O. Henry himself had served three years in a state penitentiary for embezzlement, and he had never gotten over the experience. He wrote under a pseudonym because he was trying to hide from his past. He lived in constant fear that his past would be exposed. He became an extreme alcoholic and died of cirrhosis of the liver and other ailments associated with alcoholism at the age of forty-seven. Since he never got over the shame and the stigma of having been a convict, some of his short stories, such as "A Retrieved Reformation" and "The Cop and the Anthem," deal with the truth that it is difficult for a man to get accepted back into polite society once he has lost his place.
Soapy was once a respectable gentleman and still tries to preserve that appearance even though he has become a bum. The other bums, who have never known anything better, treat him with respect because his manners and diction show he comes from a better social class. O. Henry refers to one of the Madison Square Garden benches as "his bench" several times throughout the story. Soapy has claimed one of the benches as his private home, and the other homeless men defer to him. But when Soapy is inspired to change his ways and become a respectable citizen again, he finds it is impossible. He is permanently outside looking in, just as he is outside the church looking in when the cop arrests him for vagrancy and loitering.
Soapy has lost his place forever. He has waited too long to try to reform. He is only kidding himself when he thinks he can turn the clock back. He may feel like a gentleman, but society has branded him as a bum.
Something similar happens to George Hurstwood in Theodore Dreiser's novel Sister Carrie, and something similar also happens to William Dorrit in Charles Dicken's novel Little Dorrit. Dorrit has been confined to Marshalsea debtors prison for twenty years and then miraculously becomes a rich man as the only heir to a large estate. But he is too old to change his thinking. He continues to feel like an imprisoned pauper no matter how hard he tries to play the role of an upper-class gentleman.
Another work dealing with a similar theme is Eugene O'Neill's play The Iceman Cometh. The e-notes Summary of O'Neill's play states:
The residents of the boardinghouse are all failures; all were onetime viable members of society, but all have been kept from having to face their degeneration by the illusion that he or she will or at least could make up for that failure and become a success. They help sustain one another by professing mutual belief in one another’s pipe dreams.
And yet another literary work reflecting a similar theme is John Steinbeck's novelette Of Mice and Men.
In Nathaniel Hawthorne's excellent story "Wakefield," the author closes with these words:
Amid the seeming confusion of our mysterious world, individuals are so nicely adjusted to a system, and systems to one another, and to a whole, that, by stepping aside for a moment, a man exposes himself to a fearful risk of losing his place forever. Like Wakefield, he may become, as it were, the Outcast of the Universe.