O.Henry's stories always have a moral undercurrent that is often hidden beneath layers of irony. In this short story the central character, Soapy, is a homeless man with a need for winter shelter and a clever way to get it. Unfortunately, Soapy is unable to get himself arrested no matter how hard he tries. Finally, Soapy stops outside a church and lets his mind wander to happier times and he determines to better his place in life. At that moment, he is arrested for loitering and sent to jail for the winter.
On the surface the story seems to illustrate the cliche, "If it wasn't for bad luck I'd have no luck at all." Upon deeper examination, however, there is a deeper and more relevant meaning. O.Henry had an eye for the details of unfortunate people. Early in the story O.Henry tells that Soapy is shaved, clean, and as well dressed as can be for a vagrant. This is the first indication that there is more to Soapy than a stereotypical "bum." Later O.Henry makes the point that at one time in Soapy's life there were "such things as mothers and roses and ambitions and friends and immaculate thoughts and collars."
In providing these details, O.Henry's moral message comes to life. Every person has a story. Even the homeless man on the street has a history that doesn't include his current state of affairs. Even though we don't know how or why Soapy became homeless, O.Henry teaches the reader to feel sympathy for him and to hope for better things when Soapy begins to plan a future for himself. The irony leaves the reader disappointed--but perhaps a bit more compassionate to those who may not have crossed consciousness before.