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30 pages 1 hour read

O. Henry

A Retrieved Reformation

Fiction | Short Story | Adult | Published in 1903

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Character Analysis

Jimmy Valentine / Ralph D. Spencer

Jimmy Valentine is a round, dynamic character. He is the protagonist of “A Retrieved Reformation”—a handsome man with connections in high places and a love of the finer things of life. He’s also a consummate criminal, a notorious safecracker and convicted felon whose life of crime is undone by unexpected love.

The third-person omniscient narrator first introduces “Valentine, 9762,” a convict working in the prison shoe-shop. Jimmy’s time in prison ends with a pardon from the governor. Once free, he quickly returns to his old ways, drawing the attention of the police detective who put him behind bars. Jimmy has a quick wit and a sense of ironic humor. When the warden refers to his arrest in Springfield, Jimmy is “blankly virtuous,” claiming, “Why, warden, I never was in Springfield in my life!” (1).

Jimmy’s custom set of burglar tools is a prized possession, and he carries them with him wherever he goes. He is also a fancy dresser, which earns him the nickname “Dandy Jim Valentine” (2) and the envy of people like the hotel clerk in Elmore, Arkansas. Jimmy’s tools and clothes thematically reflect Identity and Transformation, and shoes are a key symbol of Jimmy’s redemption.

Although Jimmy is a professional criminal, he has the potential to change. In prison, the warden tells Jimmy that he’s “not a bad fellow at heart” (1), which proves true when Jimmy chooses a life with Annabel over a lucrative life of crime. Jimmy cares about others, even to the point of sacrificing his own future to save Agatha from the bank vault. In breaking out his burglar tools to open the vault, he willingly abandons his persona as Ralph D. Spencer and everything that goes with it, only to reclaim that identity when Ben Price chooses not to arrest him.

Ben Price

Ben Price is a round, dynamic character and Jimmy’s antagonist. Although the two men are foils, they share important characteristics. Price is as much a career police officer as Jimmy is a career criminal. He was responsible for Jimmy’s arrest in Springfield, where he lost a shirt button in the struggle. Price is dedicated to upholding the law and believes that Jimmy’s convenient pardon means justice has not been served. When Jimmy returns to his criminal ways, Price becomes determined to make him “do his bit next time without any short-time or clemency foolishness” (2).

Price also has a heart, and he recognizes goodness in Jimmy when the safecracker abandons the safety of his new identity to save Agatha. Although Price is committed to upholding the law, he breaks his own rules and allows Jimmy to go free.

Mike Dolan

Jimmy’s friend Mike Dolan is a flat, static character who makes only a small appearance in the story. However, his presence adds important context and backstory. Mike Dolan runs a café and rents Jimmy a room upstairs. Mike is also a trusted colleague who was responsible for arranging Jimmy’s pardon, and he explains why it took longer than expected: “Sorry we couldn’t make it sooner, Jimmy, me boy […] But we had that protest from Springfield to buck against, and the governor nearly balked” (1). Mike has kept Jimmy’s room just as it was when he was arrested, and he made sure Jimmy’s expensive tools are safe.

Mike functions as Jimmy’s confidant. He is the first person Jimmy turns to upon his release from prison, and he also shares Jimmy’s sense of ironic humor. When Jimmy blandly says that instead of returning to safecracking, he’s representing a couple of nonsense companies, “this statement delighted Mike to such an extent that Jimmy had to take a seltzer-and-milk on the spot” (2). Mike’s response suggests that Jimmy plans to resume his criminal endeavors and highlights Jimmy’s culpability in the string of burglaries that occurred after his release from prison.

Annabel Adams

Annabel Adams is a flat, static character. She is the daughter of Elmore’s banker and Jimmy’s love interest. When Jimmy sees her for the first time, he “looked into her eyes, forgot what he was, and became another man” (2). Annabel’s interest is also piqued by Jimmy’s presence. Because “young men of Jimmy’s style and looks were scarce in Elmore,” she responds by “lower[ing] her gaze and color[ing] slightly” (2).

When Annabel leaves the bank a short time later, she studiously ignores him. As Jimmy establishes himself in Elmore under the pseudonym Ralph D. Spencer, the two become acquainted and later engaged. Annabel continues to be Jimmy’s moral compass and his support as he builds a future as Mr. Ralph Spencer. In the letter to his old friend Billy, Jimmy credits Annabel for his decision to pursue a straight life: “[S]he’s an angel. She believes in me; and I wouldn’t do another crooked thing for the whole world” (3).

Annabel next appears as Jimmy is preparing to travel to Little Rock to dispose of his safecracking tools. With her wedding just two weeks away, Annabel’s heart is “bubbling with happiness and lively youth” (4). Her lighthearted clowning with Jimmy’s hat and suitcase full of tools hints at events to come: “My! Ralph, how heavy it is? Feels like it was full of gold bricks” (4).

When Agatha becomes trapped in the vault and no one seems able to free her, Annabel turns to Jimmy and asks him to help: “Can’t you do something, Ralph—try, won’t you?” (4). Just as her first appearance caused Jimmy to become another man, her appeal at this moment causes him to return to the man he was.

Although Annabel’s appearances in the story are few, she plays a powerful part as the catalyst for Jimmy’s transformation, his decision to pursue the “straight” life, and his ultimate return to his former self.

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