Throughout "A Retrieved Reformation" O. Henry takes pains to show that, although Jimmy Valentine is a criminal, he is also a good-looking, intelligent, enterprising man with good taste in clothes, good manners, and possessing an engaging personality. Even in the first sentence, O. Henry writes that:
A guard came to the prison shoe-shop, where Jimmy Valentine was assiduously stitching uppers.
Jimmy does not have to be working so "assiduously." There is no one watching him. However, that is part of his character. He works hard at everything he does. He is so intelligent that he has learned a lot about the shoe trade during the short time he has been in prison. O. Henry's purpose in making Jimmy such an exceptional character was to highlight the theme that a person who can be a successful crook can be equally successful as an honest citizen. Even the warden likes Jimmy. He jokes with him and tells him,
Brace up, and make a man of yourself. You're not a bad fellow at heart.
Everybody likes Jimmy. The narrator says of him:
When a man with as many friends on the outside as Jimmy Valentine had is received in the "stir" it is hardly worth while to cut his hair.
Jimmy had been sentenced to four years in prison for a "job" he did in Springfield. He only served ten months because he had so many friends on the outside.
When Jimmy falls in love at first sight with Abigail Adams in Elmore, Arkansas, she is also smitten with him.
Jimmy Valentine looked into her eyes, forgot what he was, and became another man. She lowered her eyes and coloured slightly. Young men of Jimmy's style and looks were scarce in Elmore.
It is because of Jimmy's many attractive qualities that—though a stranger in a small town—he is able to ingratiate himself with Abigail and her family so quickly. It is also because of these qualities, along with his brains and industry, that he is able to become a successful businessman in a short time. It only takes the love of a good woman to make him change overnight into an honest citizen.
Mr. Ralph Spencer, the phoenix that arose from Jimmy Valentine's ashes—ashes left by the flame of a sudden and alterative attack of love—remained in Elmore, and prospered. He opened a shoe-store and secured a good run of trade.
Even Ben Price, the detective, likes Jimmy. Ben probably likes him even more when he sees what a noble sacrifice the erstwhile safecracker is making in order to save the life of the little girl who accidentally became locked inside the supposedly burglar-proof bank vault. The reader is led to like Jimmy, too, and does not want to see him lose his fiancee, business, and reformation by being carted off to prison. We know that, as the warden told him, he is not a bad fellow at heart. We are delighted with O. Henry's surprise ending when Ben Price decides not to do what the reader expects him to do.
"Guess you're mistaken, Mr. Spencer," he said. "Don't believe I recognize you. Your buggy's waiting for you, ain't it?"