It is made clear that Soapy is homeless, one of the underclass men and women who flocked to New York City during the earliest years of the twentieth century.
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.
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.
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.
As Soapy listens to the church organ play an anthem, he experiences a spiritual epiphany in which he resolves to cease to be homeless, end his life as a tramp afflicted with unemployment, and regain his self-respect.
In February 1909, less than five years after the story's initial publication, O. Henry's work was adapted to the film Trying to Get Arrested, which was directed by D. W. Griffith, produced by the Biograph Company of New York, and released on April 5, 1909.