Al Capone Does My Shirts

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Al Capone Does My Shirts
Al Capone Does My Shirts cover.JPG
Author Gennifer Choldenko
Country America
Language English


's literature
Set in Alcatraz Island, near San Francisco in 1935
Published Puffin; Reprint edition (April 20, 2006)
Pages 240
Awards Newbery Honor selection, California Young Reader Medal in 2007
Followed by Al Capone Shines My Shoes

Al Capone Does My Shirts is a historical fiction novel for young adults by author Gennifer Choldenko. In this story, Moose Flanagan and his family move from Santa Monica to Alcatraz Island. The move was caused by the father's new job positions as an electrician and as a guard in the well known Alcatraz prison. The book was named as a Newbery Honor selection and in 2007 it received the California Young Reader Medal. It has two sequels, Al Capone Shines My Shoes and Al Capone Does My Homework.[1][2][3]


Moose Flanagan and his family move from Santa Monica to Alcatraz Island in the 1930s. The move was caused by the father's new job positions as an electrician and as a guard in the well known Alcatraz prison. Off the island there is a very prestigious school for children with mental illness to help teens during most of the book, but Mrs. Flanagan tells people that Natalie is ten so that they will not believe she is too old to be helped. Mrs. Flanagan tries applying Natalie to the Esther P. Marinoff School. Mrs. Flanagan believes this is the only way to help "cure" Natalie of her peculiarity and is doing her best to avoid sending Natalie to a mental institution. Due to his parents' hectic work schedule Moose is left with almost full responsibility of his autistic older sister Natalie along with fitting into his new school. Natalie is accepted into the Esther P. Marinoff School, but unfortunately, she's sent back home almost immediately because she's just not adjusting to the school. Moose's mother and Natalie's new psychologist, Mrs. Kelly, push Moose to take full care of Natalie and to take her everywhere he goes to help improve her social skills.

Moose becomes friends with the warden's daughter Piper, who talks him into being part of her money making scheme. One of her schemes is a criminal laundry service for the kids at school. Once the scheme flops and the Warden hears of it, the children are punished and have to find a new hobby. Moose decides to hang around the prisoners' rec center trying to find a stray baseball just to help him fit in with the other kids on the island. Moose eventually notices his older sister Natalie developing a relationship with convict 105, also known as Onion. The convict knows Moose has been looking for a baseball, and he hands Moose a ball just for amusement. Moose becomes scared for his autistic older sister until he realizes the relationship will be ending soon because his sister's second interview with Esther P. Marinoff School is coming up soon. Moose and his family's hopes are crushed when the school rejects Natalie. Out of ideas, Moose decides to take a risk with the help of Piper and writes a letter to the infamous criminal Al Capone, asking him to pull any strings he has to help Moose's family get his sister back into school. Within days, Natalie is accepted into the new branch of Esther P. Marinoff School for older children. The next day Moose is getting ready for the day when he finds a note in the sleeve of his shirt with the word "done" underlined.


Matthew "Moose" Flanagan
12-year-old boy (then 13 years old as of the second book), whose family moves to Alcatraz island from Santa Monica so his father can work as a prison guard and an electrician at Alcatraz island. He's the youngest of the Flanagan family and is very tall for his age.
Natalie Flanagan
Moose's 10 years old sister with autism. But is actually the older sister at the age of fifteen, since at that time there was no treatment for older children and she attends a prestigious school for children with mental issues and her mom just kept her at the age ten.
Cam Flanagan
Moose and Natalie's father. He works on the island as an electrician and a guard.
Helen Flanagan
Mother to Moose and Natalie. She works incredibly hard to have her daughter "cured" to be normal. Her mission is to avoid sending her daughter into a mental institution.
Piper Williams
The Warden's daughter. A determined young woman constantly inventing ways to make money off of her home, Alcatraz Island. Mostly gets in trouble
Warden Williams
The warden of Alcatraz. The strict power enforcer and Piper Williams's father.
Al Capone
A well-known convict and part of the money-making scheme Piper Williams makes up. In real life, Capone was in Alcatraz from 1934 to 1939. One of the most dangerous criminals
Theresa Mattaman
One of the classmates on the island and one of the few people who understand Natalie. Very fun and outgoing who can be friends with anyone.
Jimmy Mattaman
Theresa's older brother, usually more to himself. He likes to play his marble toy
Scout McIlvey
One of Moose's few friends, they play in a baseball team together. Moose eventually tries to find a baseball hit by a con on the island.
Mr. Purdy
The head director of Esther P. Marinoff School.
Ms. Kelly
Natalie's private teacher who is helping her with her social skills.
Convict 105 "Onion"
The convict that Natalie starts to develop a relationship with that Moose fears is romantic. She refers to him as 105, his inmate number. Moose doesn't like him.

Other stories[edit]

It has two sequels, Al Capone Shines My Shoes (2011) and Al Capone Does My Homework (2014).


Critical reception[edit]

Kirkus Review gave the book a positive review, stating "Choldenko's pacing is exquisite, balancing the tense family dynamics alongside the often-humorous and riveting school story of peer pressure and friendship."[4] Miranda Doyle of The School Library Journal says "The story, told with humor and skill, will fascinate readers with an interest in what it was like for the children of prison guards and other workers to actually grow up on Alcatraz Island." [5] Ed Sullivan of Booklist states in his review, "With its unique setting and well-developed characters, this warm, engaging coming-of-age story has plenty of appeal, and Choldenko offers some fascinating historical background on Alcatraz Island in an afterword." [6]

Stage Performance[edit]

In 2011, the book was adapted as a stage performance at The Children's Theatre of Western Springs [7].


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  5. ^ Doyle, Miranda, et al. "Al Capone Does My Shirts (Book)." School Library Journal 50.3 (2004): 203-204. Academic Search Complete. Web. 8 Dec. 2015.
  6. ^ Choldenko, Gennifer. "Al Capone Does My Shirts (Book)." Booklist 100.11 (2004): 976. Academic Search Complete. Web. 8 Dec. 2015.
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External links[edit]