The first book in the series was written when Korman was in Grade Seven. The briefest of the series, the book introduces the school and its boys. Bruno and Boots are separated as roommates after committing three pranks at the hockey match against their arch-rival, York Academy; Bruno moves in with Elmer Drimsdale, the school genius, whereas Boots moves in with the school financial genius and resident hypochondriac, George Wexford-Smyth III. The boys scheme to convince Mr. Sturgeon ("The Fish"), the headmaster, to allow them to move back to Room 306.