There is only one character given a name in the story; Soapy is the protagonist, a man with no last name who is homeless, having come to New York to find his fortune at the beginning of the twentieth century. It is late fall, and it's getting cold and frosty. Soapy is worried because he has nowhere to sleep and knows he needs to make some kind of plan for himself if he is to survive the winter. He tends to think of the jail, Blackwell's Island, as his bad-weather hostel and he starts to commit petty crimes with the objective of getting arrested and taken to Blackwell's Island where he will be warm and receive three square meals a day. He plans to throw a brick through a store window, he creates an elaborate and expensive dine and dash, and he pretends that he is drunk and disorderly, but the police don't pick him up because his plan does not work. The expensive restaurant don't let him in. The store owner thinks that another innocent bystander has broken the window. Nothing he tries works.
Soapy comes to terms with the fact that his ploys to get arrested are not going to work. He hovers outside a church, trying to decide what to do next, and whilst he lingers he listens to a church organ playing a hymn. He begins to have a personal epiphany and decides to stop being homeless and jobless, and to get his self-respect back. He was offered a job once; he resolves that the next day he will seek out the man who offered it, and ask if the offer still stands.
While Soapy is daydreaming, a policeman taps him on the shoulder and asks what he is doing. He is arrested for loitering and the following day sentenced to three months in Blackwell's Island for this misdemeanor.