Al Capone Does My Shirts

Moose Flanagan and his family composed of father Cam, mother Helen, and sister Natalie move from Santa Monica to Alcatraz Island in 1935. The move was caused by Cam's new job as an electrician and guard at Alcatraz prison. The Flanagans pretend that Natalie, who is sixteen and has autism, is only ten in hopes of gaining her admission to the Esther P. Marinoff School, an off-island school for children with mental illness directed by a Mr. Purdy. This lie is encouraged by Moose's mother, who believes that the Marinoff School is Natalie's only hope for a cure and wants to avoid sending Natalie to a mental institution. Due to his parents' hectic work schedules, Moose is left with almost full responsibility of Natalie, while also trying to fit in at his new off-island school. Natalie is accepted into the Esther P. Marinoff School, but is sent back home almost immediately, because she's having trouble adjusting. Moose's mother and Natalie's new psychologist, Mrs. Kelly, push Moose into 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, a girl he clearly likes, who regularly gets into trouble in her attempts to earn money to get off of Alcatraz. Piper talks him into being part of her money-making schemes, like having inmates on the island do laundry for the kids at school. When the scheme flops and the Warden receives word of it, the children are punished and have to find a new way to spend their time. In an attempt to gain acceptance, Moose hangs around the prisoners' rec center in hopes of finding a stray baseball for use in games with the other kids. Moose eventually notices his older sister Natalie developing a relationship with convict 105, also known as Onion, who is trusted and able to roam freely because his sentence is almost up. Onion knows Moose has been looking for a baseball and gives him one. Scared of his sister hanging out with a convict, Moose is only reassured because of his confidence that she will be re-accepted to the Marinoff School. Moose and his family's hopes are crushed when the school rejects Natalie. Desperate to help Natalie, Moose decides to take a risk, with the help of Piper, and writes a letter to the infamous criminal Al Capone, who works in Alcatraz's laundry. The letter asks Capone to pull any strings he has to help Moose's family get his sister back into school. Within days, Natalie is accepted into a new branch of the 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.

It has three sequels, Al Capone Shines My Shoes (2011) and Al Capone Does My Homework (2014) and Al Capone Throws Me a Curve (2018). A new book is in development.

• Newbery Honor
• California Young Reader Medal

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]

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

In 2019, the book was adapted as a stage performance at Mission Cultural Center by the San Francisco Youth Theatre.

• Author webpage
• Publishers Weekly review
• Publisher webpage