getting this incredibly positive review of my job performance, yet I was being told that my contract wasn’t going to be renewed.”

Trees was a popular teacher, and his dismissal inspired walkouts on campus and an editorial in the school paper, The Record. “[Our] institution is likely about to become the first independent school in America to dismiss a teacher for having published a novel,” lamented fellow history teacher Peter Sheehy. (Sheehy declined to speak with 02138, as did other Horace Mann officials and faculty.) The Record—which the Horace Mann administration controls—rejected another protest letter, signed by nearly 70 academics, some of them alumni or parents of alumni. It subsequently appeared in the New York Times. Horace Mann remained unmoved.

Trees’ supporters may be upset about his dismissal, but they’re not exactly surprised by it. “These schools are so close to the power structures,” says Victoria de Grazia, a history professor at Columbia and a Horace Mann parent who signed the letter printed in the Times. The politicians and captains of industry who send their children to Horace Mann “boss their households around; they boss their corporations around—why shouldn’t they be able to boss the school around? The school knows that.” Those on the other side suggest that Horace Mann has no obligation to continue employing someone who is throwing dirt at its pristine reputation.

As he waits for his case to progress—it is expected to go to court imminently—Trees is getting by on the advance for his next book, a nonfiction work about dating, and income from his wife, a graphic designer. He’d like to work as a teacher again but thinks it unlikely—at least, not in the private-school community. He has learned that he would rather not be a full-time writer. “Writing full time makes you a little crazy,” he explains. “I loved being able to go in every day and teach.”