Written in a third-person omniscient voice, O. Henry’s “A Retrieved Reformation” opens on the protagonist, Jimmy Valentine.
Jimmy is stitching the upper portion of shoes in a prison shoe shop when a prison officer brings him to the prison office. At the office, Jimmy is given a pardon letter, which he responds to with an apparent lack of interest. Jimmy has served ten months of a four-year sentence, but he had expected to serve only three months. Jimmy has a network of friends outside the prison, and he had believed they would have freed him sooner.
The prison warden tells Jimmy that he is a good man at heart and that his release is an opportunity to make a man of himself; if Jimmy would stop breaking safes open, he could live a better life. Jimmy feigns innocence, acting surprised at the suggestion he has ever cracked a safe. The warden laughs, and asks how Jimmy ended up getting sent to prison for opening a safe in Springfield. The warden suggests maybe Jimmy hadn’t wanted to tell the judge his alibi, or perhaps the court simply didn’t like Jimmy. The warden says that men like Jimmy always have some excuse, and that they never admit to their guilt.
Jimmy continues to act surprised and claims he has never been to Springfield. The warden orders Jimmy to be taken away and given new clothes in preparation for his morning release. He tells Jimmy to think about what he said about making himself a better man.
The next morning, Jimmy is back in the office wearing new but poorly fitted clothing and shoes. The prison gives him money for a train ticket to town and an extra five dollars to start his new life as a better man. The warden shakes Jimmy’s hand and gives him a cheap cigar. Jimmy, losing his identity as Prisoner 9762, walks out into the sunshine as Mr. James Valentine.
Jimmy ignores the birdsong, verdant trees, and flowers as he heads straight to a restaurant to taste his freedom. After eating broiled chicken and drinking a bottle of white wine, he heads to the train station, stopping to give a quarter to a blind beggar before boarding the train. Three hours later he arrives in an unnamed small town and goes to Mike Dolan’s café. Mike Dolan is alone. They shake hands and Mike apologizes for not having freed Jimmy sooner, explaining that the charge against him for the safe-breaking in Springfield made it difficult.
Everything is as Jimmy left it in his room at the back of the house above Mike’s café. A collar button on the floor had been torn from a cop’s named Ben Price's coat, evidence of the struggle that occurred when Jimmy fought to escape arrest in the room.
Jimmy pulls his bed from the wall. Jimmy opens a secret panel and withdraws a dust-covered suitcase full of safe-breaking tools. He looks lovingly at the tools, which he had designed himself and paid a specialist to fabricate out of special material, in the necessary shapes and sizes. The set cost over nine hundred dollars.
Half an hour later, Jimmy walks downstairs. He is wearing good clothes and he has cleaned the dust off the case, which he carries. Mike asks if Jimmy has any plans. Affecting the same surprise he used with the warden, Jimmy claims not to understand the question and says he works for the New York Amalgamated Short Snap Biscuit Cracker and Frazzled Wheat Company. Mike is delighted by Jimmy’s response and pours him a seltzer and milk, since Jimmy never drinks hard alcohol.
The story opens by introducing the reader to Jimmy’s enigmatic personality. Jimmy first undermines the reader’s expectations of conventional behavior when he reacts to the news of his release with a perplexing disinterest. When speaking to the warden, Jimmy playfully feigns ignorance in a way that patronizes the warden's intelligence. This condescension suggests that Jimmy doesn’t fear the warden's authority, and has no interest in the warden's claim that Jimmy could reform himself. It is clear—or at least seems clear—that Jimmy and the chief abide by different moral codes.
The theme of identity emerges when Jimmy leaves the prison, shedding his identity as a numbered prisoner and rejoining civil society as Mr. James Valentine. Jimmy’s enigmatic character is further developed when we learn he has no interest in the beauty of the free world, suggesting that he is perhaps used to being released from prison, and that the two worlds aren’t much different in his eyes.
Jimmy does, however, enjoy good food; rather than put the extra five dollars toward starting his new life, Jimmy spends it on a restaurant meal, giving some change to a blind beggar. The juxtaposition of these two expenditures—one lavish, the other charitable—further complicates the reader’s idea of who Jimmy is, and what his motivations are. This glimpse of Jimmy’s charitable self speaks to the warden's claim that Jimmy has a good heart, while also foreshadowing Jimmy’s eventual selfless act when he risks revealing his identity to save Agatha.
The introduction of Mike Dolan goes some way toward explaining how Jimmy was freed from prison, though what exactly Mike did to convince the governor remains a mystery. Jimmy’s enigmatic nature is further revealed with the introduction of his hidden safe-breaking tools. The motif of Jimmy’s respectable appearance is introduced when he walks back downstairs in decent clothes; his pleasing appearance is significant because it helps him to gain people’s trust, which he can exploit when arriving in new towns to break open safes.
Jimmy's playful and casual duplicity arises again when Mike asks him what his plans are. Jimmy, already in character, answers by giving the false identity he plans to assume. Jimmy’s determination is showcased in the fact that he never drinks strong alcohol, which suggests that Jimmy remains sober to disallow any vulnerability. The section ends by injecting a new tension into the story: prison has done nothing to deter Jimmy from restarting his safe-cracking career, and the warden's claim of possible reform had been misguided.