Theory:

     Soapy’s hopes for the winter were not very high. He was not thinking of sailing away on a ship. He was not thinking of southern skies, or of the Bay of Naples. Three months in the prison on Blackwell’s Island was what he wanted. Three months of food every day and a bed every night, three months safe from the cold north wind and safe from cops. This is what Soapy wanted most in the world.
 
     For years, Blackwell’s Island had been his winter home. Richer New Yorkers made their plans to go to Florida or to the shore of the Mediterranean Sea each winter. Soapy made his small plans for going to the Island.
Explanation:
 
Soapy only had a few hopes in his mind, and his expectations were low for winter. On the other hand, the New York people plan to visit the warmer places during the winter season. But Soapy was quite different, and he knew he couldn't expect anything more. He was not thinking of sailing away on a ship, visiting the warmer places, or even travelling to the Bay of Naples during the winter season. All he wanted was three months of stay in prison.
 
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Soapy was not thinking about sailing away on a ship or visiting the Bay of Naples (left to right)

The winter season would remain for almost three months. Hence, he preferred to stay in prison for three months until the winter gets over. The best thing Soapy wanted in his life was three months of stay in prison, food for every day and three months of protection from the bitter north wind and police officers.
 
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Soapy wants three months of prison on Blackwell's Island

The rich people of New York City had numerous plans for the winter season. They made their plans to visit Florida or the shore of the Mediterranean Sea. Soapy, on the other hand, had his plan to go to prison. The lives of wealthy New Yorkers and Soapy's are compared here to indicate that the rich people wanted to enjoy the gorgeous location while Soapy's goal was to reach the prison. During the winter season, Blackwell's Island was his pleasant home. So, while the rest of the New Yorkers were preparing for their winter vacations, Soapy was making plans to return to the jail.
 
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New Yorkers made their plans to visit Florida or the shore of the Mediterranean Sea* (left to right)
 
Meanings of the difficult words:
 
S.No
Words 
Meanings
1
Island A piece of land surrounded by water
2
Prison A building where criminals are forced to live as a punishment
3
CopA police officer
4
Florida A state in the southeastern United States between the Atlantic and the Gulf of Mexico
5
Southern skiesRegions with warm sunlight
6
Blackwell’s Island Name of a prison
Reference:
National Council of Educational Research and Training (2007). An Alien Hand. The Cop and the Anthem- O. Henry(20-29). Published at the Publication Division by the Secretary, National Council of Educational Research and Training, Sri Aurobindo Marg, New Delhi.