The theme of O. Henry's "A Retrieved Reformation" can be stated in either of two old adages. One is "Crime does not pay." The other is "Honesty is the best policy." O. Henry served several years in a state prison for embezzlement. He met a lot of career criminals and saw that in one way or another their choice of a life of crime was a foolish mistake. In O. Henry's story "After Twenty Years" his character 'Silky' Bob seems superficially successful, but he has been on the run all his life. He has never had a home or family, and his only friend in the world, Jimmy Wells, has him arrested and turned over to the Chicago police. Jimmy Wells, on the other hand, has led an honest life and seems like a happy man, content with his job as a policeman. In "A Retrieved Reformation" Jimmy Valentine spells out O. Henry's theme in a letter he writes to a friend in which he tells him:
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.
O. Henry uses the character of Jimmy Valentine to illustrate the truth he learned the hard way: that the qualities that make a successful criminal can also make a successful honest man and that the life of an honest man is better in every respect. Jimmy's reformation is threatened when he is exposed as a professional safecracker in the bank where he saves the little girl locked in the vault. However, Ben Price sees this as proof that Jimmy has really become a man of integrity. The story ends with one of O. Henry's trademark surprises.
“Hello, Ben!” said Jimmy, still with his strange smile. “Got around at last, have you? Well, let's go. I don't know that it makes much difference, now.”
And then Ben Price acted rather strangely.
“Guess you're mistaken, Mr. Spencer,” he said. “Don't believe I recognize you. Your buggy's waiting for you, ain't it?”
Jimmy's "strange smile" is probably ironic. He is thinking that once you have taken the wrong path in life there is no turning back. But the story proves that it is never too late to reform.