The Headmaster's Dilemma shows Mr. Auchincloss returning to the subject of his most famous novel, The Rector of Justin. Published in 1964, that novel 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 what happens when Michael Sayre, the handsome, avant-garde headmaster of Averhill, the great New England prep school, 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.