Last updated: July 16, 2026
Written by Gennifer Choldenko, Al Capone Does My Shirts is a captivating and engaging historical fiction novel. It will transport readers back in time to the infamous Alcatraz Island during the 1930s.
Reading Level
Lexile 600L
Interest Level
Grades 6-8
Length
241 pages
Award
Newbery Honor
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⭐ About the Book: Al Capone Does My Shirts
Al Capone Does My Shirts by Gennifer Choldenko is a compelling historical fiction novel set on Alcatraz Island in 1935. Twelve‑year‑old Moose Flanagan has just moved to the island after his father accepts a job as a prison guard. Life on “the Rock” is nothing like Moose expected — the island is isolated, the rules are strict, and the presence of notorious criminals looms over everything.
Moose struggles to adjust to his new home while also helping care for his older sister, Natalie, who is on the autism spectrum. School challenges, social pressures, and family responsibilities weigh heavily on him. When Moose unexpectedly forms a connection with Al Capone — yes, that Al Capone — his world becomes even more complicated. Capone’s influence brings both excitement and trouble, forcing Moose to confront difficult choices about loyalty, responsibility, and what it means to stand up for the people you love.
This Newbery Honor novel is rich with humor, heart, and historical detail. It’s an excellent choice for teaching character development, historical context, point of view, and themes related to family, neurodiversity, and growing up.
⭐ Book Details
| Publication Date | April 20, 2006 |
| Reading Level | Lexile 600L • Guided Reading Level X |
| Interest Level | Grades 6–8 |
| Awards | Newbery Honor • California Young Reader Medal |
| Length | 241 pages |
| Estimated Word Count | Approx. 53,505 words |
| Audiobook Length | 6 hours and 10 minutes |
| Genre | Historical fiction (young adult) |
| Setting | Alcatraz Island near San Francisco, 1935 |
| Themes | Coming of Age, Brothers and Sisters, Friendship, History, Autism |
| Point of View | First-person (Moose Flanagan’s journal-style narration) |
| Memorable Quote | “Nobody knows how things will turn out, that’s why they go ahead and play the game… You give it your all and sometimes amazing things happen, but it’s hardly ever what you expect.” |
| First Line | “Today I moved to a twelve-acre rock covered with cement, topped with bird turd and surrounded by water.” |
Al Capone Does My Shirts Activities
Book Unit Samples
You will find the following in this novel study sample:
- Vocabulary Practice for Chapters 1-2
- Comprehension Questions for Chapters 1-2
- Constructed Response Question – Setting
Teaching Idea #1 – Bump Games
These two Bump Games cover important reading skills: using context clues and figurative language. The sentences used to practice these skills are lines from the novel. Both full color and black-lined versions are provided in this print-and-go activity. Use games in small groups for a fun interactive activity.
Teaching Idea #2 – Activities on the Web
Gennifer Choldendo Website – Learn about the other books in this series at Gennifer Cholodenko’s website.
ReadWriteThink has a lesson plan on Travel Brochures featuring Al Capone Does My Shirts.
Teaching Idea #3 – Alcatraz Island
Have students research Alcatraz Island, the setting of the novel, and its history as a prison. They can create posters, timelines, or virtual tours of the island to share with the class.
Teaching Idea #4 – Bullying
How does Piper use her power to bully others? Why do you think she behaves this way?
How does Moose’s sister Natalie experience bullying in the novel? What impact does it have on her and her family?
How does Moose respond to being bullied by Jimmy? What are the consequences of his actions?
Teaching Idea #5 – Symbolism
Alcatraz Island:
Alcatraz represents the challenges that Moose and his family face.
The Laundry:
Moose’s mother does the laundry. This way to make money symbolizes hope and betterment.
The Baseball:
Baseball is a symbol of unity and friendship. It brings Moose and the other boys on the island together.
The Box of Buttons:
The buttons symbolize the unique qualities of each person and the importance of recognizing and valuing those qualities.
Teaching Idea #6 – The Series
After reading Al Capone Does my Shirts, be sure to introduce students to its sequels.
- 2011 – Al Capone Shines My Shoes
- 2014 – Al Capone Does My Homework
- 2018 – Al Capone Throws Me a Curve
Each book in the series features Moose Flanagan and his sister Natalie. All books in the story take place on Alcatraz Island in the 1930s where the siblings meet notorious criminals.
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Al Capone Does My Shirts Novel Study includes vocabulary practice, comprehension questions, constructed response writing, and skill practice.
