Al Capone Does My Shirts
by Gennifer Choldenko

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. 

Gennifer Choldenko was born in Santa Monica, California, in 1957, the youngest child in a family of four children. One of Choldenko's sisters suffered from severe autism and inspired the character of Natalie in this book. Choldenko began her writing career with a job as a copywriter in a small ad agency. She began taking classes in illustration, and this eventually led to a full-time study of illustration at the Rhode Island School of Design. After becoming very successful in advertising, she began to pursue her real love children's books, and her first novel Notes from a Liar and Her Dog was chosen as a School Library Journal Best Book of  the Year and won several other awards. Choldenko is married with two children, and she lives in the San Francisco Bay area.

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? 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?