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 the support of 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.