After arriving home from prison, Jimmy changes into nice clothes, grabs his burglary tools, and walks by Mike, the owner of the café where he rents a room (who is part of organized crime alongside Jimmy). When Mike subtly asks Jimmy if he’s going to rob someone, Jimmy responds using verbal irony, as seen in the following passage:
In half an hour Jimmy went down stairs and through the café. He was now dressed in tasteful and well-fitting clothes, and carried his dusted and cleaned suit-case in his hand.
“Got anything on?” asked Mike Dolan, genially.
“Me?” said Jimmy, in a puzzled tone. “I don’t understand. I’m representing the New York Amalgamated Short Snap Biscuit Cracker and Frazzled Wheat Company.”
The verbal irony here comes across in Jimmy’s “puzzled tone” in reaction to Mike’s suggestion of criminality, as well as his claim that he is “representing the New York Amalgamated Short Snap Biscuit Cracker and Frazzled Wheat Company.” This is an example of verbal irony because Jimmy and Mike both know that Jimmy is not a businessman representing the (likely fictional) company he names, but, instead, a hardened criminal going out to rob a bank.
This moment is also a subtle example of situational irony because Jimmy soon enough does go on to become a reputable businessman when he moves to Elmore and falls in love with Annabel (though he is a shoe-maker, not a representative of a “biscuit cracker and frazzled wheat” company).
The ending of “A Retrieved Reformation” is an example of situational irony. After trying to track down Jimmy for over a year, Detective Price finds him in Elmore, only to refuse to arrest the former burglar when he finally has the chance. The irony of this plot twist comes across in the final lines of the story:
At the door a big man stood somewhat in his way.
“Hello, Ben!” said Jimmy, still with his strange smile. “Got around at last, have you? Well, let’s go. I don’t know that it makes much difference, now.”
And then Ben Price acted rather strangely.
“Guess you ’re mistaken, Mr. Spencer,” he said. “Don’t believe I recognize you. Your buggy ’s waiting for you, ain’t it?”
And Ben Price turned and strolled down the street.
In this passage, both Jimmy and readers expect Price to arrest Jimmy. Not only has Price suspected Jimmy of previous thefts, but he witnesses for himself that Jimmy is still carrying around his tools and making use of them (even though, in this case, it was to save a little girl from being trapped in a safe).
When Price tells Jimmy that he’s “mistaken,” refers to him by his new name (“Mr. Spencer”), and then walks away, both Jimmy and readers are shocked. With this decision, O. Henry is suggesting that criminals can be redeemed, and that it doesn’t always (or even often) happen via the legal system. Even though it is illegal for Price to refuse to arrest Jimmy for the crimes he’s committed, the detective decides, after witnessing Jimmy’s heroic feat, that he has learned his lesson and deserves to live as a free man.
In an example of both dramatic and situational irony, Annabel pleads for Jimmy—who she believes to be a simple shoemaker named Ralph—to save her niece Agatha from being trapped inside of her father’s safe at the Elmore Bank. The layers of irony come across in the following passage, as Annabel and her family realize Agatha is trapped:
Agatha’s mother, frantic now, beat the door of the vault with her hands. Somebody wildly suggested dynamite. Annabel turned to Jimmy, her large eyes full of anguish, but not yet despairing. To a woman nothing seems quite impossible to the powers of the man she worships.
“Can’t you do something, Ralph—try, won’t you?”
He looked at her with a queer, soft smile on his lips and in his keen eyes.
This scene is an example of dramatic irony because readers know that “Ralph” is actually Jimmy Valentine, a seasoned criminal and notorious safe-cracker, while Annabel and her family do not. Thus, when Annabel begs Jimmy to “do something” and he “look[s] at her with a queer, soft smile on his lips,” readers are in on the tragic comedy of this moment with him: Jimmy knows in this moment that he can either keep Annabel in his life and let the child die or lose Annabel and save the girl by revealing his past identity as a professional burglar.
The situational irony here is that Jimmy is being asked to use his safe-cracking tools the very day that he has planned to ship them off to a friend as a sign of officially letting go of his criminal ways. After a year of good behavior and building a normal life with the woman he loves, he finds himself forced back into acting as the thieving man he used to be.
