The story’s point of view shifts from Jimmy to an objective perspective. A week after Jimmy’s release, a safe is broken open and eight hundred dollars is stolen in Richmond, Indiana, and no one knows who did it. Two weeks after that, a particularly strong safe in Logansport is opened and fifteen hundred dollars is stolen. The next broken safe is in Jefferson City, where five thousand dollars is taken.
Ben Price, a detective assigned to the case, visits the broken safes. He is overheard saying that Jim Valentine is in business again, based on the skill and precision of the break-ins. Ben Price says Jimmy is the only person with the tools and knowledge to commit such clean robberies. Ben Price says he wants to catch Jimmy and put him in prison; this time, he will serve his full sentence.
But Ben Price knows Jimmy is not easy to catch, since he works alone, moves from the last city to another far away, and is kind to people he meets along the way. Nonetheless, safe owners are pleased that Ben Price is on the case.
The narrative returns to Jimmy as he and his case arrive one afternoon in Elmore, a small town in Arkansas. The youthful-looking Jimmy walks toward a hotel. He notices a young woman entering the Elmore bank. He looks into her eyes and forgets his identity as a safe breaker; he becomes another man. She looks away and blushes. Jimmy asks a young boy near the bank door if she is Polly Simpson, and the boy says she is Annabel Adams, the bank owner’s daughter.
At the Planters' Hotel, Jimmy checks in under the name Ralph D. Spencer. He says he is in town because he wants to open a shoe shop, and asks what the shoe business is like in Elmore. The hotel employee approves of Jimmy’s clothes and manners, and so is happy to talk. He confirms that Elmore needs a good shoe shop. Jimmy insists on taking his own bag to his room due to its weight.
Under the identity of Ralph Spencer, Jimmy stays in Elmore and starts a shoe shop. Business is good. He makes friends and pursues a relationship with Annabel Adams, whom he likes better every day.
By the end of the year, everyone in town admires Ralph Spencer, his shoe shop is thriving, and he and Annabel are engaged to be married in two weeks. Mr. Spencer is welcomed into the Adams family.
Jimmy writes a letter to an old friend named Billy. In the letter, he arranges to meet the friend at Sullivan’s place in Little Rock the next week, on the evening of the 10th. Jimmy would like to give Billy his tools, explaining that he is done with the old business of safecracking. He has a profitable shop and a girl he loves; he would never touch another man’s money again. He writes that, after he marries, he plans to move to the West where no one will know him as James Valentine. He closes the letter by saying how wonderful Annabel is, and that she believes in him.
Jimmy sends the letter. The following Monday, Ben Price arrives in Elmore. He moves slowly through the town, quietly collecting information. While Ben is standing in a shop, he sees “Ralph D. Spencer” walk by. Speaking to himself, Ben says that Jimmy shouldn’t feel so sure about his plan to marry the banker’s daughter.
After the first section of the story establishes that Jimmy’s safe-cracking career will start again, the narration shifts away from Jimmy’s point of view to explain that three safes have been broken into. The difficulty of the safe-cracking and the sum of money taken both escalate with each new case.
Ben Price is introduced as Jimmy’s antagonist. He is familiar with Jimmy’s notorious safe-cracking ability and suspects Jimmy right away. He plots to capture Jimmy and put him away for a longer sentence. By showing that a detective is on the case, O. Henry establishes dramatic irony, as the reader knows someone is coming for Jimmy while Jimmy presumably remains ignorant.
The dramatic tension carries forward when the point of view returns to Jimmy, who has just arrived in Elmore when he sees a young woman. Jimmy’s attractive appearance causes her to blush. In an instance of situational irony, Jimmy becomes infatuated with the bank owner’s daughter; the look they share is enough for Jimmy to discard his identity as a safe-cracker. The theme of identity arises: employing the shoemaking skills he honed in prison, Jimmy invents a new identity as Ralph Spencer, an honest shoe seller.
As Jimmy ingratiates himself in Annabel’s family, the reader suspects that Jimmy’s duplicitous identity will soon reemerge, and that his new life is merely an act designed to get him access to the Elmore bank safe. Even Jimmy’s letter to his friend Billy, in which he claims to be reformed, seems suspicious. A question is put in the reader’s head: is Jimmy actually capable of reform, or is the reader being duped, just as the Adams family is? It is also unclear why, if Jimmy was truly reformed, he wouldn’t simply discard his tools. His desire to give them to a friend suggests that Jimmy, despite his apparent reform, is nonetheless interested in maintaining good relations with this support network.
Ben Price’s arrival in Elmore reignites the dramatic irony established at the beginning of the section. Just as Jimmy has secured his new and happy life, the detective who once arrested him turns up to thwart Jimmy’s plans and expose his false identity.