Maya and Bailey’s father exemplifies ignorant, parental neglect. He is handsome and vain, and he speaks with proper English, almost to the point of caricaturing a stereotypical, upper-class white man of the time. Big Bailey ruins his own attempts to reconnect with his children, particularly with Maya. Absent from the children’s lives for years, he arrives in Stamps out of the blue one year, impressing the children and everyone else in town with his congenial nature and his fancy car and clothing, but Maya feels neither glad nor sad to see him go when they reach St. Louis. She regards him as a stranger, for he shows little genuine effort to care for her.

Though he resurfaces at the end of the book when Maya is fifteen and living in California, Big Bailey has not changed. Maya learns more about him—that he lives in a trailer park and suffers from many of the same troubles that afflict other Black men trying to advance in the world—but he fails to try to learn anything about Maya. Even though Maya enjoys seeing her father’s jubilant spirit in Mexico, the harsh reality of his selfishness continually undermines his appeal.

When first presenting him in the book, Maya questions whether Big Bailey obtains his possessions legally as a railroad porter or whether he advances through illegal means. At that point, he exemplifies the ethics of necessity seen elsewhere in the book, in which Black people compromise ethical behavior to break through the walls of racial injustice. Later, regardless of his methods, he exemplifies the tragedy of the American Black man trying to advance in a white society obsessed with class, paying more attention to his image than to his family.

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