It does not seem likely that Jimmy Valentine returned to a life of crime. He had too many reasons for wanting to reform and stay reformed.
- He had a narrow escape when Ben Price decided not to arrest him. Price wanted him for three safecracking jobs in Indiana. Jimmy had been sentenced to four years in prison just for one such job, so he could have gotten as much as twelve years in prison for three. This experience should have taught Jimmy how much he values freedom and the good life on the outside.
- Jimmy could still have married Annabel Adams even though she had found out that he was a professional safecracker. If Ben Price could forgive him, then Annabel and her father could too. There would be a lot of explaining to do, but she loves Jimmy and would trust him to reform, especially in view of the heroic sacrifice he had made when he freed the little girl trapped in the bank vault.
- Jimmy was giving up his set of safecracking tools.
- Jimmy was making a good living in the shoe business in Elmore.
- Jimmy was deeply in love with Annabel. They would be married and have children. He would become a family man and a pillar of society.
- Jimmy was beginning to realize that his life of crime was getting harder and harder to maintain. He thought he would get pardoned after serving only four months of his sentence, but he actually served ten months. His friend Mike Dolan tells him: "Sorry we couldn't make it sooner, Jimmy, me boy,” said Mike. “But we had that protest from Springfield to buck against, and the governor nearly balked. Feeling all right?” This is significant. It shows that Jimmy will find it easier and easier to get arrested and harder and harder to get pardoned or paroled. He is building a big reputation as the best safecracker in the business, but this is becoming a serious handicap. Ben Price recognizes his handiwork and has no trouble tracking him to Elmore. Everybody knows about Jimmy and talks about Jimmy, in spite of the fact that he tries to keep a low profile.
- Jimmy knows his reformation is a last chance for him to change his ways. His reformation was like a miracle. He fell in love at first sight. He started a successful shoe business. He established a whole new identity. Everything worked out perfectly for him in Elmore. Such miracles do not occur often. Jimmy was on a slippery slope and didn't realize it until it was almost too late. O. Henry's story is intended to show that it isn't easy for a criminal to reform. Jimmy is still a young man. He can still change his attitude, and that is the most important part of reformation.
If Jimmy returned to a life of crime he would be sure to get caught. O. Henry makes that clear in various ways. Jimmy is the first person every cop would suspect for every safecracking job in the Midwest. His success has depended on his remaining anonymous. He flees to Elmore, Arkansas, because he is trying to establish a "front" and a new identity. But Ben Price finds him there. Jimmy couldn't remain married to Annabel and resume a life of crime. She wouldn't tolerate it. He would have little to gain from burglarizing banks and a lot to lose. The best evidence of Jimmy's real reformation is contained in the letter he sends to an old pal to whom he plans to give his custom-made safecracking tools.
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. I tell you, Billy, she's an angel. She believes in me; and I wouldn't do another crooked thing for the whole world.
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