Wilhelm and Tamkin go to lunch in a crowded cafeteria, where Tamkin talks at length. He gives Wilhelm advice about what to do with the money he will inherit from his father, while Wilhelm says that he loves his father and does not want him to die. Tamkin talks about his own father, telling another fantastic story that Wilhelm does not really believe. He thinks about his own sons, about how he appears to them and how they think of him. He recalls the times when he takes them to baseball games. He thinks they do not know how much he cares for them, and he blames Margaret for turning them against him. He also thinks of Olive, the woman he loves and would marry if Margaret were to relent and give him a divorce.
Tamkin interrupts his thoughts, saying that Wilhelms father is jealous of Wilhelm because he left his wife. He also says that Wilhelms wife envies him too, because he is free and is now able to see young women. Tamkin tells of his own wife. She was an alcoholic, but he loved her. She drowned in Cape Cod, and it might have been a suicide. He says he tried to cure her, because he is a healer. Wilhelm does not believe his story, and thinks contemptuously of him. He realizes that the man is a charlatan but he has to go along with him because of their joint investments.
Tamkin tells him a story about Mr. Rappaport, that he had two wives and maintained two families in two separate homes for many years. Wilhelm thinks this is just another of Tamkins stories. Tamkin explains that he tells the story to show that some men are able to free themselves from the guilt feelings that women try to inflict on them. Wilhelm complains again about his family situation, but Tamkin asks him why he allows his wife to make him suffer so much. He tells her not to play her game, not to “marry suffering,” as so many people do. Wilhelm has to admit that Tamkin, in spite of all his falsehoods, is right about this.
They go back to the market. As they approach the building they see Mr. Rappaport, who asks Wilhelm to help him across the road. Wilhelm does not want to, but he does. Mr. Rappaport tells him a story of how he fought in the Spanish-American war. He was on the beach shortly after the battle of San Juan Hill, and encountered Teddy Roosevelt there. Roosevelt yelled at him to get off the beach since he had no orders to be there. Rappaport is very proud of this memory.
At the market, Wilhelm discovers that lard has dropped twenty points since noon. Rye has fallen too, and so he and Tamkin have lost their chance to sell while the going was good. Wilhelm looks around for Tamkin, but he is nowhere to be seen. Wilhelm is in a panic, since he is wiped out financially. He feels like crying but tries to stay calm. He looks for Tamkin in the mens toilet, without success. He still hopes that at least he will get back from Tamkin the two hundred dollars he is owed from the original deposit.
Once again Tamkin reveals that although he may be untrustworthy and frequently tells fantastic, unbelievable stories, he also has genuine insight into the truth. The advice he gives to Wilhelm about Margaret is essentially the same as that given by Wilhelms father in Chapter III. Wilhelm suffers because he allows Margaret to inflict suffering on him. But Wilhelm accepts this reproach from Tamkin, whereas he had fought against it when his father had pointed it out. Deep down he knows that Tamkin is right. The rest of the chapter confirms that Wilhelm is somehow “married” to suffering. He finds that he has lost all his money and allowed himself to be cheated by Tamkin. This is just the latest episode in a long series of bad decisions stretching back to when he gave up college to try to become an actor in Hollywood. He always manages to sabotage himself. At the end of the chapter he is “like a man about to drown.” This is another occurrence of the metaphor of drowning that pervades the novel (see Metaphor section of this guide).