Al Capone Does My Shirts
By Gennifer Choldenko.
Puffin Books, 2004.
A Newbery Honor Book.
An ALA Best Book for Young Adults
Many other awards
Concept Analysis
Summary
Moose, a twelve-year old boy, moves with his parents and
sister to Alcatraz Island in 1935 when his dad gets a job as an electrician and prison
guard. Moose is a nickname for Matthew, given him by his sister because he is tall. His
sister, Natalie, has a disability, a form of autism. The mom tells everyone Natalie is ten
(readers find out later that she is actually sixteen.) Moose deals with taking care of his
sister, adjusting to life on the prison island, and the schemes of the Warden’s daughter
Piper. On Alcatraz, he and Natalie become friends with
some of the other kids on the island. Piper, the warden’s
daughter, involves the kids with selling prisoner laundry
service to the other students at their school. Later, Moose
searches for a baseball that the convicts used to give his
best friend, Scout. An overarching plot involves Moose and
his parents try to get Natalie into a school, the Ester P.
Marinoff school for students with disabilities. When she is
repeatedly rejected and there seems no other option,
Moose appeals to Al Capone for help. Suddenly, Natalie is
invited to come to a new school for older students with disabilities.
Organization
Containing 215 pages divided into three parts and forty, titled chapters, Al Capone
Does My Shirts is historical fiction. The titles are creative and give insight into the
events contained in the chapter. A map, using an actual picture of Alcatraz Island and
showing where the characters live and play on the island, occurs at the first of the book.
Organized chronologically, Al Capone Does My Shirts begins in January 1935 and ends
in June of the same year. The book is arranged into three different sections. The first
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section deals with Moose settling in at Alcatraz and Piper’s laundry scheme. In the
second section, the kids on the island arrange to meet Al Capone’s mother and Moose
searches for a convict baseball to give to Scout. Natalie also meets a convict while
Moose searches for the baseball. The third section details what Moose does to get
Natalie into the Esther P. Marinoff School.
At the end of the book, Gennifer Choldenko writes about her research into the
history of Alcatraz and a little about autism. She also details ways in which she stayed
true to the history of the island and ways in which she changed things to accommodate
the story. This book would be best for seventh grade students as there are some more
mature moments that younger kids might not understand—Natalie is nude and Moose
has to get her to put on a dress and Natalie and a convict are together for a while and
there is a hint that something improper may have happened.
Essential Questions
What will I do to achieve my goals?
Moose and his family work hard to get his sister ready and accepted into the Ether P.
Marinoff school. Moving to Alcatraz Island where his dad works as an electrician and
guard so they have money to send Natalie to a new school is just the latest attempt
Moose’s mom makes to help Natalie overcome her disability. The book details many
attempted solutions. When the school rejects Natalie, Moose appeals to the Warden
and Al Capone for help. As Moose puts it, “When you love someone, you have to try
things even if they don’t make sense to anyone else” (201). Moose breaks rules so he
can get his sister help. Additionally, Moose wants a convict baseball for his friend Scout
and searches for hours and hours on many days to obtain a ball. Young teens can
discuss what their goals are and what they are willing to do to achieve them.
What is courage?
The final assessment deals with the definition of courage. As Moose and his family work
to achieve their goals, it takes a lot of courage. They move to a different area. They use
talents to earn more money—Moose’s mom begins to teach piano lessons. Moose
especially shows courage as he stands up for what he believes is best for Natalie and
his parents and resists Piper’s laundry scheme. Additionally, Moose shows courage as
he asks the Warden for help, as he stands up to his mom over Natalie’s age, and as he
appeals to Al Capone for help. Discussing courage will help students see that courage
is needed in daily life, not just in wars or as part of a natural disaster.
What does it mean to be a member of a family?
Moose loves his previous neighborhood. He moves to Alcatraz because his family
needs more money to send his sister to a special school that will help her learn to
function in society, despite her disability. His dad works two jobs and his mom begins
teaching piano lessons. Due to these issues, Moose is expected to watch over his
sister. He is frustrated, sometimes, at all he must give up, but his love of his sister and
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family is real. Students can relate to the pressures Moose feels as his gives up things
for his sister. Are there things students give up to help their family?
QUOTE: “We need the money, Moose. If I get students, I have to take them. . . . Can’t
you play baseball here?”
“Can’t someone else watch Natalie?”
“And pay for a baby-sitter? Even if we did have the money, how would we find
someone who could handle her? We all have to help out, Moose. That’s the only way
this is going to work.” (104)
How do you deal with peer pressure?
Piper wants to earn money by selling the prisoner laundry service available to all the
families who live on the island. She pressures the other kids to help her sneak the
clothes into the laundry. The kids at school give her the clothes they are currently
wearing so she can wash them for this “one time only” event. Moose resists the
pressure to participate, although he does help Piper carry some laundry. Students can
discuss how they respond to peer pressure.
“All right. Let’s ask your dad if it’s okay,” I say.
“Do you ask permission to put on your underwear every morning?”
“I’m just pointing out.”
“I know exactly what you’re pointing out. But no one here sticks to those stupid
rules. You’re the only one, Moose Flanagan.” (73)
What criteria do you use to judge someone?
Moose is required to evaluate people. All teens face this each day. Students can do an
extended definition on judging others. What makes you good or bad? Is there good and
bad in everyone? Is murderer Al Capone good because he helps Moose or bad
because he has killed many people? Is the Warden good because he does not bend the
rules for Moose or bad because he refuses to help?
(Warden) “You can never trust a con. Nobody came here for singing too loud in church.
Do you know what the word conniving means?”
“Sneaky, tricky,” I say.
“That’s right. Remember that, Mr. Flanagan. Conniving mean with no sense of
right and wrong.” (39)
Students can also discuss who is conniving in this book—Piper? Moose? The Warden?
Helen Flanagan? These questions will help students compare the different characters
and find ways to understand why they acted the way they did and how we would judge
their actions.
Background Knowledge
Students will need some knowledge of Al Capone, Machine Gun Kelly, and other
criminals from the 1930s. Understanding the geographical location of Alcatraz and its
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purpose in housing the worst criminals will be important in understanding the book.
Knowledge about the hierarchy of the workers, especially guards and wardens, will help
students understand the Moose/Piper dynamic.
Students will also benefit from a study of autism and the some characteristics of
individuals with autism—obsessive mannerisms, occasional amazing abilities (math in
Natalie’s case), and an inability to emotionally relate to other people. Students should
know the difference between the current ideas of mainstreaming students with
disabilities and the 1930s version of special, private schools or treatment homes or
asylums. Be sensitive to any students in the class who have autism or siblings with
autism.
Issues in this Book
Themes:
Prejudice is a repeated theme in the book. It is explored in Piper and others reactions to
Natalie and her disability. Mrs. Flanagan tells everyone Natalie, who is sixteen, is tenyears-old because, according the Mrs. Kelly, “There is a real bias again older children”
(200). Mrs. Capone, Al Capone’s mother, provides another way to explore this topic.
Another theme is family responsibility. Moose is given the responsibility to watch Natalie
after school. He has to give up playing baseball with friends from school so he can be
home while his mom teaches piano.
Issues of fairness also threads through the story. Moose refuses to participate in Piper’s
scheme since he believes it is breaking the rules. Yet he is equally blamed when the
scheme is discovered.
“Do you have anything to say for yourself? Moose?”
“Sir, I didn’t do anything. That’s what I’ve been trying—“
“NO EXCUSES!” the warden roars so loud, even Natalie looks up. (115)
Fairness also plays a part in his relationship with his mother.
“’I got one child who has everything,’ my mom says, ‘big strapping, healthy, smart
. . . makes people laugh. Got kids coming over looking for him night and day, just like at
home. But Natalie, Natalie doesn’t have the whole world looking out for her. She needs
me’” (175). Students can explore what fairness is and if life is fair.
Setting:
Alcatraz, San Francisco 1935. Alcatraz got its name when, in 1775, “Spanish sailors
first sailed into San Francisco Bay and called the island ‘La Isla de los Alcatraces,
Island of the Pelicans, after the birds that covered the “Rock’“ (Murphy 9). In 1854, a
lighthouse was build to guide ships into the harbor. Later, in 1853, Alcatraz was home to
a post of the U.S. Army, built to “protect the city of San Francisco from invasion by sea”
(13). By the early 1900s, the army changed the island from fort to military prison. Later,
in August of 1934, the island became the a prison for the worst prisoners, “the worst of
the worst” (Choldenko 3) is how Moose puts it. It had tough, modern defenses and was
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not connected by road to any land. The only safe way on or off the island was by boat.
Due to deteriorating conditions of the prison and high maintance costs, Alcatraz closed
its prison in 1963 (see Alcatrazhistory.com).
Point of View:
First person. The story is told from Moose’s point of view.
Characters
Michael “Moose” Flanagan: Nicknamed Moose by his sister, the story is told in first
person from his perspective. He loves baseball. As Natalie’s only sibling, he has the
responsibility for taking care of her after school. He attends school in San Francisco
with Piper.
QUOTE: “I want to be here like I want poison oak on my private parts. But apparently
nobody cares, because now I’m Moose Flanagan, Alcatraz Island Boy—all so my sister
can go to the Esther P. Marinoff School, where kids have macaroni salad in their hair
and wear their clothes inside out and there isn’t a chalkboard or a book in sight” (3-4).
Natalie Flanagan: Moose’s sister. At the beginning, readers find out that Natalie’s mom
tells everyone she is ten and has been ten for years. Natalie likes to play with buttons
and has impressive math and memory skills. She sometimes has problems when her
routine is different. Her parents are trying to get her into a school, the Esther P. Marinoff
school, that helps students with disabilities.
QUOTE: (Natalie) “Moose and Natalie go on a train. Moose and Natalie eat meat loaf
sandwich. Moose and Natalie look out the window.”
(Moose) “Yeah, we did all that. And now we’re here with some swell fellows like Al
Capone and Machine Gun Kelly.”
(Natalie) “Natalie Flanagan’s whole family.” (4)
Piper Williams: The warden’s daughter who is always coming up with schemes. She is
the same age as Moose and they attend school together.
QUOTE: She rubs her hands together. “We’re in business. All you need to do is talk
about Alcatraz. Get people in the right mood. You’ll talk up the place, kind of like the
warm-up, and I’ll tell a few people, then let the word spread. You must know some
amazing stories,” she says as the boat motor grinds beneath our feet.
Theresa Mattaman: Another girl who lives on the island. She has cards on the famous
convicts on the island with basic information. She is seven years old and shows Moose
and Natalie around the island. She and Natalie become friends.
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Theresa claps her hands, then digs in her pocket for a card folded in fours. “I made this
for you. Annie did the words. I made the map all by myself!”
Cam Flanagan: Moose and Natalie’s dad. He is a guard and electrician at Alcatraz. He
works a lot and doesn’t have much time for Moose. He is the parent Moose can talk to
about problems with Natalie.
QUOTE: My dad sighs. He looks out at the water to where they’re building the Bay
Bridge—two toothpicks held together by a thread of steel. He’s quiet for a long time.
“Nobody knows how things will turn out, that’s why they go ahead and play the game,
Moose. You give it your all and sometimes amazing things happen, but it’s hardly ever
what you expect” (33-34)
Helen Flanagan: Moose and Natalie’s mother. She teaches piano after school in San
Francisco and is always trying new things and off-the-wall ideas to help Natalie. She lies
about Natalie’s age and doesn’t seem to be emotionally connected to her children.
QUOTE: “What’s the matter?” I ask Natalie.
“She’s fine,” my mother answers for her. “We’ve been all over. We’ve had a lovely day.”
My mom glances quickly at me and then looks away.
“She looks upset.”
“It’s just hot, that’s all.” My mom rubs her neck.
“She wants her buttons.”
“Well . . . yes . . . ,” my mom admits. “But I’m sure once you take her out, she’ll forget all
about it. Mrs. Kelly says it’s just a matter of redirecting her attention.” My mom’s voice
isn’t quite so sure as her words are. She and Natalie have clearly had a hard time
today. (90-91)
Minor Characters
Al Capone: A prisoner on Alcatraz for tax evasion. He was a mob boss in Chicago.
Onion: Prisoner 105. Natalie meets him and they become friends.
Annie Bomini: Another child on Alcatraz Island. She helps Piper with her schemes and
plays baseball with Moose.
Miss Bimp: Moose and Piper’s teacher in San Francisco.
Scout McIlvey: Moose’s friend. He plays baseball and wants a baseball used by the
convicts.
Jimmy Mattaman: Lives on Alcatraz. Brother to Theresa. Doesn’t play baseball.
Bea Trixle: Another adult who lives on Alcatraz. She gives perms in her apartment and
answers the apartment phone.
Mrs. Kelly: Natalie’s teacher. She suggests taking away Natalie’s buttons. Natalie
improves after working with her.
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Literary Terms
This book is helpful in teaching the Common Core requirement of story elements—
rising action, climax, falling action. It can also be used to Compare and contrast a
fictional portrayal of a time, place, or character and a historical account of the same
period as a means of understanding how authors of fiction use or alter history. Other
teaching options include:
Foil—Piper and Moose are set up as foils for each other. Both of their dads work at the
prison, both attend school together in San Francisco. They approach life on the island
very differently. Piper is the Warden’s daughter, but always breaks the rules. Moose is a
guard’s son, but wants to keep the rules. Their approach to Natalie is also very different.
How might the story be different if Piper told it?
Voice—Moose has a very strong voice. The story is told from his perspective. His
conflicts between wanting to help his family and wanting to be a student with no
responsibilities are relatable for students. Students can analyze why voice is important
in this story and ways they hear his voice in the writing.
Conflict—The story contains man-against-self conflicts when Moose struggles in his
desires to help Natalie and his desires to be free to play without watching her every day
after school. Moose struggling to fit in at a new school and on the island at Alcatraz is
something students can understand. There are also man-against-man struggles as
Moose and Piper interact and Moose resists Piper’s rule-breaking schemes. Or in the
family’s desire to have Natalie accepted into the Esther P. Marinoff School.
Inferences—Al Capone’s mother comes to visit the island. She doesn’t speak English.
Moose infers that from her reactions when they meet on the boat. When the kids
interact with her, they use inferences to understand what happens to her at the snitch
box. These stories can be used to teach students inferences.
Affective Issues
Moose is in seventh grade, the same as the target audience. Students will relate to his
desire to play baseball, his struggle to make friends, and his obligations and chores at
home. Moose moves to a new area and needs to make friends and deal with the long
hours his dad works.
He deals with making new friends: “There’s nothing like a double play to make yourself
a friend or two” (52). How have common interests helped them make friends. What are
other ways they found to make new friends?
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Moose loses his only friend, “I head for the library and eat by myself. Scout’s the only
real friend I’ve made so far and apparently I’ve lost him already” (109). Students can
write about losing a friendship and how they healed the friendship.
Moose gets blamed for something he didn’t do:
“Do you have anything to say for yourself? Moose?”
“Sir, I didn’t do anything. That’s what I’ve been trying—“
“NO EXCUSES!” the warden roars so loud, even Natalie looks up. (115)
Students can write about a time when they were blamed for something they didn’t do.
This will help students relate to Moose.
Helen Flanagan is always trying different things to help Natalie; sometimes these things
are bazaar. Moose eventually does as well. It is all summed up in this quote:
“When you love someone, you have to try things even if they don’t make sense to
anyone else” (201). Students can think about what try to do when a family member
needs help.
Moose’s dad works two jobs. He misses doing things with him.
“Dad! Could you show me the cell house, and then maybe could we play ball?” I
sound like I’m six and a half now, but I can’t help it. He’s been gone forever and I
hardly got to see him at all yesterday. It’s lonely in my family when he’s not
around. (7)
Students can discuss how parent choices impact their lives and influence what activities
they can or cannot do.
Vocabulary Issues
Al Capone Does My Shirts is a relatively easy book to read. There are a few words from
the 1930s that are used that students might need to understanding. Idioms used in the
book should be taught to students. Here are some examples:
Nutty as a fruitcake (87)
Taking someone to the cleaners (102)
Setting a precedent (203)
Saving face (208)
Heinous (37)
Wallop (51)
Asylum (66)
Replicate (67)
Skirmish (68)
Shiv (75)
Icebox (104)
Snitch box (134)
Preferential treatment (203)
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Implications for Students of Diversity
There are different ethnicities represented, all in a positive light. Mrs. Capone doesn’t
speak English and raised a murderer, but comforts Rocky, the Mataman baby. “Mrs.
Capone takes Rocky in her arms and rocks him gentle and wide like a large cradle.
Almost immediately, as if by some spell, Rocky stops crying. Mrs. Capone keeps
rocking, her smile broad and sweet” (133). Students can explore how they thought Mrs.
Capone would be tough, like her son, but is, instead, soft and sweet, like a grandma.
Additionally, addressing the fact that Mrs. Capone does not speak English might open
the subject of the value of learning English when you live in America. Since she gets
help from another mom on the island, teachers can aid students in understanding the
value of learning more than one language.
Because Natalie has a disability, Piper asks, “She retarded?” When told no, she says
“So, not retarded. Stupid, then?” Piper asks (17). Students need to understand that
“retarded” is a very negative term, but was not as bad in the 1930s when people didn’t
know as much about Autism as we do now. Help students, especially those with
disabilities, see that people who learn slower are not stupid and deserve respect. Also,
in the story, Moose describes his ideas of the type of school Natalie will attend. “. . . all
so my sister can go to the Esther P. Marinoff School, where kids have macaroni salad in
their hair and wear their clothes inside out and there isn’t a chalkboard or a book in
sight. Not that I’ve ever been to the Esther P. Marinoff. But all of Natalie’s schools are
like this” (4). Teachers need to address the fact that students with disabilities were not
mainstreamed into “normal” schools and were not taught skills at these schools, just
physically taken care of. See “A Brief History of the Disability Rights Movement” at
www.adl.org for history of the treatment of people with disabilities and “Special
Education at www.encyclopedia.com for more history on educating students with
disabilities.
Gender Issues
Moose’s parents have traditional roles—his dad works, his mom teaches piano. It was
not until World Ward II that married women worked outside the home. Teaching piano
or school, as one of the moms does for the younger students, like Theresa, were some
of the only acceptable ways for women to earn money. You might address that women
in the 1930s didn’t work as prison guards at male prisons at this time and gender roles
were more rigidly defined—fathers worked and mothers cared for children.
Moose assumes a girl can’t play baseball. He states, “I run up close. I don’t want to
embarrass her. She’s only a girl, after all. I pop her one light and easy.”
“She catches it no problem and zips me a hard fastball.” (56)
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Research Issues/ Project Ideas
Students can conduct inquiry on the history of Alcatraz. What was it first used for and
what is the present day use of this island? Where did it get any nicknames? Citing text
in the book, students can then show where facts about Alcatraz are used in a fictional
narrative. This activity can be used to teach citation of sources, inquiry, and using facts
as a part of good narrative writing.
Al Capone Does My Shirts is written as a series of daily, first person journal-like entries.
Students can write a story using the epistolary format. Alternatively, students could keep
a journal of what happened in their lives for two weeks about their school or home
experiences.
Students can design a poster advertising the laundry service of Piper’s. They could also
create another possible service the kids could sell to their friends at school and create a
poster advertising that service, a price for the service, and detail how they would carry
out the plan.
The author uses Moose’s perspective to tell the story of life on Alcatraz. Students can
rewrite a chapter, page, or a story (meeting Mrs. Capone or selling laundry) from a
different point of view (Piper, Natalie, Scout). This activity will help students understand
the importance of point of view and how a story changes when a different character tells
it. (Reading anchor standard 6)
Moose has to move from his comfortable neighborhood and start over in the middle of
seventh grade. Have students think about places they could move to that would be very
different—maybe another country or part of this country. Conduct inquiry about that
place researching the type of schools or school systems, transportation to the school,
clothes the students wear (are there uniforms?), and other issues related to moving to
that area. Students could write a narrative, imagining they or a fictional character move
there and must adjust to the new area.
Al Capone Does My Shirts has a sequel—Al Capone Shines My Shoes. In that story, Al
Capone wants a favor from Moose. Have students create a short story describing the
favor Al Capone wants and if Moose does it or not.
Text Sets and Enrichment Resources
Children of Alcatraz: Growing up on the Rock by Claire Rudolf Murphy
This book is a good resource on what it was like to live on Alcatraz. It includes
plenty of pictures and some tales of what it was like to live on Alcatraz. Pictures of the
cell blocks and past criminals are also included. The book details the history of Alcatraz
and the different purposes it served.
Alcatraz: The Gangster Years by David Ward with a contribution by Gene Kassebaum.
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Students can use this book to learn more about the criminals housed in Alcatraz
during the time the story takes place. It also includes information about the lives of the
guards.
Alcatraz: Prison for America’s Most Wanted by C.J. Henderson.
This book, which includes pictures and profiles of the criminals housed there, can
serve to build background knowledge on Alcatraz and its prisoners. Students read parts
of the book and answer questions to help them understand where the story takes place
and information about the criminals housed at Alcatraz.
Rules by Cynthia Lord
Rules is another book involving a character with a disability. Told from the
perspective of a twelve-year-old girl with an autistic brother, students can explore
reactions to students with disabilities. It takes place in a modern setting, with current
technology, so exploring how things have changed is a possible option. Catherine, the
protagonist, befriends a student who can’t speak and learns to accept others who are
different. It can function as a paired text.
The Curious Incident of a Dog in the Night-time by Mark Haddon
This book is told with the voice of an autistic older teen. It should only be used in
snippets or with caution as the language and issues are geared more toward older
students. However, students could listen to a page or two (carefully selected for content
and language) read by the teacher and discuss how the protagonist understands things
differently—what rules help him deal with his life and how might they understand things
differently in the same situation.
AlcatrazHistory.com
This website includes FAQs about Alcatraz, articles about its history, biographies
about famous residents, a map (very similar to the one in Al Capone Does My Shirts) of
the prison, photos and much more to aid in student research projects.
HistoryChannel.com: “Al Capone” and “Alcatraz”
“The Many Moods of Al Capone” is a short video (2:38) detailing some of the
interests of Al Capone. He was a vicious criminal, but opened soup kitchens for poor
people. Preview all of the videos, as there is also a mention of Al Capone’s insanity due
to syphilis.
“Alcatraz Deconstructed” is a short (2:35) video about the physical characteristics and
history of Alcatraz.
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Works Cited
Alcatrazhistory.com. Ocean View Publishing Company. 2011. Web. 10 November 2012.
Murphy, Claire Rudolf. Children of Alcatraz: Growing Up on the Rock. New York: Walker
& Company, 2006. Print.
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