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The narrator is walking along to his appointment with Mr. Emerson when he encounters a black man pushing a shopping cart and singing the blues. The man reminds the narrator of home, but also disturbs him much like the Golden Day veterans had disturbed him. The narrator feels himself smiling at the man's rhymes, wondering what they really mean; he also thinks of the freedom the man has in this city. The narrator, however, determines he will not become too attached to New York, for he plans to return to school and believes that his experience in the city will make him better prepared for college. Entering a diner to have breakfast before his meeting, he finds the service insulting. When he leaves, the narrator wonders if a tip from a black man to a white waitress would be insulting.
The narrator goes to Mr. Emerson's office and hands his letter to a young man who appears to be the secretary. He is then interviewed briefly by this man, who turns out to be Mr. Emerson's son. The younger Mr. Emerson gives in to his impulse and shows the narrator the letter that Dr. Bledsoe has written. It says to the addressee to please help sever this former student's ties to the college because of crimes he has committed. The younger Mr. Emerson wants to help somehow and suggests that the narrator look for employment at Liberty Paint. The narrator is too shocked about the letter to listen to the suggestion; he quickly leaves the office.
Out on the street, the narrator begins singing a folk song, again wondering about its meaning. He begins drawing connections between his life and the fate of the Robin in his song. Anger over Dr. Bledsoe fills him, and he dreams of getting revenge; however, he decides he must first find employment. He successfully applies for a job at Liberty Paint and is told to report to work early the next morning.
At the beginning of this chapter, the naïve and hopeful narrator hears a black man singing the blues and wonders what the lyrics to common folk songs mean. Although he knows them by heart, he does not understand them. After he encounters the young Mr. Emerson and the truth of Dr. Bledsoe's letter, he can no longer fight disillusionment. After experiencing this shock, the lyrics to the folk songs he sings begin to make sense to him. He recognizes himself as the disenfranchised subject of the common folk song.
Though it is not yet clear to the young narrator, there is an obvious connection between the letter written by Dr. Bledsoe and the letter he dreamed about the night of the Battle Royal. Both letters state that it is best to keep this young "nigger" running.