Bailey Jr. is a total stud-to-be. He has curly black hair, smooth dark skin, and he's just all-around good lookin'. And boy does he know it. Because of his good looks, Bailey Jr. is able to get away with everything. You know the type.
In case he wasn't perfect enough already, Bailey is also smart, graceful, and witty. Unlike Maya, he plays games with the local children and goes to the movies on Saturdays. He even leads the prayer in church sometimes. All he needs is an MD and he'd be every mother's dream. Don't you just hate him?
Unfortunately for Bailey Jr., all of these things aren't enough to attract the attention of his mother. When Maya and Bailey meet Vivian in St. Louis, Bailey Jr. falls head over heels in love. Who wouldn't? According to Maya's description, she's the most beautiful woman in the world.
When the sibs move back to Stamps, Bailey Jr. misses his "Mother Dear," and he has some interesting coping mechanisms. It starts with a little sarcasm. Then he starts watching movies with an actress that looks like his mother. (That sure doesn't help). Finally, he begins a relationship with a girl named Joyce:
For him, she was the mother who let him get as close as he dreamed, the sister who wasn't moody and withdrawing, and teary and tender-hearted. (21.24)
Love is so absent from Bailey's life that he looks for all kinds oflove—romantic, parental, sisterly—in one person. Is Bailey just trying to replace the love he never felt from his mother? If so, it's not working out too well for him.
In the end, how does Bailey Jr. escape the grips of his unrequited love for his mom? Once he and Maya move back in with Mother Dear, Bailey puts on a hyper-masculine show to compete with Vivian's friends who are conmen and pimps. In fact, it's his sad imitation of a pimp that causes Vivian to kick him out of her house and free him of his obsession with her. We're pretty sure his mommy issues aren't over, though.
Let's not forget that Bailey Jr. was black and male in the South when lynching was a real threat. While we're able to see many of the effects of racism through Maya's experiences, Bailey's presence gives us a glimpse into the violent side of things.
When Bailey comes home late from a movie one night, it's because he's seen a dead black man who had been killed by a white man—oh, and he was threatened and almost brought to jail for no reason. Things are so bad that Momma sends him and Maya to San Francisco. She has already raised two sons in the South, and she knows the dangers that lurk for him there:
A Black woman in the South who raises sons, grandsons and nephews had her heartstrings tied to a hanging noose. Any break from routine may herald for them unbearable news. (17.10)
Although Bailey Jr. experiences more violent racism than Maya, he reacts to it in a totally different way. When faced with the dead man, he shuts down and puts his soul to sleep. Maya can tell that something's off: "If he couldn't talk to me it must have been serious. But there was no air of spent revelry about him. He just seemed sad" (17.34). Maya, on the other hand, won't let racism stand in her way. Ever. Does Bailey Jr. get the short end of the stick? After all, he'd be risking his life by standing up for what he believes in.