Al Capone Does My Shirts

Use these essay questions as writing and critical thinking exercises for all levels of writers, and to build their literary analysis skills by requiring textual references throughout the essay.

Differentiation Suggestion: For English learners or struggling writers, strategies that work well include graphic organizers, sentence frames or starters, group work, or oral responses.

Scaffolded Essay Questions

Student Prompt: Write a short (1-3 paragraph) response using one of the bulleted outlines below. Cite details from the text over the course of your response that serve as examples and support.

1. Alcatraz is described negatively by Moose at first, who claims it is a “rock covered by cement topped with a bird turd and surrounded by water.” (Chapter 1)

• How is the setting of Alcatraz Island developed as a character in the novel? (topic sentence)
• Explain how the history of the island, the visual appeal of the island, and the isolation of the island all contribute to Alcatraz as its own character in the novel.
• In your concluding sentence or sentences, describe how the author contributes to the island’s character through her descriptions.

2. Piper is often depicted as selfish and unfeeling toward other characters.

• What is Piper’s role in the novel? (topic sentence)
• Explain how Piper influences Moose’s behavior and contributes to his character development. Describe how Moose influences Piper’s behavior.
• In your concluding sentence or sentences, explain whether you believe Moose should be friends with Piper or not and why.

3. The initial impression of the inmates on the island given in the novel is that they are manipulative and cruel.

• How do the prisoners on Alcatraz Island defy people’s expectations of them? (topic sentence)
• Explain how the perception of the prisoners changes after certain events in the novel. Explain each event and what the situation or outcome shows about the prisoners.
• In your concluding sentence or sentences, explain how these changes to prisoner expectations are related to the novel’s theme of The Importance of Empathy and Understanding.

Full Essay Assignments

Student Prompt: Write a structured and well-developed essay. Include a thesis statement, at least three main points supported by text details, and a conclusion.

1. Natalie does not speak often with the characters in the novel, but she has a significant impact on those around her. How does the author show readers Natalie’s impact on others? What lesson is Natalie able to teach her family and friends? To what extent and in what ways do the characters change their perspectives because of Natalie? Select events that support your ideas to discuss in your essay.

2. Mrs. Carrie Kelly tells Helen Flanagan that “[they] can’t let [themselves] get in Natalie’s way […] [They’re] the stumbling block. If Natalie is going to change, [they] have to change first.” (Chapter 13) Think about the concept of change in the novel. How were Helen and Cam a “stumbling block” to Natalie’s growth? How might Moose have been a “stumbling block” for Natalie? What did the characters do that ultimately allowed Natalie to change? Considering this, do you think Natalie’s family made the right decision to send her away to school? Support your evaluation with plot and character details.

3. Each new friend Moose makes on Alcatraz Island has specific traits. How does Moose grow as a result of his new friends and acquaintances? What qualities does each friend encourage in Moose? Why might the author have used friends as a catalyst for Moose’s character growth?