Jimmy Valentine is hard at work in the prison shoe-shop when a guard comes to escort him to the warden’s office. Jimmy has been pardoned by the governor, and instead of celebrating, he accepts “it in a tired kind of way.” Jimmy is a connected criminal, and he expected to serve only about three months—not the ten months he actually served—of his four- year sentence. Even the prison is aware of Jimmy’s connections and his inevitable short stay, believing that when a prisoner like Jimmy “is received in the ‘stir’ it is hardly worth while to cut his hair.”
O. Henry is careful to point out that Jimmy approaches his work, even the forced labor of a prison shoe-shop, with dedication and focus, and this establishes Jimmy as a hard worker. O. Henry also establishes Jimmy as a career criminal—one with connections that reach the highest rungs of government. Jimmy knows his connections will pay off and he will be pardoned; he is only “tired” because it has taken so long. The prison too is aware of these connections, and as such, they put little effort into rehabilitating Jimmy.
The warden advises Jimmy to stop cracking safes and live straight, reminding him that he’s “not a bad fellow at heart.” Jimmy playfully denies safecracking and the warden acts along with him, defending Jimmy’s feigned innocence. The warden states that Jimmy was either treated unfairly by a biased jury, or he simply “wouldn’t prove an alibi for fear of compromising somebody in extremely high-toned society.” Jimmy continues to maintain his innocence, claiming to have never even been to Springfield, the location of his alleged crime. The warden orders the guard to obtain Jimmy new clothes for his release and to escort him to “the bull-pen” early the next morning. He then urges Jimmy to again consider his advice and live a straight life.
The warden doesn’t believe that Jimmy is inherently a bad person; rather, it is Jimmy’s job as safecracker and burglar that makes him bad. This assumption implies that hard work—work that is generally accepted as honest, that is—is essential to living a moral life. The warden’s guess that Jimmy served time because he wouldn’t give up another suggests that Jimmy has integrity and is loyal, both qualities of a good person, and Jimmy’s playful denial of his crimes cement him as pleasant and humorous. Yet Jimmy’s identity as a convict cancels out his more redeeming qualities and Henry’s use of the word “bull-pen” reinforces this. Criminals, often each painted with the same brush, are often stereotypically likened to animals by society, regardless of circumstance or individual qualities.
The next morning, Jimmy is released from the penitentiary wearing prison-issued clothing. He is given a railroad ticket and a five-dollar bill before walking out into the sunshine. Jimmy disregards the beauty of nature around him and instead immediately finds a restaurant to indulge in food, wine, and a good cigar. Before boarding a train, Jimmy tosses some pocket change into the hat of a blind man by the door.
Jimmy is terribly disadvantaged at his release. His clothes are of poor quality and he is given very few resources to re-enter society. The prison is uninvolved and indifferent regarding Jimmy’s rehabilitation, both inside and outside the prison walls. However, Jimmy is not looking to reform. He doesn’t appreciate his freedom and he immediately indulges selfishly in food and drink. Still, Jimmy’s donation to the blind man suggests that he is deeply caring and empathetic.
After three hours on the train, Jimmy arrives at a town near the Arkansas state line and goes directly to Mike Dolan’s café. There, Mike apologizes for leaving Jimmy in prison for so long. He explains that a protest in Springfield had complicated the matter and the governor was hesitant to sign the pardon. Jimmy, not particularly upset, immediately goes to his rented room above Mike’s café.
Jimmy’s interaction with Mike confirms that his prison stay was a sham and, because of this, Jimmy has very little incentive to reform. Jimmy is deeply entrenched in a life of crime, and his connections (and the government’s corruption) are indeed high-reaching. O. Henry’s mention of a protest in the town where Jimmy’s alleged crime took place, and the apprehension of the governor to pardon him, suggests that Jimmy’s crime was both serious and public.
Once upstairs, Jimmy finds his room “just as he had left it,” and notices Ben Price’s collar-button on the floor. Jimmy pulls the folding-bed down and removes a panel from the wall, revealing a dusty suitcase. He opens the case and “gazes fondly” at his set of state-of-the-art burglar’s tools, some of which he actually invented himself. A half an hour later, Jimmy appears back at Mike’s café, wearing stylish clothing and carrying his tools. Mike asks Jimmy where he is headed, and Jimmy playfully responds, claiming to be a representative for an imaginary company. Mike laughs at Jimmy’s joke, and Jimmy is so pleased with himself that he drinks seltzer-and-milk, since he never touches “hard drinks.”
Price’s collar-button serves as symbol of his dedication to his job as a lawman. As a highly respected detective, the torn button is evidence of Price’s hard work—an association that also implies Price’s high moral standing. Likewise, Jimmy’s tools symbolize his own dedication to his trade. Jimmy takes pride in his job as a safecracker, and his tools are evidence of that. He dresses nicely and presents himself professionally, despite his dishonest work. Notably, Jimmy is exceedingly pleasant and never drinks hard liquor. While his profession is certainly unscrupulous, Jimmy behaves in ways that are typically regarded as moral and good.
A week later, a safe is broken into in Richmond, Indiana “with no clue to the author,” and “a scant eight hundred dollars” is all that is taken. Two weeks after that, a burglar-proof safe in Logansport is taken for fifteen hundred dollars in cash. Strangely, the silver and securities are left behind. Lastly, a safe in Jefferson City is broken into and five thousand dollars is stolen, an amount large enough to attract the attention of detective Ben Price. Price immediately suspects Jimmy—after all, he is the only burglar with the skills and the tools to actually pull off the jobs—and he vows to arrest him and make him pay. Price is familiar with Jimmy’s handiwork and the owners of burglar-proof safes in the area immediately feel safer with Price on the job.
Price is a serious detective, only investigating high-dollar crimes, which is a direct reflection of his experience and hard work. As the suspected thief, it is remarkable that Jimmy only steals a “scant” amount of money from Richmond and leaves behind silver and securities in Logansport. This implies that he has, at least, some restraint and is not entirely greedy—until the Jefferson City job. Price is convinced Jimmy is guilty because he is the only safecracker skilled enough (and in possession of the right tools) to pull off such complicated work without leaving behind evidence, and this speaks to Jimmy’s hard work and proficiency.
Meanwhile, Jimmy, with his suitcase of burglar’s tools, hitches a ride on a horse-drawn wagon delivering mail and ends up in Elmore—a small town located in a backwoods Arkansas county, five miles away from the nearest railroad. He notices a young lady outside The Elmore Bank and instantly falls in love with her, the sight making him forget “what he was, and [become] another man.” The young lady blushes as Jimmy looks at her and is clearly attracted to him as well. Jimmy finds a boy nearby and asks him about the lady’s identity. The boy reports that the girl is Annabel Adams, the daughter of the local bank owner.
Jimmy’s arrival in Elmore is not planned—he goes there simply because the mail wagon is headed in that direction. He has his suitcase full of tools and it is clear that he is looking to crack safes; however, he doesn’t appear to have a particular safe in mind. By “forgetting” what he is, Jimmy stops being a safecracker and thief when he falls in love-at-first-sight with Annabel. Her father owns a safe that Jimmy would traditionally break into, and this marks the beginning of Jimmy’s reformation.
Jimmy walks to the nearby Planters’ Hotel and registers as Ralph D. Spencer. He claims to be in town looking for a new business venture and asks about the current shoe trade in town. The hotel clerk, impressed by Jimmy’s style and manner, informs him that there is not currently an exclusive shoe-shop in Elmore. Yet he assures Jimmy that business in town is generally good and he secretly hopes that Jimmy sets up shop. The clerk describes Elmore as a nice town with nice people. Jimmy decides to stay and books a room.
Jimmy can’t live a straight life with a crook’s identity, so he claims to be a shoe salesman, ironically falling back on his prison trade. Yet Jimmy has not completely changed his identity—he is still stylish and pleasant, and because of this, the town of Elmore is eager to accept him.
Living in Elmore, Jimmy becomes “Mr. Ralph Spencer, the phoenix that arose from Jimmy Valentine’s ashes—ashes left by the flame of a sudden and alternative attack of love.” As Ralph, Jimmy manages to build a prosperous shoe business, becomes a social success, and wins the heart and hand of Annabel Adams. They are to be married in two weeks’ time, and even Annabel’s father, Mr. Adams, approves of Ralph D. Spencer.
Jimmy did not intend to fall in love and relocate to Elmore; he intended to rob Mr. Adams’s safe and move on. Instead, he assumes a false identity and tricks Annabel into falling in love with him too. Ralph Spencer is the phoenix arising from Jimmy’s ashes because Jimmy has effectively killed the part of his identity that makes him bad, and thereby unworthy of Annabel.
Jimmy writes a letter and mails it to his old friend in St. Louis. In the letter, Jimmy requests to meet his friend next Wednesday in Little Rock to “wind up some little matters” and gift him his suitcase of burglar’s tools. Jimmy knows his friend will appreciate the tools, and since he has “quit the old business,” Jimmy no longer has a use for them. Jimmy tells his friend, Billy, about his new, honest life and his upcoming marriage to Annabel. He further tells Billy that after his marriage he intends to move West, putting more distance between himself and his past crimes. Jimmy closes by telling Billy that Annabel is “an angel,” claiming that, because of her, he wouldn’t dream of ever doing another crooked thing.
Jimmy is transformed by his love for Annabel and has no intention of ever robbing another safe—yet he still subtly hints at crime in his letter to Billy and has no problem gifting him his tools so that he can use them to rob people. Jimmy even intends to move further West so that he can continue to evade the law and avoid paying for his past crimes. Clearly, although Jimmy appears on the surface to be reformed (he works an honest job, after all), he remains unremorseful for his criminal acts.
Meanwhile, detective Ben Price quietly arrives in Elmore, still in pursuit of Jimmy for the Jefferson City break-in. He spends some time snooping about town and finds Jimmy living happily as Ralph D. Spencer. “Going to marry, the banker’s daughter, are you, Jimmy?” Ben says. “Well, I don’t know!”
Price has not forgotten about Jimmy, and after a year he is still chasing him. Price has the power to completely destroy Jimmy’s fake identity as Ralph Spencer, potentially costing Jimmy Annabel in the process.
The next day, after having breakfast with Annabel and her family, Jimmy readies himself to deliver his suitcase of burglar’s tools to Little Rock. He also has to order his suit for the wedding and he wants to buy something nice for Annabel while he’s there. Jimmy notes that he hasn’t left town since first arriving; his trip to Little Rock will be the first time. It has been a year since he pulled off the job in Jefferson City, and Jimmy figures it is safe to travel.
Jimmy’s breakfast establishes him as an accepted part of Annabel’s family, and his trip to Little Rock will serve dual purposes. Jimmy wants to buy something nice for Annabel at the same time he is deceiving her, which suggests a hidden guilt. Jimmy falsely assumes that enough time has passed since Jefferson City that Ben Price won’t still be looking for him.
Jimmy walks downtown with Annabel’s entire family, including her father, Mr. Adams, her sister, and her sister’s children, Agatha and May. Jimmy grabs his suitcase of tools from the room that he still rents at the hotel and they head to The Elmore Bank. Inside, the party goes behind the oak railings into the banking-room; “Mr. Adams’s future son-in-law is welcome anywhere.” They are greeted warmly by the clerks, and once Jimmy puts down his suitcase, Annabel picks it up and puts on Jimmy’s hat, playfully mimicking him. Annabel is surprised by the weight of the case, and Jimmy claims that it is full of shoe-horns set for return. He is delivering them himself in order to avoid an express charge, since he is becoming more concerned about spending money.
Jimmy is not merely accepted by Annabel’s family, but is accepted in particular by Mr. Adams. So much so that he allows Ralph inside his bank, behind the railings that separate the general public from the money. Ironically, Jimmy is treated like royalty by the bank tellers under the guise of Ralph Spencer; however, Jimmy’s true identity is contained in his suitcase, which he must continue to lie about in order to remain in Mr. Adams’s good graces. Furthermore, Jimmy is only concerned about spending money because he now has to work for it.
The bank has just installed a new safe and vault, and Mr. Adams wants to show it off. While small, the vault is equipped with a state-of-the-art door, solid steel bolts, and a time-lock. Mr. Adams explains the inner workings of the safe to Ralph, who shows “a courteous but not too intelligent interest.” May and Agatha are clearly fascinated by the metal knobs and clock.
Jimmy is incredibly knowledgeable about safes and vaults, and he must be careful not to give himself away and draw suspicion to his identity as Ralph Spencer. Mr. Adams is so involved in explaining the safe that he doesn’t notice May and Agatha’s interest.
As Mr. Adams engages Ralph, bragging about his new safe, Ben Price walks undetected into the bank. He stands around casually and tells the teller behind the desk that he is just waiting for a man he knows.
Unbeknownst to Jimmy, Ben Price is still in pursuit of him for the Jefferson City robbery. Ben is patient and calculated as he closes in on Jimmy.
Suddenly, Annabel and her sister scream. Without their knowledge, May has locked Agatha in the safe while playing. Mr. Adams tries to open the vault, but he has not yet set the clock or the combination and he is unable to disengage the lock. Annabel’s sister, worried that her daughter will suffocate to death in the safe, panics and demands the men do something. Mr. Adams responds, “There isn’t a man nearer than Little Rock who can open that door.” He turns to Jimmy, desperately seeking advice on how to proceed, but resigns himself to the worst. Annabel, not entirely hopeless, blindly begs, “Ralph—try, won’t you?”
Despite giving Ralph a detailed description of his safe, Mr. Adams is not able to open it and Agatha is running out of air. Ironically, Mr. Adams claims that anyone who could open the safe is miles away, while standing next to the best criminal safecracker around. Annabel has no reason to believe that Ralph has the knowledge to open the safe, yet she believes in Ralph—the very thing that Jimmy credits as his reason for leaving “the old business” in his letter to Billy.
Smiling, Jimmy asks Annabel for the rose that is pinned to her dress. Confused, Annabel unpins the rose and hands it to Jimmy. He puts it in his pocket, takes off his coat, and rolls his sleeves up, and “with that act Ralph D. Spencer passed away and Jimmy Valentine took his place.” Jimmy orders everyone away from the safe and begins to remove the tools from his suitcase.
Jimmy asks for Annabel’s rose, a symbol of their love, as a way to remember her. Annabel is not guaranteed to still love Jimmy once she learns of his true identity, and Jimmy can’t crack the safe without casting some doubt onto his life as Ralph. Once Jimmy opens the suitcase of tools and begins to crack the safe, he can no longer convincingly pretend to be merely a shoe salesman.
As Jimmy begins to work, freeing Agatha from the safe, he seems to be unaware of those around him. He methodically removes the strange tools from his bag and whistles as he works. Jimmy is silent and appears “immovable” while “the others watch him as if under a spell.” Jimmy opens the safe in ten minutes flat, breaking his current record. Agatha, thankfully, is safe on the other side of the door. She collapses on the floor and is picked up by her mother.
As Jimmy begins to crack the safe, he easily settles back into his true identity. He is a skilled safecracker, and this is obvious to those around him. He whistles because he truly enjoys cracking safes, and he is able to free Agatha quickly—quicker than he has ever cracked a safe before. Jimmy uses his criminal skills for good—despite the risk it poses to his false identity—and it is in this moment that he is truly redeemed.
Jimmy puts on his coat and begins to walk toward the other side of the oak railing. As he walks, he hears an unmistakable voice yell, “Ralph!” He turns around without hesitating.
As Jimmy attempts to leave the bank, certain that Annabel’s love is lost, he recognizes Ben Price’s voice and resigns himself to his punishment—now ready to accept it.
Ben Price stands blocking the front door of the bank. Jimmy greets Price warmly with a smile, stating, “Got around at last, have you? Well, let’s go. I don’t know that it makes much difference, now.” Ben begins to behave in a peculiar way and pretends not to recognize Jimmy. “Guess you’re mistaken, Mr. Spencer,” Price says, before turning and walking out of the bank.
Price stands by the door to ensure that Jimmy sees him, and Jimmy is not surprised to discover that he is still pursuing him. Redeemed and certain that Annabel will reject him, Jimmy does not attempt to elude Price. Surprisingly, after witnessing Jimmy’s redemption, Price lets him go—effectively breaking the law in the process—suggesting that what is right or good may not always be legal.