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.