It would seem that the first important change in Jimmy Valentine occurred instantaneously when he fell in love at first sight with a small-town girl named Annabel Adams.
A young lady crossed the street, passed him at the corner and entered a door over which was the sign “The Elmore Bank.” Jimmy Valentine looked into her eyes, forgot what he was, and became another man.
Jimmy had learned something about repairing shoes while he was serving ten months in prison for burglary. He had moved to Elmore, Arkansas because he was getting too notorious in his previous area of operations around Indiana. He had opened a shoe business purely as a "front" but planned to continue his profession as a safecracker--until he fell in love. After that he decided to go straight. He wanted to be worthy of this lovely girl, and he knew that she would despise him if she found out he was a criminal with a prison record. So he changed his name to Ralph Spencer and became a legitimate businessman.
That was the second way Jimmy changed. As a result of learning to care for Annabel, Jimmy began to realize that not only is life better if you are honest, but life is better if you think about other people rather than only about yourself. He demonstrated this third change when he sacrificed all the benefits of his "reformation" in order to save a little girl who had gotten accidentally locked in a bank vault. In doing so, he had to open his suitcase and reveal that it was full of safecracking equipment, thereby revealing his true identity. Meanwhile Ben Price was waiting to arrest him for the three bank jobs he had pulled after being pardoned and released from prison. It seemed as if he had lost everything, including the girl he loved.
But Ben Price understood that Jimmy had changed completely. There was no need to send him to prison. Prison was intended to reform people, and Jimmy was already reformed. Jimmy had learned many things in a short time, including the fact that a man who has the talents to become a successful criminal can use the same talents to be come successful in the world of honest men and women. In a letter to a friend, Jimmy had written:
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.
When Jimmy approached the bank detective, expecting to be arrested, Ben Price told him:
“Guess you're mistaken, Mr. Spencer,” he said. “Don't believe I recognize you. Your buggy's waiting for you, ain't it?”
Jimmy had enjoyed prosperity as a professional safecracker, but there were many drawbacks which he came to realize after he went straight. He had always been on the lam, always looking over his shoulder. He was getting to be too well known, so that it was easier to get sent to prison and harder to get out. He was in danger of compiling such a long criminal record that he would always be getting pulled in on suspicion when a bank job occurred. And he was in danger of becoming a hardened con with the mentality of an incorrigible recidivist. O. Henry had met many such men when he was serving three years in state prison for embezzlement. The moral of O. Henry's story can be expressed in two old adages, either: "Crime does not pay," or "Honesty is the best policy."