Content Warning: This section of the guide represents ableist attitudes and language present in the source text, which are replicated in direct quotes only.

The protagonist and first-person narrator of Al Capone Shines My Shoes, Moose Flanagan and his family came to live on the island of Alcatraz in January 1935, about seven months prior to the start of the novel, when his father took a job as an electrician and guard at the remote prison. Quick-witted, resourceful, and courageous, the 12-year-old Moose takes on a lot of responsibility for a child of his age; faced with both the dangers and temptations of living in the shadow of a maximum-security prison, he tries, in his small way, to protect his sister, his friends, and his parents in their precarious new surroundings.

His neurodivergent sister, 16-year-old Natalie, is Moose’s greatest source of worry, since her condition makes her vulnerable. In the first book of the series (Al Capone Does My Shirts), Moose helps Natalie get into a special school in the city by asking the convict Al Capone for a favor. In Al Capone Shines My Shoes, Moose worries about the “payback” Capone may demand, and dreads what could happen if his parents or the prison authorities find out about his obligation to the notorious mobster.