The short story's narrative is set in an unstated day in late fall. Soapy faces the urgent necessity of finding some sort of shelter for the winter. He is psychologically experienced in thinking of Blackwell's Island, the local jail, as a de facto winter 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.
O. Henry's short stories are well known for their wit, wordplay, warm characterization and clever twist endings.