Al Capone Does My Shirts Study Guide

Choldenko was born in Santa Monica, California, the youngest of four children. One of her older sisters, Gina, had severe autism, and Choldenko based the character of Natalie partially on Gina. After earning a BA from Brandeis University in English and American Literature and a BFA from the Rhode Island School of Design in illustration, she held numerous odd jobs, including working in sales and teaching horseback riding to hearing and visually impaired children. Though Choldenko notes that she comes from a long line of writers and has always loved writing, she only began writing professionally in 1997, when she published her first picture book. She began writing novels in 2001, and her second novel, Al Capone Does My Shirts, was a Newbery Honor book. Choldenko has written a number of novels for children and teens since then, including three more in the Alcatraz series, as well as several picture books. She lives in the San Francisco Bay Area.

While there’s been a fort on Alcatraz Island since the 1850s, the island didn’t become the prison Moose describes in the novel until the U.S. government purchased the island in 1933 and renovated the crude army prison on the island. The United States Penitentiary, Alcatraz Island—or just Alcatraz—opened in 1934 and was operational until 1963. A maximum security federal prison, it was intended to house prisoners who caused problems consistently at other facilities. From the beginning, Alcatraz gained notoriety, mostly due to housing some of the most notable criminals of the day. These included Al Capone, a Chicago gangster believed to be responsible for around 200 murders (as well as for opening the first soup kitchen in the city), and “Machine Gun Kelly,” a Memphis gangster best known for kidnapping Charles Urschel, an oil tycoon, and collecting a $200,000 ransom. Choldenko has said in supplemental materials for Al Capone that Natalie would likely be diagnosed with autism were she alive today, though in 1935, the diagnosis didn’t exist. Psychiatrists initially grouped autism in with schizophrenia—and this persisted until the 1970s. Autism exists on a spectrum (formally, it’s known as Autism Spectrum Disorder, or ASD) and symptoms can include avoiding eye contact, repetitive or limited interests or movements, and difficulty in social situations. Since the 1980s, there’s been a push to recognize autism as a disability and as the result of brain differences, rather than as a disease that can or should be cured. The novel obliquely alludes to this dichotomy: while Mom wants to “cure” Natalie, Moose falls more on the side of accepting Natalie for who she is.

Al Capone Does My Shirts is the first in a series following Moose’s childhood on Alcatraz. It’s followed by Al Capone Shines My Shoes, Al Capone Does My Homework, and Al Capone Throws Me a Curve. Several of Choldenko’s other novels are historical fiction, notably Chasing Secrets and Orphan Eleven. In the supplemental materials for Al Capone, Choldenko lists Temple Grandin as an influence on how she portrays Natalie and autism. Temple Grandin is autistic and is best known for her work developing systems to manage cattle prior to slaughter, but she’s written several books and dozens of scientific papers on autism. Her best-known books include Thinking in Pictures: My Life with Autism and The Autistic Brain: Thinking Across the Spectrum. Other novels for young readers that deal with similar themes of disability and acceptance include Sharon Draper’s Out of My Mind, which features a protagonist with Cerebral Palsy; and Lynda Mulalley Hunt’s Fish in a Tree, whose protagonist struggles prior to receiving a diagnosis and resources for her dyslexia. For a closer look at Al Capone, Deirdre Bair’s Al Capone: His Life, Legacy, and Legend humanizes the legendary gangster, focusing on his close-knit family and drawing on interviews with Capone’s descendants.