Al Capone Shines My Shoes, the second novel in Gennifer Choldenko’s Tales from Alcatraz series for young adults, continues the saga of 12-year-old Moose Flanagan, whose family moves to Alcatraz in 1935 when his father finds work as a guard and electrician at the infamous prison island. The series follows the adventures of Moose, his sister Natalie, a 16-year-old who has autism, and their small circle of friends and acquaintances. The real-life gangster Al Capone also appears in the books’ storylines: Although confined to a small jail cell, Capone attempts to communicate and orchestrate things from behind bars. The four Tales from Alcatraz books are, in sequence, Al Capone Does My Shirts (2004), Al Capone Shines My Shoes (2009), Al Capone Does My Homework (2013), and Al Capone Throws Me a Curve (2018). Each is a stand-alone narrative that does not require familiarity with the rest of the series. As of 2024, Choldenko is reportedly working on a fifth book.

Choldenko lives in San Francisco and was inspired to write the books by her longtime fascination with Alcatraz, which is now a popular tourist site. Her research involved working as an Alcatraz tour guide and conducting interviews with former residents, some of whom lived on the island as children in the 1930s, the timeframe of her novels.