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As winter approaches, Soapy, a homeless man living in New York City, realizes he needs shelter for the cold months ahead. He has been sleeping on a bench in Madison Square Park, but knows this won't be sustainable during winter. Rather than seeking employment or other conventional solutions, Soapy decides his best option is to get arrested and spend three months in Blackwell's Island prison, which would provide him with food, shelter, and warmth.

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November: Soapy's First Attempt - The Restaurant

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November: Soapy's First Attempt - The Restaurant

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Soapy enters an upscale restaurant pretending to be a wealthy customer. His plan is to order and eat an expensive meal, then reveal he cannot pay for it, resulting in his arrest. However, before he can execute his plan, the restaurant staff notices his shabby appearance and unkempt clothing. The headwaiter and two other staff members quietly but firmly escort him out of the establishment before he can even order, foiling his first attempt to get arrested.

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Same Day: Soapy's Second Attempt - Breaking a Window

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Same Day: Soapy's Second Attempt - Breaking a Window

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After being ejected from the restaurant, Soapy picks up a cobblestone and throws it through the window of a nearby shop. His plan is to be caught for vandalism and property damage. He waits at the scene for the police to arrive and arrest him. A crowd gathers around the broken window, and a policeman rushes over. However, when Soapy claims responsibility for breaking the window, the officer doesn't believe him and instead pursues a man running away from the scene.

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Later That Day: Soapy's Third Attempt - The Restaurant Again

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Later That Day: Soapy's Third Attempt - The Restaurant Again

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Soapy tries another restaurant, this time one with more moderate prices where his appearance might not immediately give him away. He eats a hearty meal, then tells the waiter he cannot pay. However, instead of calling the police as Soapy expected, the restaurant staff simply throws him out onto the street, without involving law enforcement. Soapy remains free but increasingly frustrated by his failed attempts.

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Evening: Soapy's Fourth Attempt - Harassing a Woman

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Evening: Soapy's Fourth Attempt - Harassing a Woman

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Growing desperate, Soapy notices a young woman standing alone at a street corner. He approaches her and acts in an inappropriate and offensive manner, hoping to be arrested for harassment. However, the woman turns out to be a prostitute who is pleased by his attention. When a police officer approaches, Soapy quickly leaves the scene to avoid any misunderstanding that might lead to complications rather than his desired imprisonment.

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Night: Soapy's Fifth Attempt - Disorderly Conduct

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Night: Soapy's Fifth Attempt - Disorderly Conduct

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Soapy decides to create a public disturbance by shouting and singing loudly in the street. He makes as much noise as possible, expecting to be arrested for disorderly conduct. A nearby police officer observes Soapy's behavior but misinterprets it, believing that Soapy is a college student celebrating after a football game. The officer simply tells him to quiet down, and Soapy's fifth attempt also fails.

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Late Night: Soapy's Sixth Attempt - Stealing an Umbrella

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Late Night: Soapy's Sixth Attempt - Stealing an Umbrella

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Soapy spots a man looking at items in a store window who has placed his umbrella against the wall. Soapy steals the umbrella in plain sight, hoping to be caught for theft. When the man notices, he confronts Soapy, but instead of calling for police, the man becomes apologetic, claiming he had mistakenly taken someone else's umbrella the day before and that the one Soapy took might not actually belong to him. This confusion allows Soapy to walk away, still free.

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Walking dejectedly after his many failed attempts, Soapy passes by a church. He hears the organ music coming from inside, which triggers memories of his past life. The music reminds him of his mother, his childhood home, and the respectable man he once was. In this moment of reflection, Soapy experiences an epiphany and decides to turn his life around, resolving to find work and become a better person.

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Just as Soapy makes his decision to reform his life, a police officer approaches him. The officer notices Soapy loitering near the church and asks what he's doing. When Soapy explains he was just listening to the music, the officer doesn't believe him and arrests him for loafing. In the ultimate irony, Soapy is sentenced to three months on Blackwell's Island—achieving his original goal precisely at the moment he had decided to abandon it.