Due to the episode with the knife, Granny and Addie give up on saving Richard’s soul and he is permitted to return to public school, though Granny refuses to pay for his non-religious books. He wears a straw hat to school on his first day of fifth grade, and fights two boys after it is knocked off his head, thus proving himself, yet again, with his fists. But for perhaps the first time, he also demonstrates his abilities in the classroom, and is promoted to the sixth grade within his first two weeks. Because he is not allowed to work Saturdays due to Granny’s religious beliefs, Richard cannot find a job and joins his peers buying snacks at the corner store at lunchtime. He disguises his poverty from his would-be friends, secretly longing to belong to their group. A classmate offers him a job selling newspapers, confessing that he hasn’t read them himself, but adding that he enjoys the magazine supplement. Richard unhesitatingly orders some of the Chicago-printed papers himself, excited to not only have found a solution to his pennilessness, but to be able to access new reading material as well. However, a black customer soon takes Richard aside and asks him about the paper’s content, which includes cartoons and articles backed by the Ku Klux Klan and that voice clearly anti-black sentiment. Outraged, Richard stops selling the paper, and learns that his classmate’s father has also forbidden him to sell it. Ashamed and embarrassed, the two never discuss the matter. Richard again is hungry, for without the income from his paper route he cannot buy food or socialize with his peers.
One day on the front porch, Richard interrupts a religious discussion with a comment that makes Granny so angry she loses her balance trying to slap him, and falls down the stairs. Addie blames Richard for her mother’s back injury, and threatens him in the hallway. He again resorts to a kitchen knife in defense, sleeping with it under his pillow lest he need to fend off his aunt in the middle of the night, an idle threat she never follows through on. But Richard considers the supposedly religious household more violent than that of a gangster or burglar.
The illiterate insurance salesman next door offers Richard a job writing for him, and the two visit the local plantations where Richard witnesses the seemingly universal poverty of Southern blacks. He is alarmed to feel like a cosmopolitan city dweller compared to the shy children he encounters, who relative to him, are as ignorant as their parents.
Grandpa’s health worsens as his frustrations with claiming his pension for serving in the Civil War continue. Apparently due to a misspelling of his name, whether intentional or not, he has fought for decades with the War Department to no avail. Bitter and angry, Grandpa dies without convincing the authorities of his service, remaining estranged from his family as a result. Richard is sent to inform Uncle Tom of Grandpa’s death. After running the whole way, Richard wakes his uncle and without softening the news tells him his father is dead. Tom is horrified at Richard’s lack of tact, and Richard reflects on how he never seems able to please people.
As his clothes disintegrate and he is too self-conscious to wear them to school, Richard threatens to move out if he is not allowed to work on Saturdays. Granny relents and lets him work, but makes it clear he is now dead to her. His mother is proud to see Richard stand up to her mother and sister.
Richard takes on several complex challenges in this chapter, including the decision to return to public school even though he has no means to pay for books, which Granny insists come from his own pocket despite her unwillingness to let him work on Saturdays. Freedom from Addie’s oversight is nevertheless an important enough reason for Richard to take the risk, and he is overjoyed to meet peers at the corner store with coins in his hand earned from his paper delivery job. However, despite his economic and social dependence on this job, when a black customer shows him that the Chicago-based paper is guilty of the most offensive propaganda, he does not hesitate to quit. Horrified to have been working against his own interests out of ignorance, Richard resolves to educate himself and never again contribute to the killing of his own community, as this father figure gently but strongly warns. Richard’s visits with another benevolent black man, Brother Mance the insurance salesman, similarly show him the injustice of the world around him. At some level he identifies with the desolate poverty of the sharecropper life, the son of a sharecropper himself, feeling well off by comparison with the illiterate and ignorant clients. The power of literacy is further demonstrated by Grandpa’s endless battle with the War Department over his pension, as a small clerical error has disenfranchised him to the point he dies a broken man, having failed to prove his record as a soldier for the Union army, which ironically fought for the rights of free blacks like himself. Richard further suggests that a rumor that a white officer intentionally misspelled his grandfather’s name merits consideration, stressing the point that even “official” government entities can all too easily take advantage of illiterate citizens.