What are examples of irony involving Jimmy Valentine in "A Retrieved Reformation"?

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. 

How does verbal irony foreshadow Jimmy Valentine's intentions in "A Retrieved Reformation"?

In “A Retrieved Reformation,” O. Henry utilizes verbal irony to foreshadow the protagonist Jimmy Valentine’s return to a life of crime. Verbal irony is when a speaker says the opposite of what they really mean.

“A Retrieved Reformation” opens with Jimmy making shoes in the prison shoe shop. The reader does not yet know why Jimmy is in jail. While releasing the Jimmy, the chief prison warden tells the soon-to-be ex-con to straighten out, live a law-abiding life, and stop breaking into safes:

“Me?” said Jimmy in surprise. “I never broke open a safe in my life.”

His statement provides the first clue as to why Jimmy has been incarcerated in the first place. Jimmy’s question and assertion also provide an example of verbal irony. Right away, the reader suspects that Jimmy is feigning surprise and innocence with a “Who, me?” tone. Yet Jimmy and the officer know that he has committed the crime, as if the question and statement comprise a joke they both share—and know is facetious.

After the officer laughs and proposes preposterous alternative reasons for the protagonist’s incarceration (e.g., the judge simply disliked him), Jimmy repeats:

“Me?” His face still showed surprise. “I was never in Springfield in my life.”

In this second statement and example of verbal irony, O. Henry provides more detail—the location of the crime that sent Jimmy to jail. This verbal irony foreshadows the protagonist’s future intentions and actions.

Jimmy quickly and obviously reveals that he is not interested in reforming his criminal ways. He immediately returns to his friend Mike Dolan to retrieve his beloved bag filled with tools that were custom-designed and constructed for breaking into safes.

Within a half hour after his arrival home, Jimmy is ready to leave again, this time with his precious tools. Seeing Jimmy with the telltale bag, Mike asks him what he has planned:

“Me?” asked Jimmy as if surprised. “I don’t understand. I work for the New York Famous Bread and Cake Makers Company. And I sell the best bread and cake in the country.”

This repetition of a fake expression of surprise,and a statement of denial is the third example of verbal irony, yet this instance confirms what the earlier statements predicted—that Jimmy intends to return to his former vocation of cracking safes to steal money. Obviously, he is not planning on selling bread and cake!

Soon afterward, bank safes across the country are broken into and cleared out:

A week after Valentine, 9762, left the prison, a safe was broken open in Richmond, Indiana. No one knew who did it. Eight hundred dollars were taken.

By this time, the reader, Jimmy, and O. Henry know who did it—Jimmy. The character’s earlier statements, dripping with verbal irony, all foretold he would.