The story “A Retrieved Reformation” is a classic redemption narrative, and its protagonist, Jimmy Valentine, is an archetype of a classic American fictional character. Jimmy is a goodhearted safecracker who is transformed by love into a model small-town businessman, an O. Henry version of the proverbial leopard who changes his spots.
Directly after being released from a short prison term, Jimmy goes to see an old associate and retrieve his safecracker tools, equipment well-known to the detective always on Jimmy’s trail. Jimmy then embarks on a crime spree, taking him across Missouri and eventually over the Arkansas border to the small town Elmore.
Jimmy comes to Elmore because it’s close to the railroad for an easy getaway if needed, and such an ordinary place that Ben Price and the authorities wouldn't suspect that he’d be hiding out there. O. Henry implies subtly that Jimmy intends at first to rob the Elmore Bank, before he finds out the girl he’s just fallen in love at first sight with is the banker’s daughter. From that moment, we’re told, he “looked into her eyes, forgot what he was, and became another man.” The man he became, right then and there on the spot, was Ralph Spencer, newly arrived to open the town’s first specialty shoe store.
At this point, we don’t know for certain what Jimmy’s true motives are. Has he really experienced such a profound change of heart, or is he just deceiving Annabel and her family to gain close access to the bank? We don’t know for sure until we get to read Jimmy's letter at the twist ending, which is what makes the writing and characterization so effective.