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.

Jimmy went to Elmore because he was looking for a new location from where he could carry on with his safecracking business. Note that Jimmy has a habit of moving out of places where he has already committed a crime, perhaps so he can evade the police. Also, new places probably offer him the anonymity he needs to organize his safecracking escapades without arousing the suspicion of people. In fact, the policeman Ben Price, states that Jimmy’s “long jumps and quick getaways” among other habits, enables him to be a “successful dodger of retribution." Before Jimmy’s move to Elmore, a series of safe burglaries that bore his trademark safecracking style had taken place in Richmond, Logansport, and Jefferson City.

When he arrives at Elmore, Jimmy starts a shoe business to use as a front for his burglaries. The shoe business thrives and offers Jimmy a stability that he finds desirable. He also makes the acquaintance of the beautiful Miss Annabel Adams and falls in love with her. The two are even engaged to marry. Socially, he is well-liked and respected by many of the townspeople. He then decides to quit safecracking in order to settle down with Annabel Adams, whose father owns the Elmore bank. He is so contented with his life in Elmore that he does not crack any safes for over a year. However, a few days before Jimmy and Annabel’s wedding, an incident occurs that disturbs Jimmy’s life. At the bank, a new vault is unveiled, a ceremony to which many people are invited, Jimmy included. At the ceremony, one of Annabel’s nieces is accidentally locked inside the vault. This forces Jimmy to crack the safe to rescue the trapped girl. Through this single act of kindness, Jimmy exposes his safecracking skills to the assembled group of people.

When Jimmy Valentine descends from the "mail-hack" in Elmore, Arkansas, he soon becomes "another man": He successfully opens a shoe store and gains the love of Annabel Adams, the approval of her father, and is eventually able to completely abandon his former life.

Originally, Jimmy has been a safe cracker, but posing as a business man, he is soon Ralph D. Spencer, and rents a room at the Planter's Hotel, asking how the shoe business is in the town of Elmore and if there are any opportunities for open a store. The young clerk responds positively to him, saying that only the dry-goods store and the general stores carry shoes now. The new Ralph D. Spencer goes into action:

• Jimmy, a/k/a Ralph, opens a shoe store and does well.
• Socially he is also successful and makes many friends
• He wins the affections of Annabel Adams, the daughter of the banker
• Jimmy, a/k/a Ralph, wins Mr. Adams's approval.
• Jimmy Valentine successfully opens the safe in which Annabel's niece is trapped.
• Having been caught, he thinks, by Ben Price, Jimmy is surprisingly allowed to go free as Ben pretends that he does not know Jimmy--"Guess you're mistaken, Mr. Spencer....Don't believe I recognize you."
• He is now permanently Ralph Spencer.

Jimmy's skillful use of his burglary tools clearly demonstrates his willingness to return to prison rather than have a child suffocate. His change of character is from partial self-interest to complete unselfishness.

After Jimmy Valentine changes his name to Ralph Spencer, his transformation from thief and safe cracker to good citizen begins. This change is made because he has fallen in love with pretty Annabel Adams, the daughter of the bank president in Elmore, Arkansas, where he originally intended to rob the bank. It is also because of his love for Annabel that he decides to give away his tools to another man. This change to good citizen is partially because of his own self-interest in wishing to marry Annabel Adams.

Fortunately for nine-year-old Agatha—but unfortunately for him—Ralph Spencer happens to still have the safe-cracking tools in a supposed suitcase for his trip to Little Rock when he steps into the Elmore Bank on the day that the little girl has trapped herself inside. When Annabel pleads with her fiancé, "Can't you do something, Ralph—try, won't you?" he looks at her with "a queer, soft smile on his lips and in his keen eyes" because he knows that he must act nobly for his beloved Annabel, or lose her devotion. He also loves her and does not want her to be distraught.

So, in his most unselfish act of love, Ralph returns to being Jimmy Valentine and breaks into the vault, saving Agatha. Fully realizing that Annabel and her family now know that he has previously engaged in criminal activity, Jimmy walks out of the bank, thinking he has lost his beloved. But Ben Price rewards him for his truly loving act, aware that Jimmy is, indeed, now reformed. When Jimmy speaks to him, resigned to being arrested, Price pretends that he does not know Jimmy.

Jimmy Valentine may have been toying with the idea of going straight before he saw Annabel Adams in Elmore, Arkansas and fell in love. O. Henry plants several such suggestions.

He had served nearly ten months of a four year sentence. He had expected to stay only about three months, at the longest.

This experience must have made him realize that he was getting to be too notorious as a master safecracker. It is becoming harder for his friends to "spring" him. And it could get worse. As Ben Price observes later in the story:

Yes, I guess I want Mr. Valentine. He'll do his bit next time without any short-time or clemency foolishness.”

Jimmy has probably been thinking the same thing. He got a four-year sentence for the Springfield job, but he might get an even longer sentence the next time he gets caught. The fact that he has a record would be prejudicial against him. 

Jimmy has been working in the prison shoe shop and seems to have been enjoying it. After all, he is a craftsman, and this is just another kind of craftsmanship. This experience may have given him the notion of opening a shoe business--but he might have been thinking of just using the legitimate business as a "front."

When he tells the warden he knows nothing about safecracking and has never been in Springfield in his life, the warden just laughs. Mike Dolan just laughs when Jimmy claims he is now working for the New York Amalgamated Short Snap Biscuit Cracker and Frazzled Wheat Company. Everybody knows about Jimmy Valentine in spite of the fact that he has tried very hard to keep a low profile.

Long jumps, quick get-aways, no confederates, and a taste for good society—these ways had helped Mr. Valentine to become noted as a successful dodger of retribution. 

So when Jimmy falls in love at first sight, he is already psychologically prepared to change his identity and reform. He is able to do so because he is gifted with a superior intelligence and a winning personality. He can be just as successful as a businessman as he can as a safecracker. He tells an old friend in a letter:

I've got a nice store. I'm making an honest living, and I'm going to marry the finest girl on earth two weeks from now. It's the only life, Billy—the straight one. I wouldn't touch a dollar of another man's money now for a million.

This is the moral of the story. Honesty is the best policy. Crime does not pay. O. Henry illustrates the same truth in two of his other best-known stories, "After Twenty Years" and "The Ransom of Red Chief."

"Now, Valentine," said the warden, "you'll go out in the morning. Brace up, and make a man of yourself. You're not a bad fellow at heart. Stop cracking safes, and live straight."

These words of advice to the paroled Jimmy Valentine by the warden of the prison foreshadow the redemption of Valentine. Not a "bad fellow at heart," the ex-convict who has resumed his life of crime once he has been released, but, one day, he suddenly falls in love when he encounters Annabel Adams on the sidewalk near the Elmore Bank where her father works: 

"Jimmy Valentine looked into her eyes, forgot what he was, and became another man."

After this chance meeting, Valentine checks into the hotel, registering as Ralph D. Spencer, and  talks to the clerk about his business venture of opening a shoe store in the town. Mr. Ralph Spencer, "the phoenix that arose from Jimmy Valentine's ashes," remains in Elmore where he secures a trade. Then, in a year he is engaged to Miss Adams and flourishes as a shoe salesman until that fateful day on which little Agatha locks herself into the bank vault. Fortunately, the reformed Jimmy saves her by unlocking the lock to this safe with his old tools which he has hoped will serve someone else.

Jimmy's change was triggered by his falling in love at first sight with the beautiful and highly respectable Annabel Adams. It should be noted, however, that he was already beginning to realize that a life of crime is always a mistake. It means that the criminal becomes too well known to law enforcement officers, such as Ben Price. Judges impose harsher sentences. It is easier to get caught and harder to get out. 

He had served nearly ten months of a four year sentence. He had expected to stay only about three months, at the longest.

He also realizes that he is getting to be too well known as the best safecracker in the business. This is brought home to him when the warden seems to know all about him and when his old pal Mike Dolan asks:

“Got anything on?” 

Obviously too many people know about him and too many are talking about him. So Jimmy decides to move all the way to Arkansas, establish a business as a "front," and start operating in a virgin territory. But by chance he sees and falls in love with Annabel Adams. 

Jimmy Valentine looked into her eyes, forgot what he was, and became another man. 

He "became another man," but he was unconsciously preparing to make a radical change before that chance encounter. Annabel is a "catalyst' rather than a "cause" of his reformation. He knows he cannot win her love and remain a criminal. His experience in the shoe shop in prison gives him the idea of opening a shoe shop in Elmore, Arkansas. He is successful because of his sharp mind and winning personality. O. Henry is making the point that a man who has the talent to be a successful criminal can use the same talent to be successful if he goes straight.

In the end, Jimmy's future looks bright. He is a successful and respected citizen, engaged to marry a beautiful girl, accepted by her family and all their friends, on his way to becoming a family man, homeowner, churchgoer, and pillar of the community. He has changed his name to Ralph Spencer in order to put "Jimmy Valentine" well behind him.The change that has taken place in the old Jimmy Valentine is spelled out in the letter he writes a friend to whom he is bequeathing his set of custom-designed and custom-made safecracking tools.

Say, Billy, I've quit the old business—a year ago. I've got a nice store. I'm making an honest living, and I'm going to marry the finest girl on earth two weeks from now. It's the only life, Billy—the straight one. I wouldn't touch a dollar of another man's money now for a million. After I get married I'm going to sell out and go West, where there won't be so much danger of having old scores brought up against me. I tell you, Billy, she's an angel. She believes in me; and I wouldn't do another crooked thing for the whole world. 

For a few tense moments when Ben Price shows up at the bank, it looks as if Jimmy's dreams are  about to be smashed to ruins. But his good deed in saving the life of the little girl accidentally locked in the bank vault, makes such an impression on his nemesis that he is allowed to "retrieve" his reformation and go ahead with his idyllic new life.

In "A Retrieved Reformation," Jimmy Valentine changes when he gets to Elmore. A former safecracker who served time in jail, Jimmy falls in love with a woman named Annabel Adams and decides to give up his criminal ways. Jimmy changes his name to Ralph D. Spencer and opens a successful shoe-shop. Eventually, he woos Annabel and asks her to marry him. Jimmy also decides to give away the expensive tools he used to break into safes.

Just as Jimmy is about to be married, Annabel's father, who owns a bank, is showing the family his new safe when Annabel's five-year-old niece, Agatha, climbs into the safe and is locked inside. Discarding his respectable persona as Ralph D. Spencer, Jimmy breaks into the safe and saves the child, who could have easily died of fright or lack of oxygen. A cop named Ben Price—who has been following Jimmy—sees this incident and decides not to turn Jimmy into the authorities. In the end, Jimmy becomes a free man.

O. Henry provides many proofs that Jimmy Valentine has changed. The entire story is about how Jimmy changes from a criminal into a solid citizen. The first direct proof of his change is stated in plain words by the author.

A young lady crossed the street, passed him at the corner and entered a door over which was the sign “The Elmore Bank.” Jimmy Valentine looked into her eyes, forgot what he was, and became another man. 

Is this possible? Well, it happened pretty fast, but many young men change when they fall in love. They grow up. They realize that there is a serious purpose in life, and for most men this involves getting married, having a family, becoming a provider, having a legitimate and secure profession or a trade, assuming a respectable place in society. All of this happens to Jimmy, as O. Henry illustrates, because of his love for the beautiful and high-principled Annabel Adams.

Early in the story O. Henry describes Jimmy's suitcase in detail. It is full of his specially designed safecracking tools. The suitcase is mentioned regularly right up to the end. It is really a symbol. It identifies him as an expert safecracker, but it is also a heavy burden. When he goes straight he wants to get rid of that burden. He offers to give it to a friend and tells him the following in a letter.

Say, Billy, I've quit the old business—a year ago. I've got a nice store. I'm making an honest living, and I'm going to marry the finest girl on earth two weeks from now. It's the only life, Billy—the straight one. I wouldn't touch a dollar of another man's money now for a million. 

Then at the climax Jimmy is still burdened with his heavy suitcase and his old identity. He makes a noble sacrifice by opening the suitcase inside the bank and rescuing a little girl who has accidentally gotten locked inside the supposedly burglar-proof vault. In doing this, he knows he is losing his new identity, the girl he planned to marry, his reputation as a solid citizen, and surely going to prison for a long stretch. This is the most solid evidence that he has really become a "another man." Fortunately, Ben Price the bank detective has seen Jimmy noble deed and is himself convinced that Jimmy has changed and is no longer a threat to society. Instead of arresting Jimmy and getting him sentenced to what could be twelve years in prison for three bank jobs, Ben lets Jimmy keep his new identity. When Jimmy resignedly and despondently offers to give himself up to the law, Ben Price responds:

“Guess you're mistaken, Mr. Spencer,” he said. “Don't believe I recognize you. Your buggy's waiting for you, ain't it?”

Jimmy really has become a different man in every way, including his name. He is no longer Jimmy Valentine but Ralph Spencer, respectable small-town businessman and pillar of the community.

Jimmy Valentine had served time for breaking into a safe. He was released after serving ten months of his four year jail term. While in jail, he worked in the prison shoe shop as a shoe maker. Jimmy never did confess to breaking safes, even to the chief officer. After his release, Jimmy did not stop the criminal activities and he went ahead to break open safes at three different locations. He had developed a habit of not breaking safes in the same area which led him to arrive at a small town named Elmore.

Ben Price knew how Jimmy worked. Jimmy would go from one city to another far away. He always worked alone. He always left quickly when he was finished. He enjoyed being with nice people. For all these reasons, it was not easy to catch Mr. Valentine.

He always carried with him a bag full of his special tools for his criminal enterprise. He was bound to break a safe in Elmore, however met Annabel Adams the daughter of a local banker. He fell in love with the girl and decided to set up a shoe shop in the town.

It was the relationship with Annabel coupled with finding success in his shoe business that saw Jimmy stop his criminal activities. Annabel’s family, together with the townspeople liked Jimmy, who went by the name Spencer. He was soon going to get married and saw this as an opportunity to hand over his bag of tools to an old friend, since he was done breaking safes.

I want to give you my tools. I know you’ll be glad to have them. You couldn’t buy them for a thousand dollars. I finished with the old business—a year ago. I have a nice shop. I’m living a better life, and I’m going to marry the best girl on earth two weeks from now.

We learn that although Jimmy used to be a bank robber, he was reformed once he met the love of his life.

Jimmy seems to have been an excellent criminal with good political connections.  He serves 10 months of a four year sentence in jail, but he expected to serve much less. 

When a man with as many friends on the outside as Jimmy Valentine had is received in the "stir" it is hardly worth while to cut his hair.

He thought his friends would get him out of prison before it would be necessary to cut his hair, as they usually do when a prisoner enters the system.  Jimmy was there long enough.  The warden even says that he is “not a bad fellow at heart,” and he just needs to stop cracking safes.

Jimmy has no intention of reforming.  He goes to get a new start, but soon there were robberies with his signature.  Investigator Ben Price took notice.

Jimmy’s reformation began when he arrived in the little town of Elmore, Arkansas.

A young lady crossed the street, passed him at the corner and entered a door over which was the sign, "The Elmore Bank." Jimmy Valentine looked into her eyes, forgot what he was, and became another man. 

It was love at first sight.  It did not take long for Jimmy to become reformed, but he really was.  Ironically, he proves it by cracking a safe.  When his lovely lady’s little sister locks herself inside the safe in the bank, no one knows the combination.  Jimmy has to use his skills to rescue her.  Instead of arresting him, Price realizes that sacrifice he made and decides to let him go.  He feels that Jimmy has retrieved his reformation, and will never crack another safe to steal.