Can A Thief Change His Ways?

O. Henry’s story teaches that having undergone a process of cheshbon nefesh (soul-searching), regret and teshuva (repentance), even a criminal can become a good person.

Resource Ages: 12-14


A Retrieved Reformation

By: O. Henry

Jimmy Valentine is a successful bank robber and a master of his trade. One day, though, Jimmy is caught in the act and put in jail. After his release, he goes home and plans to get back to work…

He got his key and went upstairs, unlocking the door of a room at the rear. Everything was just as he had left it. There on the floor was still Ben Price’s collar-button that had been torn from that eminent detective’s shirt-band when they had overpowered Jimmy to arrest him.

Pulling out from the wall a folding-bed, Jimmy slid back a panel in the wall and dragged out a dust-covered suit-case. He opened this and gazed fondly at the finest set of burglar’s tools in the East. It was a complete set, made of specially tempered steel, the latest designs in drills, punches, braces and bits, jimmies, clamps, and augers, with two or three novelties, invented by Jimmy himself, in which he took pride. Over nine hundred dollars they had cost him to have made at —-, a place where they make such things for the profession.

In half an hour Jimmy went down stairs and through the cafe. He was now dressed in tasteful and well-fitting clothes, and carried his dusted and cleaned suit-case in his hand.


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Foundations for Planning

Essential Questions

  • How can I be the best “me” this year? In class, at home, on the playground, etc?
  • How can a person’s decisions and actions impact his/her life?

Content Questions Related to the Essential Questions

  • To what extent can someone really change their life?
  • What factors may encourage someone to work to improve themselves, and what factors can thwart such an attempt?
  • Does remorse atone for our actions?
  • In general, what makes people want to change?
  • Should someone be punished for their actions even after they have repented?

Background for Teacher

Henry was the penname of the American writer William Sidney Porter (1862-1910) further reading.  “A Retrieved Reformation” tells the story of Jimmy Valentine, a bank robber who after a series of experiences decides to change his life and reform himself. The turning point in...

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Henry was the penname of the American writer William Sidney Porter (1862-1910) further reading.

 “A Retrieved Reformation” tells the story of Jimmy Valentine, a bank robber who after a series of experiences decides to change his life and reform himself. The turning point in the story comes when he is together with his fiancée, who knows nothing of his past. In order to save her niece, who is trapped in a safe, he uses his old burglary tools, which he was about to give away and not to use again. A police detective who has been tracking him and planned to apprehend him sees what happens and decides on the spot not to arrest Jimmy.

The end of the story reflects the view that through his act of caring for another, Jimmy showed that he had fully repented, and accordingly did not need to pay his debt to society. In the class discussion, the students may agree or disagree with this approach.

In-Depth Discussion
Suggested Activities
Further Study

Click here to view our consolidated list of suggested interactive pedagogies for classroom discussion.

  1. What factors can encourage someone to improve themselves and what factors can thwart this process?
  2. What made Jimmy Valentine change? 
  3. The detective Ben Price chose not to destroy Jimmy Valentine’s new life after he watched him save the girl. Why do you think he acted in this way? Do you agree with Ben? Do you think he behaved properly? Explain your position. 
  4. Should someone who has repented still be punished for their past?
  5. Does someone who has changed still remain basically the same person?
  • Stop telling the story immediately after Jimmy leaves the bank and sees the detective, without revealing the end of the story to the students. Ask them to make up an ending for the story, explaining what happened when Jimmy met Ben, and to explain their choice. Now read the actual ending. Hold a discussion: Ask the students to put themselves in the shoes of Jimmy or the detective, and then back in their own shoes. Ask them to imagine that they were in a situation where they had regretted something they did, but other people still saw them as guilty; or to imagine that they saw that someone had repented, but they were still angry about what they did. How would they behave? In other words – ask themselves to put themselves in Jimmy’s shoes and then in their own shoes as an individual.
  • Hold a play in the class featuring a confrontation between Jimmy and Annabel after the story. He explains why he had the burglary tools. What does he say? How does she react? Invite the students to switch roles and present different scenarios.
  • Draw a parallel between the story and some verses from the Yom Kippur prayers:
    “Though your sins be as scarlet, they shall be as white as snow; though they be red like crimson, they shall be as wool” (Isaiah 1:18).
    Explanation: even though your sins are bright red and evil, true remorse can make them clean and pure.
    “For on this day shall atonement be made for you, to cleanse you; from all your sins shall you be clean before God” (Leviticus 16:30).
    Explanation: On Yom Kippur God forgives the sins of those who have truly repented. “And repentance and prayer and charity remove the harsh decree” (from the Unetaneh Tokef prayer).
    Explanation: these actions help to atone for the harsh divine punishment.These verses are included in the service in order to emphasize the strength of repentance and remorse. Even the gravest of sins can be wiped clean if the individual is truly sorry. Discuss the similarity between these verses and the way Ben Price behaves toward Jimmy.
  • Study the passage The Shofar – An Alarm Clock, which describes the way the sounds of the shofar awaken us to soul-searching. 
  • Look at Rodin’s sculpture The Thinker, which depicts a man deep in thought. What body language do we use when we are engaged in soul-searching?  
  • Read the poem I Walk Down the Street by Portia Nelson, which discusses the automatic nature of our actions and suggests a way to make changes in our lives.