Aunt Pooh, Bri’s aunt and Jay’s sister, is a source of love, support, and guidance for Bri. Pooh introduces Bri to hip-hop, gives her advice, and acts as one of the biggest supporters of Bri’s rap career. Bri calls Aunt Pooh “Yoda,” accepts her financial help, and reaches out to her when she is in trouble. However, Aunt Pooh’s loyalties are split between Bri and the Garden Disciples gang, of which she is a member. While Jay and Trey play by society’s unfair rules, struggling in poverty, Aunt Pooh resorts to a life of crime, in effect becoming the stereotypical “hoodlum” that Bri resists being labeled as. As a drug dealer who Bri suspects has committed violent crimes, Aunt Pooh is deeply involved in the power struggles and constant dangers of gang life.  

Aunt Pooh does not seem to endorse her own life choices. When she hears Bri wrapping about gang life in "On the Come Up," she is angered and disturbed. Unlike Supreme, she tells Bri to be true to herself and flatly tells her to delete the song. But Bri loses trust in Aunt Pooh as her manager because she is unreliable, abandoning Bri at her first recording session and regularly disappearing for days at a time. Though she says she supports Bri and wants to help her get out of Garden Heights, Aunt Pooh cannot extricate herself from gang life. At the novel’s end, Aunt Pooh is in jail, trapped both by the law and by her obsession with the gang war, unable to focus on what she needs to do to save herself. In this way, Aunt Pooh serves as a cautionary tale for Bri. While Pooh’s intentions are good, she can't escape the consequences of choosing to be what society expects her to be.