In the Prologue to My Losing Season, Pat Conroy writes that sports books are always about winning because those are more exciting to read. With this memoir about his 1966-67 Citadel basketball team, however, Conroy makes the argument that losing is a far better lesson for those involved. While he acknowledges that winning is wonderful, Conroy argues that “the darker music of loss resonates on deeper, richer planes” (14). The deep examination in the value of losing is an overarching theme running throughout My Losing Season. Winning, as the author points out, can spoil and pamper young athletes, leading them to believe that life will have no rough patches.

While My Losing Season is a chronicle of his basketball team’s entire season, it also examines Conroy’s time as a Citadel cadet and burgeoning writer and provides a biographical account of Conroy’s early years as they relate to his love of the sport of basketball. In looking at some of Conroy’s life before he arrived at The Citadel and some of his life away from the court, losing is a recurring aspect. As a military brat, Conroy’s family constantly moved, forcing him to leave schools that he had just gotten accustomed to and friends that he had just made.