In The Headmaster’s Dilemma, Louis Auchincloss revisits the prep school world of his most famous novel. That book, The Rector of Justin, published in 1964, took the form of a fictional biography, giving the reader the full life story of a much beloved and revered, if also feared, headmaster of an exclusive New England prep school. In The Headmaster’s Dilemma, we see up close what happens when a school’s ideals and founding principles collide with the exigencies of change.
The Headmaster’s Dilemma is the story of Michael Sayre, the handsome, avant-garde headmaster of Averhill, the great New England prep school as he is faced with a school administrator’s worst nightmare: a lawsuit brought by fervent parents in response to an incident involving their son and an upperclassman. To make matters worse, Michael is losing support from both the board of trustees -- led by the conniving Donald Spencer -- and senior faculty members. With the help of his supportive wife, Michael attempts to right these wrongs, while keeping Averhill’s best interests in mind.
From Publishers Weekly
Auchincloss sets his sights on a big, familiar target: the rich and shallow elite, and the peculiar troubles specific to them. In this case, the setting is Averhill, a New England boarding school. It's 1975, and headmaster Michael Sayre has a crisis on his hands: there's been a homosexual assault in the boy's dorm. His attempt to handle the matter quietly and fairly plays directly into the hands of sinister Donald Spencer, Michael's old classmate, chief nemesis and chairman of the board of trustees. Determined to ruin Michael's efforts to transform Averhill into a progressive institution (Michael initiates co-education, among other reforms), Donald foments outrage among the parents of the two boys involved and plots to force Michael's resignation and return Averhill to its stodgy old ways. The narrative flows smoothly, but the prose-especially dialogue-is pockmarked with linguistic anachronisms ("all wet," "pinkos," "what a lark!"), as if the novel has been sitting in a drawer for 50 years and underwent a hurried updating. Though old-fashioned feeling, this newest offering from a veteran writer (Auchincloss has published more than 60 books) entertains with its depiction of American aristocrats.
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From Booklist
New England prep school Averhill, a bastion of traditional WASP values, is changing with the times (it's the 1970s), thanks in large part to the popular and progressive headmaster Michael Sayre. Among his many assets is wife Ione, who, although she gave up her own career in law and now feels adrift, is steadfastly supportive. But Michael runs afoul of Donald Spencer, a member of the board of trustees, who wants to donate a grandiose sports complex. A former classmate, Spencer always resented the ease with which good fortune seems to attach itself to Michael, and dislikes the modernizations at the school. An opportunity to bring about the headmaster's downfall seems to present itself when a scandal erupts over a sexual incident involving two students, and parents and faculty start to question Michael's fitness for his role. The reliable Auchincloss may seem quaint at times, but he has an audience for his careful documentation of a rarefied world of manicured lawns and moral quandaries. Quinn, Mary Ellen