Al Capone Does My Shirts

   Al Capone Does My Shirts by Gennifer Choldenko

Today I moved to a twelve-acre rock covered with cement, topped with bird turd and surrounded by water. I'm not the only kid who lives here. There's my sister, Natalie, except she doesn't count. And there are twenty-three other kids who live on the island because their dads work as guards or cook's or doctors or electricians for the prison, like my dad does. Plus, there are a ton of murderers, rapists, hit men, con men, stickup men, embezzlers, connivers, burglars, kidnappers and maybe even an innocent man or two, though I doubt it. The convicts we have are the kind other prisons don't want. I never knew prisons could be picky, but I guess they can. You get to Alcatraz by being the worst of the worst. Unless you're me. I came here because my mother said I had to.

Discussion Questions

  1. During his first night on Alcatraz Island, how does Moose Flanagan sleep?
  2. Who is “105,” and why does this person cause Moose so much anxiety?
  3. What is Piper like? Moose finds himself both attracted to Piper and very suspicious of her. If you could, give Moose some advice about how to handle Piper, what would you say? How do you think Moose ought to respond to her?
  4. What is it about Natalie’s behavior that makes it difficult for her family to live with her?
  5. Why do you think it is so important to Mrs. Flanagan to keep celebrating Natalie’s tenth birthday? And how does Moose get her to change her mind about this?
  6. Imagine that like Moose you had a sibling who lived with a significant disability or condition like autism. How would your life be different? Do you think you would relate to your sibling like Moose relates to Natalie?
  7. As Moose obediently helps his sister off the boat as they head to school, he thinks to himself, “Good Moose, obedient Moose. I always do what I’m supposed to do” (p. 28). Is this true?
  8. Mrs. Flanagan tells Moose: “You’re better with Natalie than I am.” (p. 180) What does Moose do for Natalie that their mother does not? How does Moose treat Natalie? And how do Moose’s friends on Alcatraz play a role in helping Natalie?
  9. From the beginning to the end of the novel, which characters seem to show signs of changing? How do they change? Do you think these changes will last?
  10. How did Natalie really get accepted to school? What made Mr. Purdy suddenly decide to open another school? Did Moose’s letter to Al Capone make a difference?
  11. Imagine the Flanagan family after Natalie has left to attend Mr. Purdy’s new school. How will Moose’s life change when Natalie is away at school? Will his relationship with his parents be different with Natalie out of the house?
  12. Is Mrs. Flanagan a good mother to Moose? Is she a good mother to Natalie? Why does she treat her children so differently? Is she right in being this way?
  13. Based on the title of the book, what did you think this book would be about before you read it? How was the story different from what you originally expected?
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