When "A Retrieved Reformation" opens, Jimmy Valentine has been serving time in a state prison for a safecracking job in Springfield, Illinois. He received a four-year sentence but was pardoned by the governor of that state through the influence of Jimmy's many important friends on the outside. But he had committed a great many other such crimes before he got caught in Springfield. He has become notorious as the best safecracker in the country. Once he gets out of prison he gets his specially designed tools and goes back to work. O. Henry describes the three crimes he commits after his release.
A week after the release of Valentine, 9762, there was a neat job of safe-burglary done in Richmond, Indiana, with no clue to the author. A scant eight hundred dollars was all that was secured. Two weeks after that a patented, improved, burglar-proof safe in Logansport was opened like a cheese to the tune of fifteen hundred dollars, currency; securities and silver untouched. That began to interest the rogue-catchers. Then an old-fashioned bank-safe in Jefferson City became active and threw out of its crater an eruption of bank-notes amounting to five thousand dollars. The losses were now high enough to bring the matter up into Ben Price's class of work.
These are apparently the only crimes Jimmy commits after his release from prison. He falls in love with Annabel Adams in Elmore, Arkansas, and decides to go straight. Ben Price is Jimmy's nemesis. It was Price who arrested Jimmy for the safecracking job in Springfield. These were the days before the federal government got involved in insuring funds deposited in banks, so banks used private agencies like the Pinkerton National Detective Agency for protection. Ben Price is evidently a private detective and not a lawman.
O. Henry writes about his subject with authority. He himself served several years in prison for embezzlement before he became a famous writer. He learned a great deal about the lives and methods of criminals from the men he was forced to associate with in prison.
One of the most painful realities that Jimmy Valentine did in Henry's short story is that he was a safe cracker. He broke into safes and vaults that were not his and took money that did not belong to them. Another "bad" thing that Valentine did was steal money. Jimmy Valentine took money and material elements that did not belong to him. This helps to constitute some of the most significant bad things that Jimmy Valentine did.
Jimmy leaves prison, lying to the Warden, in an almost sarcastic manner in claiming his innocence. The Warden acknowledges that Jimmy is “not a bad fellow at heart.” However, the focus of narrative is not really how "bad" Jimmy is. If anything, Henry's story speaks to how Jimmy is not a "bad fellow." Rather, Jimmy shows to be a person willing to embrace change and demonstrate this in his actions since his imprisonment. While Jimmy has done some bad things in his life, Henry's short story reflects how human beings can change even when they might have committed bad acts at another point in time in their lives. The capacity to change becomes the focal point of the narrative. The emphasis on the "bad things" that Jimmy Valentine did at one point in his life is not as important as the emphasis on he is capable of change, reflective of how all human beings can display the capacity to change.