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Soapy's name suggests he is not a bad character, but he is looking for an easy way to spend the winter. Rather than getting a job to earn money, his goal at the beginning of the story is to commit a minor crime that will guarantee him "three months on the Island," in jail. He'll have food and a warm place to stay. Soapy is too proud to accept public charity; he doesn't want to accept anything that will have some kind of strings attached. He's clever to try six different ways to get arrested, but it seems he is incredibly unlucky because every attempt fails, usually in some ironic sense.
When he finally hears the organ music, decides to turn over a new leaf, and get a job, he is ironically arrested, of course, when he doesn't want to be, and his original wish is granted. We'd have to label him proud, persistent, lazy, clever, and unlucky. O'Henry's characters often experience the kind of surprise ending Soapy does.
Soapy is an unusual type of bum. He might be called a "gentleman-bum." At one time he was a member of the middle class. He still retains the speech and manners of a gentleman, and he does his best to keep up appearances. Something must have happened to him to make him give up on life and decide to abscond from respectable society and a conventional lifestyle. It could have been a divorce or a business failure or something else. We get an impression of his lingering middle-class manners in several of the little episodes in which he tries to get arrested. Here is one example:
At a table he sat and consumed beefsteak, flapjacks, doughnuts and pie. And then to the waiter he betrayed the fact that the minutest coin and himself were strangers.
“Now, get busy and call a cop,” said Soapy. “And don't keep a gentleman waiting.”
The meal he planned to order at the first restaurant, from which he was ejected before he had a chance to sit down, shows that he was used to an privileged lifestyle.
A roasted mallard duck, thought Soapy, would be about the thing—with a bottle of Chablis, and then Camembert, a demitasse and a cigar. One dollar for the cigar would be enough.
If Soapy were an ordinary bum with no education and no past history of respectability and affluence, his epiphany and attempted transition at the end, when he hears the church anthem, would not be as effective. When Soapy decides to get a job and reform, we really believe he can and will do it. Soapy was a forerunner of the many affluent men who lost everything in the great Wall Street crash of 1929 and found themselves standing in breadlines. Soapy also resembles George Hurstwood in Theodore Dreiser's novel Sister Carrie (1900), a man who had a good, soft job, a big house, a family, membership in exclusive men's clubs, and all the other symbols of success. Hurstwood lost his nerve after committing the bad mistake of stealing money from his employers in order to run off with the much younger Carrie Meeber, and he rapidly descended into the lower depths, begging for nickels and dimes on the New York streets, and finally committing suicide in a flophouse. What happens to Soapy is similar to what happened to Hurstwood: he found out that it is easy to go downhill in life but very hard to climb back up. Soapy is proud and fearless. He still thinks of himself as a gentleman, but society thinks of him as a bum.
Soapy is a poor, lazy and homeless person.Actually he is not a bad guy but he wants to spend his winter in the Blackwell's Island where he can easily get food,shelter and clothes for three months.So he tries to commit minor crimes just to get arrested and spend winter in the prison.
In reference to your line, "Soapy's name suggests he is not a bad character": I never viewed it that way and I am not sure that it should be. My take is that it was intended to simply be ironic a homeless man with a name Soapy referring to cleanliness.
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