Skippy is the tragic hero and one of three protagonists in Skippy Dies. Because the novel opens on the titular event of his death, most of the narrative action orbits around the causes and effects of his death. Though he dies by suicide from an overdose of drugs, there are several factors that plausibly contribute to his death, including the self-imposed silence around his mother’s cancer; sexual abuse at the hands of his swimming coach; the secret relationship between his crush, Lori, and his bully, Carl; and the anger of his history teacher, Howard Fallon.

Skippy begins the narrative as an anxious student who relies on painkillers to pacify his anxiety throughout the day. His overdependence on drugs causes him to throw up in class, which garners the attention of various school authorities, including the principal, Mr. Fallon, and Father Green, whose class he throws up in. Skippy panics after Father Green touches his face in a way that reminds him of his molestation, a feeling that is exacerbated when Mr. Fallon checks in on Skippy at school. He nearly runs away from Seabrook, only to stop when he sees Lori for the first time playing frisbee outside his window.