The short story's narrative is set in an unstated day in late fall. Because the city trees' deciduousleaves are falling and there is a hint of frost in the air, Soapy faces the urgent necessity of finding some sort of shelter for the winter. He is psychologically experienced in thinking of the local jail as ade facto homeless shelter, and the narrative shows him developing a series of tactics intended to encourage the police to classify him as a criminal and arrest him.
Soapy's ploys include swindling a restaurant into serving him an expensive meal, vandalizing the plate-glass window of a luxury shop, repeating his eatery exploit at a humble diner, sexually harassing a young woman, pretending to be publicly intoxicated, and stealing another man's umbrella.
However, all of these attempts are quickly exposed as failures. The upper-class restaurant looks at Soapy's threadbare clothes and refuses to serve him. A police officer responds to the broken window but decides to pursue an innocent bystander. The diner refuses to have Soapy arrested, and instead has two servers throw Soapy out onto a concrete pavement.
Soapy's failures to earn his desired arrest continue. The young woman, far from feeling harassed, proves to be more than ready for action. Another police officer observes Soapy impersonating a drunk and disorderly man, but assumes that the exhibitionistic conduct is that of a Yale student celebrating a victory over "Hartford College" in football. Finally, the victim of the umbrella theft relinquishes the item without a struggle.
Based on these events, Soapy despairs of his goal of getting arrested and imprisoned. With the autumn sun gone and night