Richard passes the postal examination in the spring and befriends an Irish clerk who shares his cynicism for the communists and other politically active factions in the city. Richard is fascinated by the Garveyites—blacks attempting to return to Africa—and despite his view that their goal is unrealistic, likes and respects their strength. Unemployment is on the rise, and rather than being appointed a regular clerk, Richard receives fewer shifts until finally the full effects of the Great Depression require him to take a job selling insurance policies to poor blacks. Like the other agents, he takes to sleeping with a woman who can’t pay in any other way, though is disgusted by her illiteracy and ignorance. He agrees to take her to the circus anyway, but judges her and many black men and women in the community who seem obsessed with sex and sexual relations. Crossing Washington Park and seeing the protesters threatening revolution, he taunts some communist organizers who believe the masses will revolt if Hoover removes them forcibly. Richard also marvels at the militant atheism he witnesses, and turns his own criticisms to the imperfections of American democracy. He agrees to help a local politician round up votes for the extra money, but on his own ballot writes “I Protest This Fraud” so the counters will at least know one voter is aware of their corner-cutting. Without work, he sells some belongings and moves to such a dismal apartment his mother weeps upon seeing it. Although too ashamed until this point to collect relief from the Bureau of Public Welfare, having reached a low point Richard joins the masses waiting for bread rations.
Just as in the South, in Chicago Richard is unable to fully identify with any social group, and he remains as much of a loner as ever. He is interested in the Garveyites and their optimism for a return to Africa, but he cannot reduce himself to belong to their club or any other. Richard defies definition and feels most blacks he meets in Chicago are obsessed with sex, and in fact some of the whites as well. As an insurance agent, Richard falls in with the very crowd he despises for their unethical behavior, both professionally and sexually. He is distraught by his own participation in a scheme to switch policies, duping poor black clients but unable to leave the job without risking starvation. He is careful to explain that the alternative to this job was clearly starvation, and that his principles did not require him to starve himself and his dependent family members. His previous experiences with theft and lying similarly revealed Richard to be a person of principle, and thus being reduced to his present situation, especially having achieved his goal of moving physically North, is a double blow. An aura of illness, misery, foreboding and despair haunts the final paragraphs. He simply cannot sink any lower. His shoddy apartment prompts tears from his hopeless mother, and he joins the masses in the breadline with a tone of defeat.