Gennifer Choldenko’s Al Capone Does My Shirts (2006) is a work of historical fiction aimed at middle grade readers. The novel is about a family who moves to Alcatraz Island, a small, unprotected island in the middle of San Francisco Bay, in 1935, in the middle of the Great Depression, because the protagonist’s father gets a job at Alcatraz prison. This real life prison formerly housed America’s most infamous, dangerous and ruthless convicts, including historical figures like “Machine Gun” Kelly and Al Capone.

Plot Summary

Narrator Moose (Matthew) Flanagan’s family makes the drastic move from Santa Monica, California, to Alcatraz Island for financial reasons: his father Cam takes a job as an electrician and guard because the Flanagans need the extra income to properly care for Moose’s older sister Natalie, who is on the autism spectrum. In nearby San Francisco, the exclusive private Esther P. Marinoff School specializes in helping children with disabilities like Natalie’s. Moose’s mother Helen dreams of Natalie going there. The is Helen’s dream for Natalie, and it is her mission to have Natalie enrolled there in hopes of curing her condition and avoiding having to send her to a mental institution (a prevalent way of treating people on the autism spectrum at that time in history).

Moose is very unhappy with the move away from Santa Monica. On the island, Moose meets Piper Williams, the trouble-making daughter of the Warden of Alcatraz who also wants off Alcatraz Island and will stop at nothing to earn enough money to do so. Piper exploits her position as daughter of the Warden to intimidate Moose into getting involved with a manipulative scheme—charging her classmates money to have their laundry done at the prison by the infamous real life gangster Al Capone. Many kids that live on the island help Piper run the scheme, but they are eventually caught when a fellow classmate feels cheated.

Moose tries to hide Natalie from the other children as he is embarrassed by and protective of her. However, once the children meet her, they accept her and help Moose look after her when his mother takes on piano students to help make ends meet.

Natalie’s first stay at the Esther P. Marinoff School is unsuccessful. She is sent home less than two days after she is dropped off because she is “not ready for the program” (61). Mr. Purdy, the man responsible for her enrollment, suggests that she work with a tutor named Mrs. Carrie Kelly to prepare for the school.

Working with Carrie and spending a lot of time with Moose improve Natalie’s communication and social skills—she learns, in particular, to refer to herself in the first, rather than the third, person. Sometimes, Moose feels cruel for not allowing Natalie to engage with items she has fixated on (a box of buttons, books with indexes, etc.). Recognizing that these objects are part of Natalie's identity, he decides it is ok for her to interact with them when they are alone.

While trying to look for a lost convict’s baseball, convict #105 and Natalie strike up a friendship that terrifies Moose. He learns from Piper that this inmate is a seemingly decent young man who is soon to be released.

When the Esther P. Marinoff School rejects Natalie a second time, Moose feels helpless. He decides that that Al Capone could convince Mr. Purdy to allow Natalie to attend. Piper helps Moose write a letter to Al Capone, asking for his help and miraculously, it works. When Moose gets his laundry back from the prison, he finds a note in his shirtsleeve that simply says, “Done.” The family learns that Natalie will be the first student in the school’s new section for older children.