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 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.