Al Capone Shines My Shoes

Al Capone Shines My Shoes (2009) is the second book in Gennifer Choldenko’s Tales from Alcatraz series. The novel is set on the prison island of Alcatraz during the height of the Great Depression. The protagonist and narrator is 12-year-old Matthew “Moose” Flanagan, whose father works as a guard and electrician at the notorious prison. When Moose receives a note from Al Capone, a famous gangster and prisoner of Alcatraz, he finds himself caught up in various misadventures and moral dilemmas.

This guide uses the 2011 Puffin Books paperback edition.

Content Warning: The source text features ableist attitudes and language, which are replicated in this study guide in direct quotes only.

Plot Summary

The novel is set in 1935. Moose Flanagan, the novel’s 12-year-old protagonist and narrator, lives on the prison island of Alcatraz with his parents and 16-year-old sister Natalie, who has autism. His father, Cam Flanagan, moved the family from Santa Monica seven months earlier so that Natalie could attend the Esther P. Marinoff School for neurodivergent students in nearby San Francisco. Cam works in Alcatraz as a prison guard and electrician and lives with his family in 64 Building, an apartment house shared by most of the island’s civilian population.