On his bench in Madison Square, Soapy begins to feel the chilling effects of winter and decides he must leave his bench. His “hibernatorial ambitions” are modest, in contrast to those of wealthier New Yorkers who escape the winter via Mediterranean cruises. Soapy only wants three months of guaranteed room and board on “the island”—Blackwell’s Island, where he has spent the past three winters just as other New Yorkers head to the Riviera or Palm Springs.
O. Henry’s dark sense of irony is on display from the very beginning of the story, as Soapy’s annual migration is treated as a natural occurrence (a “hibernatorial” pursuit) that is similar to the southern migration of geese. Soapy shares a kinship with his fellow New Yorkers, but the bitterly ironic fact is that he is headed to a much different island than his wealthy counterparts.
The newspapers under his coat no longer keep Soapy warm, but he resents the enforced humility of many of the citizens charitable institutions. He’d rather be “a guest of the law, which […] does not meddle unduly with a gentleman's private affairs.”
Soapy remains a proud, dignified character who wants to preserve his independence despite his poverty. The comedic irony is that he plans to do so by going to jail.
Soapy thus resolves to get himself arrested in order to obtain lodging at Blackwell’s Island for the winter. His first attempt occurs at a glittering café on Broadway, where he is confident he can scam a meal for himself because he is clean-shaven, his coat is decent, and he is wearing a tie. He imagines the decadent meal that awaits him: roasted mallard duck […] with a bottle of Chablis, and then Camembert, a demi-tasse and a cigar. One dollar for the cigar would be enough,” he reasons. However, before he can even make it to a table, a waiter spots Soapy’s frayed trousers. Instead of calling the police, the staff throws Soapy out on the street.
Soapy is a character with refined, expensive tastes, which suggests he was not always poor—and also that the poor are not so different from the wealthy, despite stereotypes of them as uncultured and uncouth. Despite his confidence in his ability to move fluidly through different layers of society because he knows how to dress and act the part, the reality of Soapy’s social status is embodied in his frayed trousers, which give him away.
At a shop window lit up brightly with “cunningly displayed wares,” Soapy hurls a cobblestone through the glass and shatters it. When a police officer arrives at the scene of the crime, Soapy identifies himself as the culprit and peppers in a few sarcastic, overly-friendly quips, but the officer’s “mind” refuses to accept Soapy “even as a clue.” Rather than arrest the perpetrator of the crime, the cop runs off to chase another man.
The comic, over-the-top quality of Soapy’s crime and admission hint at his mounting desperation and raise the story’s stakes. No matter how confidently he pursues arrest and how visually obvious his crime might be, all that matters is the police officer’s perception of Soapy, suggesting that a man is only homeless if a person in a position of power above him thinks of him that way.
Despite thinking himself above it and considering the role despicable and execrated, Soapy decides to assume the role of a “masher,” a man who harasses women on the street. Tilting his hat at a “killing cant” and flirting impudently with a woman he finds window-shopping, Soapy’s plan backfires: he has failed to identify the woman as a prostitute, and she is in fact intrigued by his advances. The woman herself likewise misidentifies Soapy as a paying customer, embroiling the two characters in a sadly comic exchange that neither one can fulfill.
Soapy envisions himself as a gentleman and considers this role beneath him. Much in the same way that he was misidentified by a cop, Soapy misidentifies a character when he thinks he is above the role he must play. The stark irony, however, is that Soapy must engage in the behaviors of a “masher” in order to achieve his goal, thus making him into a masher himself in the process.
Panicking at the thought that “some dreadful enchantment” might have rendered him immune to arrest, Soapy attempts to engage in disorderly conduct and get arrested by shouting drunken gibberish at a police officer. He dances, howls, raves, and even goes so far as to “disturb the welkin.” However, the police officer, who speaks in a jargon-heavy form of broken English, misidentifies Soapy as a Yale student celebrating a recent football victory over Hartford College and ignores him, noting that he has instructions to “lave them be.”
There is a sense throughout the story that Soapy is doomed or cursed, suggesting that nothing he does can change the vicious cycle of homelessness in which he is trapped. Shouting obscenities at a cop causes a wildly outsize response: the cop perceives him as an ivy league student at a prestigious university, which further suggests that Soapy’s fate is not in his own hands.
As his desperation deepens and his actions become increasingly flighty and desperate, Soapy somewhat resignedly enters a cigar store, where he approaches a well-dressed man lighting a cigar and steals his silk umbrella, almost arrogantly self-assured that this action will get him arrested. When a police officer witnesses the dispute, the man with the umbrella stutters and retreats, revealing to Soapy that he has once again misidentified this man as a wealthy member of a society when he is in fact an umbrella thief himself.
It is only once Soapy performs his crime that he sees this fellow criminal for who he is, shattering his confidence in his ability to identity individuals based upon his perception of their appearances and the material objects surrounding them. This once again reveals to Soapy that he commits the same errors of perception as the people he encounters throughout the story.
Dejected and discouraged, Soapy arrives at an iron fence surrounding an old church. The tone of the story shifts deliberately in this scene, creating a “lustrous and serene” atmosphere that is almost pastoral. From inside the church, Soapy hears an organist playing an anthem. The song is so moving to Soapy that he resolves to reform himself, get a job, and become a contributing member of society. He will pull himself out of the mire, he tells himself, because the organ notes have “set up a revolution in him.” He will head into the roaring downtown district and find work, he tells himself. However, before he can put his plan into action, Soapy feels the familiar hand of a police officer on his arm, he is arrested for loitering, and he is sentenced to three months on Blackwell’s Island the next morning.
O. Henry shifts deliberately from a jaunty, fast-paced tone to an earnest, slowed-down one in order to set up one of his infamous twist endings, but also to provide commentary. Rather than end the story on an uplifting note, in which a homeless man is so inspired by an “anthem” that he resolves to pull himself up by his bootstraps and chase the American Dream, the story screeches to a halt with a series of rapid-fire exchanges that reward Soapy with the thing that has eluded him the entire story, but which is ironically the thing he no longer desires. This provides tragic irony and social commentary in tandem, as readers once again see that Soapy is powerless to escape from his homelessness and the way he is perceived by the world.