Al Capone Does My Homework

The bestselling author of more than a dozen books, Gennifer Choldenko is best known for her Tales from Alcatraz series, the first of which (Al Capone Does My Shirts) won a Newbery Honor in 2005. This young adult novel introduces the character of Moose Flanagan, a 12-year-old who lives on the Alcatraz prison island along with his parents and 16-year-old sister, Natalie, who has a developmental disability. Al Capone Does My Homework, the third book in the series, hinges on the promotion of Moose’s father from electrician to Alcatraz’s associate warden, which puts him and his family in increased danger. Choldenko has since written a fourth Alcatraz novel, which she says will probably be the last.

To her books’ carefully researched verisimilitude of 1930s Alcatraz, Choldenko adds some notes of autobiography. Though the Tales from Alcatraz series unfolds over 18 months in the years 1935 and 1936, some of its events harken back to Choldenko’s own childhood in 1960s Southern California, particularly a traumatic span of months when she was 12. Within less than a year, Choldenko lost her father, uncle, grandparents, and her sister, Gina, who had autism. These tragedies, she says, upended her life, emotionally stunting her for years at the age of 12. Creating the Alcatraz series and other books, she says, has helped her commune with, and nurture, this traumatized inner child, lending her young-adult fiction a resonant, authentic voice. “When I write,” Choldenko says, “I write from the deepest part of who I am and that’s the part that’s twelve” (“Gennifer Choldenko: Orphan Eleven (Trauma, Speech Difference).” A Novel Mind, 22 Sept. 2021). Moose Flanagan, the youthful narrator of her Tales from Alcatraz books, has also had his life capsized at age 12 by his family’s move to Alcatraz, where they must live side-by-side with some of the world’s most dangerous criminals. Other real-life parallels include Moose’s older sister Natalie—who, like Choldenko’s sister Gina, has a developmental disability, although she is not formally given the diagnosis of autism in the series—and Moose’s love for baseball, which alludes to Choldenko’s older brother, who played on a team. Her brother, she says, was as dedicated to Gina’s care as Moose is to Natalie’s.

Alcatraz Federal Penitentiary, a maximum-security prison located on a small island 1.25 miles off the coast of San Francisco, operated for only 29 years, from 1934 to 1963. Over that span, however, it became famous as the final destination of some of the world’s most notorious criminals, including the mobsters Al Capone, Machine Gun Kelly, and Mickey Cohen: “the cream of the criminal crop” (223). In the 1990s, Choldenko, who lives in the San Francisco Bay Area, became fascinated with Alcatraz and its history, which struck her as an ideal subject for a novel. In 1998, as part of her research, she worked as an Alcatraz tour guide, which gave her a feel for the island’s picturesque yet unsettling ambiance. While planning Al Capone Does My Shirts, she interviewed dozens of former guards, prisoners, and residents, including some who had lived there as children as far back as the 1930s, an era that particularly interested her. Much of this material found its way into her books, including the cons’ use of cockroaches to deliver messages, the spartan amenities of the residents’ homes, and the fact that the convicts did laundry for everyone on the island. One vivid anecdote that stayed with her was that, since sound travels easily over water, the convicts of Alcatraz could hear the carefree sounds of revelers at holiday parties in San Francisco. As with Moose’s sister Natalie, and Choldenko’s own sister Gina, the convicts’ isolation was deepened by their knowledge of others’ togetherness and happiness. Autism, Choldenko feels, can be a prison unto itself, and the remote beauty of Alcatraz island always reminds her vividly of her sister, who may have taken her own life. In her Tales from Alcatraz series, with its humor, drama, mysteries, and sense of community, Choldenko imagines a better fate for Gina/Natalie, dramatizing the lifesaving powers of resilience, love, and personal connection even in the loneliest of places.