Conroy begins part 2 of My Losing Season with Chapter 4, “First Shot,” which detours from his straightforward account of the 1966-67 season to discuss his uprooted childhood, when he fell in love with basketball, and his turbulent high school years. Conroy describes the year he spent living in Orlando, Florida as the happiest of his childhood. This was at least partially, according to Conroy, because his father spent the year on an aircraft carrier in the Mediterranean. The chapter also introduces readers to his father, Donald Conroy, a Marine Corps fighter pilot who was extremely abusive toward his family. Donald had been a standout basketball player himself during his high school years in Chicago and later at a small college in Iowa. Conroy laments the fact that his father did not pass along his knowledge of the game to him and that he continually diminished his accomplishments by comparing them to his own. Conroy writes: “his greatness as a ballplayer was thrown in my face each time I achieved some new milestone as a player” (47).

Following their year in Orlando, the Conroy family relocated to Arlington, Virginia, then to Belmont, North Carolina, then to Washington, DC.