The protagonist is alone in his room with his seven letters of introduction. He is tempted to open them but dismisses the thought. He envisions himself one day to be like Dr. Bledsoe and heads out to the Wall Street District with the thought that this opportunity will put him in the position to achieve that dream. His first stop is the office of Mr. Bates. He gives his letter of introduction to the secretary. Bates declines to see him, and the protagonist, although disappointed, continues to the other offices delivering his letters. This also gives him an opportunity to see the city. During his travels, he attempts to reconcile the difference between how whites treat him in the north as opposed to the south. He comes to the conclusion that he is invisible to them and this is why they are not overly concerned with him or rude to him.
He has distributed all his letters but one and it is addressed to a Mr. Emerson. The protagonist also decides to write Mr. Norton but time passes and he never receives a reply. The chapter ends with the recurring dream of his grandfather and his words. The protagonist becomes concerned and desperate to hear back regarding his letters. He eventually receives a letter from Mr. Emerson.
The chapter opens with the protagonist heading to his meeting with Emerson and thinking about the old days at the campus. He retains the hope that things will work out. On the street, he runs into an older man, who is singing the blues and pushing a cart full of rolls of blueprints. The man strikes up a conversation with the protagonist and immediately realizes that the protagonist is from the south. The protagonist attempts to dissociate himself from the man but the man pursues further and asks a pointed question: "Why you trying to deny me?" The protagonist, troubled by the question, lingers on to talk to the man. The man informs him that the blueprints are for country clubs, homes, and various plans for different kinds of buildings. He ends by quoting excerpts from Negro folk tales and rhymes. The protagonist contemplates the man's words and his interaction with him.
The protagonist then goes to get breakfast. He refuses the special of pork chops and grits and later notices a white man eating the pork chops and grits breakfast. After breakfast, he arrives at Emerson's office. There, he notices an aviary of tropical birds that are confined in the office. A gentleman approaches and begins questioning him. The man is Mr. Emerson's son, who carries on a conversation with the protagonist and attempts to establish a connection with him. He compares their relationship to Jim and Huck from Mark Twain's Huckleberry Finn. Eventually, the protagonist is able to give his letter to the young man. When the young man reads it, he is angered and shows the letter to the protagonist. There, the protagonist reads Dr. Bledsoe's true sentiments. Bledsoe has informed these businessmen that the protagonist has been expelled and shall never return to the college and ends with a plea for some degree of consideration even though it is clear that after the disparagement, this will not occur. The protagonist is shocked and deflated. He begins to question himself out loud. Young Emerson, in sympathy for the protagonist, invites him to a party and also recommends him for a job at a company called Liberty Paints. The protagonist leaves, confused and shocked. He reflects on the words of a familiar song "They picked poor robin clean." He feels angry and later that night dreams of enacting revenge.
These chapters are important because the protagonist is beginning to understand the situation he is truly in. He has seen the contents of the letter and realizes that there is no hope in returning to the college. He also struggles with identity and his shame because he desires to distance himself from some elements of black Southern life, such as the food.