Al Capone Does My Shirts

by: Gennifer Choldenko


Moose Flanagan and his family have just moved to Alcatraz Island so that his father can take a job as a prison guard and his sister Natalie can go to a special school in San Francisco. Moose misses his old baseball team, and he struggles for recognition in his new school.

Then his sister Natalie, who suffers from autism, is rejected from the Esther P. Marinoff School, crushing his parents' hopes for Natalie's education. Now Moose must take care of Natalie after school while his mother teaches music lessons, and he must find a way to deal with Natalie's screaming fits and constant needs.

Complicating Moose's life even more is Piper, the daughter of the prison warden. Piper lures Moose into her scheme to make money by collecting laundry from their classmates with the promise that Al Capone is among the convicts assigned to laundry duty on Alcatraz.

Gradually Moose adjusts to life on Alcatraz, even finding ways to help Natalie fit in with the other children on the island, and he is able to convince his mother that he really does have his sister's best interests in mind. After the Flanagans have tried repeatedly and unsuccessfully to enroll Natalie in the Esther P. Marinoff School, Moose secretly writes a note to Al Capone, asking him to help Natalie. Piper slips Moose's note into the prison's dirty laundry, and a few weeks later, Natalie is accepted to a brand-new school for older autistic children, to the delight of the entire Flanagan family.

Alcatraz: Click on pictures for videos

Chapter 1










Chapter 2








Literacy Circle Questions

1. How does Moose Flanagan sleep during his first night on Alcatraz Island?

2. After Natalie has spent just one night at the Esther P. Marinoff School, Mr. Purdy calls the Flanagans to let them know that Natalie isn’t ready for the school. What reason does he give for sending her back home?

3. Who is “105,” and why does this person cause Moose so much anxiety?

4. Describe Moose’s first contact with Piper Williams, the warden’s daughter. What is Piper like, and how does Moose react to her?

5. What is it about Natalie’s behavior that makes it difficult for her family to live with her? 6. 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?

7. 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?

8. 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?

9. 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?

10. 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?

11. 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?

12. 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? Describe two or three possible scenarios to explain what may have happened.

13. 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?

14. 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?

15. 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?

Journal Entry Questions

Pick one of the following;

  • Were you surprised about what happened today? Predict what you think will happen next?
  • Pretend you are the main character and write in first person a diary entry that he would write. What would you do now?
  • Describe the mood in the chapter and give examples from the book to prove your point.
  • Make a personal connection with the book. What's something in it that reminds you of something in your life? Explain.
  • This story tool place many years ago, how do you think this story would be different if it was about present day?
  • Write a letter to the main character telling them what you think they should do.
  • Change one thing about the chapter you just read and talk about how the story would have been.
  • Add a new character to the book and write about what affect it would have in the story.