How was Soapy planning to cope with winter?  

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Soapy has obviously had years of experience surviving as a homeless man in New York. He sleeps on a park bench which, because of his seniority and dignity, is considered reserved for him by the other homeless men who sleep in Washington Square. But Soapy cannot sleep outdoors in the winter. The temperature at night can fall below zero, and many homeless people freeze to death in the New York winters. Soapy intends to do what he has done regularly in winters past. He will get himself arrested and sentenced to three months in jail on Riker's Island. 

The hibernatorial ambitions of Soapy were not of the highest. In them there were no considerations of Mediterranean cruises, of soporific Southern skies drifting in the Vesuvian Bay. Three months on the Island was what his soul craved. Three months of assured board and bed and congenial company, safe from Boreas and bluecoats, seemed to Soapy the essence of things desirable.

O. Henry treats Soapy's situation with characteristic humor. This way of dealing with a serious or even tragic subject in a humorous fashion was originated by Charles Dickens, who had started his literary career as a humorist with his Pickwick Papers. O. Henry was undoubtedly inspired by the great Charles Dickens, whose humorous treatment of the plight of Ebeneezer Scrooge in A Christmas Carol is an excellent example of Dickens' style. The humor seems to have the intended effect of assuring readers that the problem may be extremely serious but that things will come out all right in the end.

Soapy's situation is very serious. As O. Henry illustrates it in graphic terms:

On the previous night three Sabbath newspapers, distributed beneath his coat, about his ankles and over his lap, had failed to repulse the cold as he slept on his bench near the spurting fountain in the ancient square. So the Island loomed big and timely in Soapy's mind. 

Abandoned newspapers are plentiful and cost nothing. They make excellent insulation, and many homeless men will pack multiple pages under their vests and coats, under their sleeves, down the back of their trousers and all along their trouser-legs for protection during the night. If they sleep outdoors they will use more newspapers in place of blankets. But even with three big Sunday editions of the newspaper insulating and blanketing him, Soapy still feels the bite of winter. He has a life-or-death problem to solve--but O. Henry makes it seem funny and makes Soapy himself seem funny.

O. Henry creates characters to fit his stories. Soapy is a bum, but he is obviously descended from a higher station in life. He has middle-class tastes, middle-class dignity, and a middle-class vocabulary. He tries very hard to get arrested for vandalism, disorderly conduct, petty theft, vagrancy, loitering, and every misdemeanor he can think of. His uncanny failure to get arrested for the first time in many winters, along with the favorite old church anthem he happens to hear during his wanderings about Manhattan, create an epiphany.

An instantaneous and strong impulse moved him to battle with his desperate fate. He would pull himself out of the mire; he would make a man of himself again; he would conquer the evil that had taken possession of him. There was time; he was comparatively young yet; he would resurrect his old eager ambitions and pursue them without faltering. Those solemn but sweet organ notes had set up a revolution in him. 

But, ironically, it is just at this moment that a uniformed cop finally takes some notice of him. Soapy is led away to jail, and the next morning he is sentenced to three months on Riker's Island--just what he had wanted in the first place. The moral of O. Henry's story might be derived from the moral Nathaniel Hawthorne invented for his excellent story "Wakefield."

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.

 

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