Old School takes place at a prestigious American public school where the boys emphasize their democratic ideals. The only acknowledged snobbery is literary snobbery. Once a term, a big name from the literary world visits, and a contest takes place. The boys submit a piece of writing, and the winner receives a private audience with the visitor.

But then it is announced that Hemingway, the boys' hero, is coming to the school. The competition intensifies, and the morals the school and the boys pride themselves on—honor, loyalty, and friendship—begin to crumble under the strain. Only time will tell who will win and what it will cost them.