A number of O. Henry's stories are based on several interrelated morals. These are:
- Crime does not pay.
- Honesty is the best policy.
- It is difficult for criminals to reform.
Jimmy Valentine decides to go straight because he falls in love with a beautiful girl and wants to be worthy of her. But his past catches up with him in the form of Ben Price, apparently an insurance detective. Jimmy would have gone to prison for a long stretch and would have lost the girl he was engaged to marry if Ben Price hadn't decided to let him go because of his heroic sacrifice in saving the little girl in the bank vault from certain death. Price was a wise man and understood that Jimmy was no longer a threat to society because he had a successful business, had become a pillar of the community, and was about to be married. Jimmy's reformation is explained in the letter he is sending to the man to whom he is giving his deluxe burglar tools.
And, also, I want to make you a present of my kit of tools. I know you'll be glad to get them—you couldn't duplicate the lot for a thousand dollars. Say, Billy, I've quit the old business—a year ago. I've got a nice store. I'm making an honest living, and I'm going to marry the finest girl on earth two weeks from now. It's the only life, Billy—the straight one. I wouldn't touch a dollar of another man's money now for a million. After I get married I'm going to sell out and go West, where there won't be so much danger of having old scores brought up against me.
"Crime does not pay" and "Honesty is the best policy" are two sides of the same coin. In O. Henry's "Twenty Years After" we see that 'Silky' Bob has been a criminal for twenty years and has little to show for it except a diamond scarf pin which identifies him to the New York police as the man wanted in Chicago. He is always on the run from people he has swindled or from the law. He has many enemies but only one friend--and that one friend, Jimmy Wells, has become a cop who turns him in. In "The Ransom of Red Chief" the two would-be kidnappers have been committing crimes for years and have nothing but six hundred dollars between them. They have to sleep on the ground and cook over a campfire. Their kidnap victim turns out to be such a hellcat that they have to pay his father to take him off their hands. In "The Cop and the Anthem" "Soapy" decides to reform and become a respectable citizen again, but his fate illustrates the moral that it is difficult to reform. "Soapy" has been on the skids for so long that he can't get off.
O. Henry spent several years in a state prison for embezzlement. He met many criminals and continued to associate with them after his release. One of his friends was Al Jennings, a notorious train robber. O. Henry came to the conclusion that crime does not pay. Fortunately, he had a great talent for writing which enabled him to make an honest living. But his past haunted him for the rest of his life. He was always afraid of being exposed as a convicted felon. He wrote under an assumed name. He became a very heavy drinker and died of alcoholism while only in his forties.