Jimmy Valentine may have been toying with the idea of going straight before he saw Annabel Adams in Elmore, Arkansas and fell in love. O. Henry plants several such suggestions.
He had served nearly ten months of a four year sentence. He had expected to stay only about three months, at the longest.
This experience must have made him realize that he was getting to be too notorious as a master safecracker. It is becoming harder for his friends to "spring" him. And it could get worse. As Ben Price observes later in the story:
Yes, I guess I want Mr. Valentine. He'll do his bit next time without any short-time or clemency foolishness.”
Jimmy has probably been thinking the same thing. He got a four-year sentence for the Springfield job, but he might get an even longer sentence the next time he gets caught. The fact that he has a record would be prejudicial against him.
Jimmy has been working in the prison shoe shop and seems to have been enjoying it. After all, he is a craftsman, and this is just another kind of craftsmanship. This experience may have given him the notion of opening a shoe business--but he might have been thinking of just using the legitimate business as a "front."
When he tells the warden he knows nothing about safecracking and has never been in Springfield in his life, the warden just laughs. Mike Dolan just laughs when Jimmy claims he is now working for the New York Amalgamated Short Snap Biscuit Cracker and Frazzled Wheat Company. Everybody knows about Jimmy Valentine in spite of the fact that he has tried very hard to keep a low profile.
Long jumps, quick get-aways, no confederates, and a taste for good society—these ways had helped Mr. Valentine to become noted as a successful dodger of retribution.
So when Jimmy falls in love at first sight, he is already psychologically prepared to change his identity and reform. He is able to do so because he is gifted with a superior intelligence and a winning personality. He can be just as successful as a businessman as he can as a safecracker. He tells an old friend in a letter:
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.
This is the moral of the story. Honesty is the best policy. Crime does not pay. O. Henry illustrates the same truth in two of his other best-known stories, "After Twenty Years" and "The Ransom of Red Chief."
"Now, Valentine," said the warden, "you'll go out in the morning. Brace up, and make a man of yourself. You're not a bad fellow at heart. Stop cracking safes, and live straight."
These words of advice to the paroled Jimmy Valentine by the warden of the prison foreshadow the redemption of Valentine. Not a "bad fellow at heart," the ex-convict who has resumed his life of crime once he has been released, but, one day, he suddenly falls in love when he encounters Annabel Adams on the sidewalk near the Elmore Bank where her father works:
"Jimmy Valentine looked into her eyes, forgot what he was, and became another man."
After this chance meeting, Valentine checks into the hotel, registering as Ralph D. Spencer, and talks to the clerk about his business venture of opening a shoe store in the town. Mr. Ralph Spencer, "the phoenix that arose from Jimmy Valentine's ashes," remains in Elmore where he secures a trade. Then, in a year he is engaged to Miss Adams and flourishes as a shoe salesman until that fateful day on which little Agatha locks herself into the bank vault. Fortunately, the reformed Jimmy saves her by unlocking the lock to this safe with his old tools which he has hoped will serve someone else.