Tom Walker’s Story as a Moral Allegory: “The Devil and Tom Walker” is a moral allegory, a story that reveals a moral or message. Washington Irving uses its main character, Tom Walker, to instruct readers about hypocrisy, greed, and the corruption that wealth and power bring.

• For discussion: What is the moral of the story? How do Tom and his wife help reveal the moral? What are their actions, and what are the consequences of their actions?
• For discussion: What does Tom claim right before he is taken by the devil? What does this statement reveal about Tom’s nature?
• For discussion: How does the narrator end the story? What moral can be found there?

Irving’s Use of Symbolism: Irving uses symbols to highlight the story’s moral. Symbols of importance within the story include the shortcut through the swamp, the trees in the swamp, and fire.

• For discussion: How might symbols serve a story better than stating ideas outright? What does Irving’s use of symbols contribute to the tone and themes of his story?
• For discussion: What do the trees in the swamp symbolize? How do the details of the trees in the swamp correspond to the people they symbolize? What happens when the devil cuts down a tree?
• For discussion: Find each instance of fire symbolism within the story. How does it contribute to the story’s moral?
• For discussion: In the beginning of the story, Tom takes a shortcut. What does this shortcut tell you about Tom’s nature? How does the narrator describe shortcuts? What could a shortcut symbolize?
• For discussion: What other symbols recur throughout “The Devil and Tom Walker”? What functions might they serve?

“The Devil and Tom Walker” as a Social Commentary: In “The Devil and Tom Walker,” Irving addresses several social issues of his time. Through fiction, Irving comments on the immorality of the slave trade, the greed and corruption of those in power, and religious persecution and hypocrisy.

• For discussion: What social commentary does Irving make about the slave trade? How does he weave this commentary into the story?
• For discussion: What does Tom do with his newfound wealth and power, and how do his actions reflect his greed? What does this suggest about wealth and power in society?
• For discussion: In “The Devil and Tom Walker,” the devil supports the persecution of Quakers and Anabaptists by other Christians. What does the devil’s support say about religious persecution? What is the irony implied behind Christians persecuting other Christians?

Tom’s Story as a Faustian Legend: Tom Walker’s decision to sell his soul to the devil is reminiscent of the German legend of Faust. In the legend, Faust sells his soul for knowledge and power, much as Tom sells his soul for monetary gain. In many versions of the legend, Faust is eventually taken by the devil due to his irrevocable moral corruption—a fate identical to that of Tom Walker.

• For discussion: How is Tom’s character first described? What is Tom willing to sell his soul for? What other stories have a character making a “deal with the devil”?
• For discussion: What does Tom begin to fear as he becomes older? How do his efforts to protect his soul from the devil show hypocrisy and moral corruption?
• For discussion: Tom is taken by the devil at the end of the story. What does this say about making a deal with the devil? Do you think Tom’s fate was inevitable?

Additional Discussion Questions:

• The devil introduces himself using several names or titles. What ideologies or actions do these names and titles suggest the devil supports?
• The devil is described as wearing Native American garb, and is the “Evil Spirit” that the Native Americans communed with in the swamp. Why do you think Irving chose to describe the devil in this way? What does this say about American society in the 18th and 19th centuries?

Tricky Issues to Address While Teaching

The Story Includes Racist Beliefs and Language: The presence of the devil in the swamps outside the Boston colony is directly attributed to Native Americans. Specifically, they are described as having “consecrated” their fort to the devil through human sacrifice. On a diction level, Irving’s language contains terms and phrases that can be read as racist, given their context. For example, the narrative frequently refers to the devil as “the black man.” While it is made clear this is not a reference to race—“the stranger was neither negro nor Indian”—the repeated use of that phrase in attachment to an embodiment of spiritual evil could be jarring and uncomfortable for students.

• What to do: Remind students of the specific tropes of the gothic genre, such as isolated and creepy settings, death, and the supernatural. Irving uses the colonists’ lack of understanding of Native Americans to create the mystery needed for the gothic mood of his narrative. For Irving's 19th-century readership, the use of Native American stereotypes for fictional effect may well have been considered customary, despite the obvious falsehood of those stereotypes.
• What to do: Situate “The Devil and Tom Walker” within the folkloric tradition that Irving wished to build for the United States. Discuss with students the characteristics of regionalism, and remind them that Irving was writing stories he hoped would emulate the tone of an oral tradition. Though he was publishing in the 1820s, in setting his stories a hundred years before, Irving repeated beliefs and viewpoints that he himself may not have held.
• What to do: More advanced students can be introduced to some of Irving’s other writing about Native Americans, such as “Traits of Indian Character” from The Sketch Book of Geoffrey Crayon, Gent. Critical examination of his works can serve as an opportunity to address the changes in beliefs about and treatment of Native Americans between the colonial period and Irving’s lifetime, and between Irving’s lifetime and the present.

Tom sells his soul to the devil: “The Devil and Tom Walker” makes several references to the devil, damnation, hell, and the selling of one’s soul. These topics may cause discomfort for some students.

• What to do: View the characters of the devil, Tom, and Tom’s wife as the embodiment of moral corruption. The short story acts as a moral allegory, meaning that Tom Walker and the devil are characters whose actions reveal a moral lesson. Invite students to critically analyze Tom, Tom’s wife, and the devil to see how they exhibit moral failings—and the consequences of those failings.

Tom and his wife have a bad relationship: “The Devil and Tom Walker” depicts both Tom and his wife as meagre, miserly people. They argue over the ownership of everything in their household. Tom’s wife is described as a “termagant,” meaning an ill-tempered and violent woman, and she often mistreats Tom. When Tom’s wife dies, Tom shows no remorse and even sees her death as a source of relief. This may be shocking to some students.

• What to do: View Tom’s relationship with his wife as a satire on the broader institution of marriage. Tom and his wife are exaggerated characters whose actions play into Irving’s satirical take on marriage. Ask students to find and compare aspects of Tom and his wife’s relationship to common negative conceptions about marriage and gender roles.

Alternative Approaches to Teaching "The Devil and Tom Walker"

While the main ideas and discussion questions above are typically the focal points of units involving this text, the following suggestions represent alternative readings that may enrich your students’ experience and understanding of the story.

• Focus on the gothic elements in the story. Irving uses vivid, creepy, and gloomy settings in his short story. Explore with students how these settings contribute to a sense of fear and foreboding.
• Focus on the supernatural aspects of the story. Invite students to analyze how supernatural elements—such as witchcraft, the devil, and superstition—play a role in shaping the story.
• Focus on the fictional sketch genre. “The Devil and Tom Walker” is an example of a genre called “fictional sketch” in which a story is told by a skeptical narrator. This narrator explores other versions of the story, giving readers the impression of being told a legend or fairy tale that has been passed down through generations. Invite students to create their own fictional sketch using a similar structure.