There are two good examples of irony involving Jimmy Valentine's reformation. One is that his past catches up with him just when he has decided to reform. The three safecracking jobs he pulls after his release from prison net him enough money to open a shoe business in Elmore, Arkansas. At first he only wants the business as a "front," to make himself look like a legitimate businessman while he continues to loot banks in that region. But then he falls in love with Annabel Adams at first sight and decides to go straight. While he is making this great psychological change, his nemesis Ben Price is investigating the three bank jobs.
Ben Price investigated the scenes of the robberies, and was heard to remark: “That's Dandy Jim Valentine's autograph. He's resumed business. Look at that combination knob—jerked out as easy as pulling up a radish in wet weather. He's got the only clamps that can do it. And look how clean those tumblers were punched out! Jimmy never has to drill but one hole. Yes, I guess I want Mr. Valentine. He'll do his bit next time without any short-time or clemency foolishness.”
This kind of situational irony is used in O. Henry's "The Cop and the Anthem." Just when Soapy decides that he will give up the life of a bum and become an honest working man, a cop arrests him for vagrancy and loitering and he is sentenced to three months in jail. He gets the "vacation" he wanted when he no longer wants it.
Another example of irony in "A Retrieved Reformation" is found in the scene in which Jimmy Valentine sacrifices his fiancee, his successful new business, and his reputation to save a little girl who has become accidentally trapped inside a bank vault. What is ironic is that Jimmy is cracking a burglar-proof safe to do a good deed and his good deed is likely to get him arrested and sent to prison for many years. It is doubly ironic that his good deed actually saves him from going to prison for the three bank jobs for which Ben Price is there to arrest him.
"A Retrieved Reformation" is full of ironies. It is ironic that the girl Jimmy falls in love with is the daughter of the owner of the town's bank. It is ironic that he should use the skills he learned in prison to open a shoe business in Elmore as a "front," and then it is ironic that the shoe business should become so prosperous that he doesn't need to be a criminal anymore. It is ironic that his suitcase full of heavy, specially designed safecracking tools should be indispensable to his success as a crook and then should become a heavy burden he can't seem to get rid of. It is ironic that his success as a safecracker should make him so famous that it brings the law down upon him. Life is full of ironies, and O. Henry's stories are full of ironies too.