An unnamed narrator details Cholly's childhood. At four days old, Cholly's mother abandons him on a junk heap. His Great Aunt Jimmy rescues him, and later beats his mother with a razor strap. Afterward, Cholly's mother runs away. Aunt Jimmy takes delight in telling Cholly that she rescued him, and besides the fact that she makes him sleep in the same bed with her in the winter where he sees her wrinkled breasts, he is grateful that she saved him.
This chapter allows the reader to understand what caused Cholly's dysfunction. Cholly has never had a sense of home and family, which sheds light on his inability to be a father. Even after Aunt Jimmy rescues him, he lives in a dysfunctional situation, where he lacks a father figure and is forced to sleep in the same bed as his aunt.
After four years of school, Cholly gets the courage to ask Aunt Jimmy what his father's name was. She tells him his father's name is Samson Fuller, and she thinks he ran off to Macon, Georgia. Cholly asks why he wasn't named after his father. Aunt Jimmy explains that his father was never around and his mother didn't give him a name, so she named him Charles Fuller after her deceased brother, who was a good man.
Cholly longs for a sense of home and family, which provokes his desire to know his father's name. Aunt Jimmy attempts to change Cholly's future by naming him after her brother, a moral man, and severing his connection to his father. Cholly, however, later names his own son Samuel, which is closely connected to his father's name, Samson, symbolically continuing the legacy of dysfunction in the family.
Two years later, Cholly quits school and takes a job at Tyson's Feed and Grain Store. At work he meets a man named Blue Jack. Cholly loves Blue Jack and enjoys Blue Jack's stories about what it was like during the Emancipation Proclamation. They also talk about the women Blue Jack has slept with, the fights he'd been in as a young man, and how he once talked his way out of getting lynched, while others hadn't.
Blue Jack becomes a father figure to Cholly. His stories about sex, violence, and racism are formative in the way Cholly matures into a man. The story about lynching demonstrates the dangers of being a black man, and shapes the way Cholly perceives his place in the world.
One July 4th, Cholly and Blue Jack are at a church picnic. The father of one of the families lifts a watermelon over his head, preparing to smash it on the ground. As Cholly watches, the man lifts the watermelon over his head. To Cholly his arms look taller than trees, and his hands look bigger than the sun. For a moment, Cholly wonders if God looks like the man with the watermelon, but he quickly realizes that God is an old white man, with a white beard and blue eyes. He realizes if the man does not look like God, he must look like the devil. Cholly decides that if the man looks like the devil, he prefers the devil to God. When the man smashes the watermelon, the watermelon's heart spills out. The man gives Blue Jack the heart and he shares it with Cholly.
Cholly associates God with whiteness, which furthers the theme of whiteness meaning virtue, cleanliness, and beauty. Yet by this logic, the black man must resemble the devil. This realization has a devastating effect on Cholly as a young black boy. Because he is black, he feels he can never attain the goodness of God, and therefor embraces his resemblance to the devil, and discards the desire to strive for goodness. By sharing the watermelon heart with Cholly, Blue Jack demonstrates his role as a father figure but the eating of the melon for Cholly becomes a kind of satanic ritual, an embrace of hating the white world.
During a very chilly Spring, Aunt Jimmy gets sick. Her friends pray for her and read the bible to her, but she still doesn't recover. Eventually, they decide to fetch a local medicine woman named M'Dear. Cholly is surprised when he sees M'Dear. He expected a decrepit old woman, but M'Dear stands six feet tall, and has four white knots of hair that give off a sense of power and authority. After running her fingers through Aunt Jimmy's hair and over her body, she asks to see the slop jar to examine Aunt Jimmy's stools. She instructs them to bury the jar, and tells Aunt Jimmy to drink only pot liquor.
M'Dear is one of few women in the novel with power. Her power comes not only through her physical size and appearance, but because she is independent and serves a necessary role in the community. She possesses knowledge that others in the community, including men, don't have access to.
Over the next few days, Aunt Jimmy drinks only pot liquor and improves. Her friends spend time with her, and Cholly listens to them as they talk nostalgically about the pain they have endured during their lives. These women, now elderly, have reconceptualized their experience in their own minds. In their understanding, instead of laboring in white homes, they ran the homes, and while they beat their children with one hand they took care of them with the other. As elderly women, they are beyond the lust of men, and therefor spared the dangers faced by younger women—they are "finally free".
The novel's black women only experience freedom from male oppression once they are no longer desired as sexual objects. By re-conceptualizing their experience, by re-telling their own stories, they come to fashion and understand the power they have always possessed as black women, caring for homes and raising children. Realizing this only after they are elderly, however, they are bitter because they have endured oppression their entire lives, never realizing their worth as young black women.
On a wet Saturday night a few days after M'Dear's visit, Aunt Jimmy eats peach cobbler, breaking the diet M'Dear prescribed to her. That night she dies. During the days after her death, Cholly does not immediately grieve her death. He receives a great deal of attention, food, a hot bath, and clean clothes. Before the funeral, Aunt Jimmy's family talks about how they will afford to bury her, and later decide that Cholly will go stay with Aunt Jimmy's brother.
The attention Cholly receives from his extended family prevents him from feeling the immediate gravity of his loss, although this loss will later have severe consequences. The discussion of burial costs demonstrates the financial instability of the family, but her brother's decision to take Cholly in demonstrates a sense of family still exists.
After the funeral, Aunt Jimmy's family and friends gather at her house. Cholly finds his cousin, Jake, outside of the house. Jake offer's Cholly a rolled cigarette, but when Cholly is unable to light it, he throws it on the ground. Ashamed, he feels he needs to prove himself, so when Jake asks if there are any girls around, Cholly says yes and leads Jake to where the girls are. The boys take a spot on the porch beside a group of girls and listen to them talk. The girls begin to bicker with one another as they react to the boys' presence.
Even from a young age, Cholly understands that women are a means to gain power and prove his masculinity. The way the girls' conversation changes in the presence of the boys demonstrates the power of male presence over women; the excitement of love and allure of sex. The girls begin bickering with one another, demonstrating the way that oppression turns the oppressed against one another.
Jake eventually persuades a girl named, Suky, to walk around with him. After Suky agrees, Cholly turns to another girl, Darlene, and tells her to come along. They walk to a wild vineyard, and eat muscadine berries. The boys begin chasing the girls, pelting them with grapes. During the chase, Darlene and Cholly slip into a gully, and when they pause to rest, they notice Jake and Suky are gone. Darlene grows concerned because her dress is stained and her mother is going to hit her when she gets back. Cholly realizes then that Aunt Jimmy is dead, and he misses the fear of being whipped.
Jake persuades Suky to follow him, while Cholly tells Darlene, as opposed to asking her, to follow, showing the power males have over females. Although pelting the girls with grapes is playful, the role of males as the aggressor and females as the victim is alluded to in this scene. Cholly's realization that he will miss Aunt Jimmy's beatings suggests his realization that the threat of those whippings kept him in line, kept him from tipping over the edge into something terrible. He recognizes, and fears, where he is going now that he is cut free of family.
Cholly feels sorry for Darlene and tries to help her tie the bow on her dress. As he ties the bow, Darlene slips her hands under his shirt and begins tickling him. Eventually they begin to have sex. During the act, however, Darlene suddenly stops moving and cries out. Cholly thinks he has hurt her, but quickly realizes that two white men with guns and a flashlight are watching them. The men force Cholly to continue having sex with Darlene. As he continues the sex act, the men humiliate him, shining the flashlight on his behind, and attacking him with racial slurs. Feeling powerless under their gaze, Cholly directs his hatred toward Darlene. Eventually, the white men hear their hunting dogs barking, and walk away.
Cholly's compassion and attempt to help Darlene shows that, at this time, he still possesses the capacity to be tender with women. Darlene makes the first move, indicating that the sexual interaction was consensual at first, and Cholly's concern when Darlene cries out further depicts his tenderness. The introduction of racial violence and oppression, however, immediately strips Cholly's ability to be gentle, showing the way that white oppression distorts black lives and leads to misplaced hatred.
Over the next few days, Cholly doesn't go far from the house, for fear of seeing Darlene. He continues to cultivate his hatred for her, never considering directing the hatred toward the white men as, subconsciously, he knows hatred toward the men he was powerless over would consume him because it would be a hatred he could do nothing about. One day while sitting on the back porch, Cholly develops the irrational belief that Darlene might be pregnant. He decides to run away and find his father. He knows that leaving Darlene is wrong, but in that moment he believes he knows how his father felt when he left. Cholly takes the money Aunt Jimmy had left in the stove flue and departs toward Macon, Georgia, to find his father.
Cholly knows that as a black man he is powerless over the white men who humiliated him. Hatred against them would consume him because there is nothing he could do with it. So he directs his hatred toward Darlene because as a male he has power over her, demonstrating a chain of oppression unfolding—the oppressed turn toward those who are weaker than them and become the oppressors. Cholly then follows in his father's footsteps by running, showing the way that familial dysfunction passes down generationally. He believes his father, who made the same decision, will understand why he ran from Darlene.
Cholly works odd jobs as he makes his way toward Macon until he's saved enough money to buy a bus ticket that would bring him the rest of the way. When he arrives in Macon, he finds a group of men gambling in an alley. Cholly is excited by the commotion in the alley and sight of the money being gambled away. He asks one of the men if he knows where to find Samson Fuller. The man points to Cholly's father, who is arguing with another man. Cholly is surprised that he is taller than his father, as he'd imagined his father would be a large man. When Cholly approaches, Samson turns and stares at Cholly. He asks Cholly who sent him. When Cholly can't remember his mother's name, he says nobody sent him, and tells Samson his name. Samson, having left before knowing Cholly's name does not recognize him. As Cholly walks away, Samson tells him to, "Tell that bitch she get her money."
Cholly finds his father gambling, drinking, and arguing with another man in an alleyway, which foreshadows Cholly's own bleak future. His excitement shows his attraction to that lifestyle. Cholly's idealized image of his father as a large, strong man, in whom he will be able to confide, is smashed upon meeting his father. Samson's lack of compassion and complete lack of recognition for his son, and likewise, Cholly's inability to remember his mother's name, shows the deep absence of family in these men's' lives. Samson's final comment depicts the way he imagines the women in his life—as freeloaders attempting to take his money.
In shock after the incident with his father, Cholly exits the alleyway and his legs give way. He takes a seat on a crate turned over on the sidewalk. Cholly exerts all of his energy to abstain from crying, but in the process, defecates in his pants. He runs to the pier and passes out in the shade beneath it in the fetal position. When he wakes up, it is dark and he begins washing his clothes in the river. He thinks of Aunt Jimmy as he cleans his clothes. Suddenly a longing for her company overtakes him and he begins to cry.
In attempting to retain his masculinity by not bursting into tears, Cholly defecates in his pants. In this moment, he metaphorically regresses into infancy, which is furthered by laying in the fetal position under the pier. This scene shows that even though Cholly goes to great lengths to prove his strength and masculinity, he is still a child. Eventually, he does cry, showing the pain he feels, not only over the loss of Aunt Jimmy, but at the loss of his dream of having any form of familial connection.
After this experience, Cholly finds himself dangerously free. He is free to sleep in doorways, sleep with women, beat them, and take care of them when he chooses. He is free to go to jail and not care, free enough to kill three white men, and free to drink himself silly. He doesn't care how long he lives or how he dies. When he meets Pauline, he is drawn to her by the joy he awakens in her. After he marries her, the repetitiveness of the married life makes Cholly desperate and uninspired. Alcohol becomes Cholly's only interest. He is dumbfounded about how to act once his children are born due to his own lack of a male role model growing up. He reacts to them based on what he is feeling in the moment.
As a black man unable to feel true freedom, his freedom comes at the expense of his concern for his life or the lives of others, which makes it a dangerous freedom. The happiness he brings to Pauline stops his dangerous behavior for a short time, but eventually his addiction to his "dangerous freedom" makes him comes to view marriage as another repressive force in his life, which makes him depressed and desperate for his old sense of freedom. His relationship with his children is marred by his own lack of family, and his old ways of acting and reacting based solely on his feelings (a very juvenile way of acting, unsurprising considering he has had no real adults in much of his life) has a devastating effect on his children.
On a Saturday afternoon, Cholly staggers home drunk. He finds Pecola at the sink washing dishes. As he watches her he experiences a fury of passing emotions—revulsion, guilt, pity, then love. He is revolted by her helplessness, then guilty because he knows he cannot take care of her. He can't understand how Pecola could love him, and in that moment he feels a deep hatred for her. As he watches, feeling a sickening hatred for his daughter, Pecola lifts her leg and scratches her calf with her toes. This gesture reminds him of the day he met Pauline in Kentucky. He is filled with tenderness for his daughter and desires to cover her foot and nibble her calf. Cholly drops to his knees and crawls toward Pecola. He begins nibbling her calf, and then pulls her to the floor and rapes her. As he finishes the sexual act, "His soul seemed to slip down to his guts and fly out into her." As he stands up, he looks at his daughter and feels a mixture of hatred and tenderness. The hatred prevents him from picking her up, so he covers her with a blanket and leaves her on the floor.
Depicting the rape through Cholly's perspective allows the reader to see how the damage of racism and racial self-hatred could allow this horrible act to occur within a family. Leaving Pecola's perspective out of the rape scene also demonstrates the silencing effect of oppression in women's lives. The fury of emotions reflects the damage that Cholly has accumulated in his life. The revulsion and guilt at Pecola's helplessness mirrors his first sexual experience with Darlene. His inability to feel loved suggests a deep self-hatred. The tenderness shows a longing to access the love he felt at first for Pauline. When he ejaculates, Cholly's self-hatred literally enters Pecola as she bears his child, the symbol of his ugliness and hatred, and metaphorically as she will carry the burden of this traumatic experience, which leads to her own self-hatred and self-perceived ugliness.