On a sunny day, the narrator sets out to meet Mr. Emerson. He wonders what is going on back on the college campus, and suddenly feels sure that something good will happen that day.
Emerson’s letter has temporarily convinced the narrator that he will resume his old life at college after earning his tuition.
Near the curb, the narrator sees a man with a cart full of blue papers. The blues man is singing an old blues song that compares the body parts of his loved one to animals. When the narrator comes alongside him, the blues man asks him a strange question: “Is you got the dog?” The narrator is unsure how to answer the question, and the man implies that the narrator should know, as he’s also from down south.
The blues man addresses the narrator with traditional black banter, a reminder of the cultural background that the narrator has in many ways forsaken. Both his banter and the blues he sings are the products of a culture that has learned to express its sorrow in a covert way.
Exasperated, the narrator finally replies that he doesn’t have “the dog.” The blues man tells the narrator not to get mad, as he thought that the narrator was trying to “deny” him. He says that maybe the dog has a hold of the narrator instead, and that he himself has got “the bear” clawing him. He calls Harlem a “bear’s den,” but also “the best place in the world for you and me.”
The narrator is unable to return the blues man’s banter, and becomes angry at what to him seems like silliness. “The dog” and “the bear” are expressions for hardship and trouble. The blues man indicates that Harlem is both a trying place and a haven for black people.
The narrator asks what the blues man is doing with all the blue paper. The man replies that they’re real blueprints, even though he can’t build anything with them. The man says that people are always changing their plans, to which the narrator replies, “You have to stick to the plan.” The blues man introduces himself as "Peter Wheatstraw [...] the Devil's only son-in-law" and continues with his banter, which the narrator begins to like, although he does not know how to reply. The blues man departs, singing his blues as he walks off.
The blues man’s blueprints are representative of the many possible future plans that have gone unfulfilled. The blues man collects these possibilities, making him a repository of both past intentions and future actions. The narrator, who still believes in a simple path of ambition, is unable to see the power of the blues man’s flexibility. Peter Wheatstraw is a name from folklore and was also a famous blues musician in the 1930s.
The narrator reflects that he’s heard talk like the blues man’s all his life, but only now noticed how strange it really is. He notices the musicality of the blues man, thinking about the strangeness of the song and its lyrics, and for a moment feels proud of his race.
For the first time, the narrator begins to have an appreciation of the power of his own roots and culture. The musicality, cleverness, and resourcefulness of the blues man are all responses to a history of hardship.
The narrator enters a drugstore for breakfast. The man behind the counter offers the narrator a special of pork chops, a southern dish. The narrator, taking offense to being automatically seen as southern, orders a plain meal of orange juice, toast and coffee. The narrator hopes he will be a little different when he returns to school.
The narrator is still searching for a transformation of himself in New York, and wishes to believe that he is not automatically perceived as southern. However, changing his breakfast order is a sign of the superficial way the narrator perceives his change.
The narrator thinks about Dr. Bledsoe, noting that the students never know how he acts when he’s away from campus. He thinks that this difference is part of what makes Bledsoe a good leader, as “he was never out of our minds.” Finally, the narrator thinks that maybe he knew this all along. As he leaves, the narrator notices pork chops being served to a white, blond man.
The narrator begins to understand the difference between appearances and reality. Dr. Bledsoe is able to maintain the appearance of ease and power by concealing his activities away from the college. The blond man undercuts another assumption by the narrator about appearances—the blond white northerner is eating a meal the narrator thought would mark him as too southern.
The narrator arrives at Mr. Emerson’s office. He inspects the office, which is filled with a huge map and exotic oddities from around the world. The narrator assumes the business must be an importing company. A blond man with glasses (young Emerson) asks the narrator what his business might be.
Mr. Emerson’s office indicates the global power exercised by the white elite. A man like Mr. Emerson almost effortlessly creates change throughout the world, a level of power into which the narrator now has a brief window.
The narrator explains his appointment and hands young Emerson his letter. Young Emerson leaves with the letter and the narrator goes back to inspecting the room, noticing Chinese statues and an aviary of tropical birds. Young Emerson seems to be reading Freud’s Totem and Taboo. Certain items in the room remind the narrator of relics from slavery times in the college museum.
The narrator is reminded of his college’s relics of slavery, and this comparison makes it clear that the exotic items in the room are the product of a power that is capable of subjugating and exploiting other cultures. Men like Emerson take what they want for their own economic gain.
Young Emerson returns and invites the narrator into his office. He sits down and asks the narrator what it is he wishes to accomplish. The narrator tells him he wishes to get a job in order to return to school. Young Emerson asks the narrator more questions, including his age and what he thinks of his college. He asks the narrator what he would think of transferring, and the narrator says reluctantly that he’s never thought of it.
Young Emerson is the first white person in New York from the elite who has spoken with the narrator. Young Emerson seems sincerely interested in the narrator and his ambitions, but is deeply skeptical of the narrator’s continued attachment to his plan to return to the black college.
When asked, the narrator tells young Emerson that his career goal is to become Dr. Bledsoe’s assistant. He asks the narrator how many letters of introduction he was given, to which the narrator tells him seven. Young Emerson is clearly displeased, but the narrator can’t seem to figure out why. Young Emerson mentions that he has just had a difficult session with his analyst.
Young Emerson frequently mentions his analyst, indicating that he is concerned with a type of psychological self-examination that is previously unknown to any character in the novel. However, while he wishes to help the narrator, it implies that his motivation for doing so may be self-interested, a form of self-help .
Suddenly, young Emerson asks the narrator if two strangers can speak to each other with total honesty. The narrator doesn’t understand the question. Young Emerson tells the narrator he must disillusion him, as there is a “tyranny” involved in his request for a job. The narrator doesn’t understand, and simply wants to see Mr. Emerson (the trustee) and have a word with him.
Emerson’s request that he and the narrator speak with each other honestly is ultimately impossible. Both men have too much invested in their own disparate narratives of life. In many ways, the narrator cannot be honest with himself, holding onto the dream of Dr. Bledsoe’s letters.
Young Emerson tries to give the narrator advice, but the narrator doesn’t want to hear it. Young Emerson tells the narrator not to go back to the south, as there is more freedom in New York City. He tells the narrator that it would be “best” for him to forget college all together. The narrator begins to get angry, blaming young Emerson for not letting him see Mr. Emerson. Young Emerson reveals that Mr. Emerson is his father.
Still under the impression that Dr. Bledsoe wishes to help him, he accuses young Emerson of being self-interested in refusing to let him see Mr. Emerson. It seems that there may be something true to his self interest: young Emerson has cast the situation as a psychological struggle against his father.
Unable to convince the narrator any other way, young Emerson opens the letter of introduction and lets the narrator read it. Dr. Bledsoe’s letter instructs Mr. Emerson to mislead the narrator, allowing him to hope that he will return to school when it is no longer possible. The narrator is dumbstruck by the news that the letters were intended to impede him. The narrator says he only wanted to return to college, but young Emerson tells him he can no longer do so.
By letting the narrator read Bledsoe’s letter, young Emerson severs the narrator’s last hopes of returning to the black college. It has turned out that Bledsoe has acted far more perniciously than previously thought. The result is a deep disillusionment for the narrator.
Young Emerson tries to offer the narrator a job, first as his valet, then mentioning an opportunity at Liberty Paints. The narrator, dejected, turns him down. To the narrator, the entire situation seems like a joke. As he returns home, he hears a familiar tune, an old song about tying up a robin and plucking him. The narrator starts humming the tune and soon compares himself to the robin.
It is unclear if young Emerson’s offers of help are truly altruistic or if they are motivated by an obscure sense of guilt. The narrator, shocked, discovers that his entire trajectory since the beginning of the book has been misguided. The song of the robin helps remind him that he has roots beyond the college.
The narrator wonders if young Emerson had an ulterior motive of his own, as everyone else seems to have one. At home, the narrator is filled with anger toward Bledsoe. He begins to laugh and plot his revenge, telling himself that this time he will make the first move. He calls Liberty Paints, as mentioned by young Emerson, and the factory tells him to report to work the next morning.
The episode of Bledsoe’s letters fundamentally changes the way the narrator thinks about the world. The man who he aspired to emulate has deeply and cynically betrayed him. He now understands that he will be given nothing easily, and decides to harness his anger to take his next steps.