When I Was the Greatest begins with first-person narrator Ali and his friend Noodles playing a game of “Would You Rather?” Ali then talks about his mother, Doris Brooks, who is a tough but loving parent working two jobs to support their family in a gentrifying Bed-Stuy, Brooklyn. He describes a neighborhood with “the guns and drugs and all that” (8) but says he prefers to focus on school and staying out of trouble.

He recounts meeting brothers Needles and Noodles, who moved in next door five years earlier. He describes an “exhausted” Noodles who is reluctant to admit where he lives, but eventually does. Ali is surprised Noodles lives next door because prostitutes and drug addicts inhabit that building. Ali tells Noodles it’s okay to sit on his stoop, and after they sit together a while, Doris calls them both in for food.

Ali explains his and Noodles’s nicknames, which both came from Ali’s younger sister Jazz. Ali’s initially poor boxing technique got him mockingly nicknamed after Muhammad Ali, while Noodles was named after he was caught kissing a girl with his lips puckered as if “slurping spaghetti” (16). Ali meets Needles about three months after meeting his brother.