Gennifer says



Visit Al Capone
on Alcatraz

Teaching guide
Global editions

Weird Alcatraz facts

by Gennifer Choldenko
ages 10 and up
G.P. Putnam’s Sons, 2004, ISBN 
0-39923-861-1 (hardcover)
Puffin, 2006, ISBN 
0-14240-370-9 (paperback)

Scholastic Literature Circle Guide made available courtesy of Scholastic Book Clubs.

Use the following questions and activities to get more out of the experience of reading
Al Capone Does My Shirts.

1. During his first night on Alcatraz Island, how does Moose Flanagan sleep?
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?
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?

Note: These literature circle questions are keyed to Bloom’s Taxonomy as follows: Knowledge: 1-3; Comprehension: 4-6; Application: 7-8; Analysis: 9-11; Synthesis: 12-13; Evaluation: 14-15.


1. Research to learn more about Al Capone or another famous criminal mentioned in the novel who spent time at Alcatraz. Draw a timeline to depict the criminal’s life, using drawings and descriptions to show important events.
2. If Moose believes that Al Capone is responsible for Natalie’s admission in the school, how would he thank him? If he wrote a letter to Capone, what would he say? Write a thank-you letter from Moose to Capone.
3. What is autism? Use the Internet or reference books to learn more about autism, and create a poster to help educate your fellow classmates about this disorder. Be ready to explain which signs of autism Natalie displays. Also, how has the treatment of autism changed since the 1930s?

Create a poster advertising Piper’s laundry scheme as described on p. 75. If Piper came up with another money-making venture, what might it be? Would her next plan be as sneaky as the first? In a group, come up with a new idea that Piper might use to make money on Alcatraz Island, and create another poster advertising her new scheme.

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© 2005- Gennifer Choldenko. All rights reserved. If you would like to reuse or reprint anything on this website, please ask the author's permission.