Maya’s older brother by one year, Bailey is the most important person in Maya’s life throughout her childhood. When moved around from place to place, Bailey and Maya depend on each other to achieve some semblance of stability and continuity in their lives. Unlike Maya, Bailey is graceful, attractive, outgoing, and charming, and many consider him the jewel of his family. Bailey uses his skills and status to protect Maya. With his charms, he defends her against criticism and insults. Bailey and Maya share not just in tragedies but also in private jokes and a love of language and poetry.
One of the most striking differences between Maya and Bailey is their ability to confront racism. Bailey explains to Maya early on that when he senses the negative effects of racism, he essentially puts his soul to sleep so that he can forget the incident. Maya, however, learns to resist racism actively. Bailey and Maya grow further apart as they go through adolescence, and Bailey continues to withdraw deeper into himself. Even so, Maya continues to confide in him, asking for advice about her pregnancy. He continues to show his love for her as well, replying quickly to his sister and giving caring advice.
The return to Stamps from St. Louis traumatizes Bailey, and though he never blames his sister, he remains tormented by his longing for his mother. He expresses his longing through moodiness, sarcasm, and a bold assertion of his independence. In Stamps, he finds outlets for his longing for maternal affection by watching the white movie star who looks like Vivian and by playing “Momma and Papa” with Joyce, his buxom girlfriend who is four years his senior. In San Francisco, Bailey tries to win his mother’s approval by imitating the people she befriends—he becomes the pimp-like boyfriend of a white prostitute. Bailey moves out at age sixteen and gets a job on the Southern Pacific Railroad, explaining that he and Vivian have come to an understanding with each other and that he has grown wise beyond his years.