57 pages • 1 hour read
Al Capone Shines My Shoes
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Series Context: Gennifer Choldenko’s Tales from Alcatraz
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. Choldenko’s late sister was, like Natalie, on the autism spectrum. Choldenko asserts that the prison island’s mist-wrapped isolation evokes for her the prison-like seclusion of her late sister’s condition, which may have led to her early death. Despite the prison island setting of her book series, Choldenko combines her books’ serious themes with slapstick humor, lively wordplay, and more-or-less happy endings.
Biographical Context: Al Capone
Al Capone was a famous gangster during the Prohibition Era (1920-1933) in the United States. He was born on January 17th, 1899, to an Italian immigrant family, and was raised in Brooklyn in New York City. He left school while still in his teens and worked a series of odd jobs before joining a gang and embarking upon a life of crime. He earned his nickname, “Scarface,” after his face was slashed during an altercation with another man. At age 26, Capone became a crime boss and an influential figure in the American Italian mafia.
From 1925-31, Capone was a fixture of the world’s tabloids, newspapers, and magazines as he gained fame for his criminal activities. His crime ring was especially notable for bootlegging—the production and smuggling of illegal alcohol, which circumvented the USA’s Prohibition laws. Capone also tried to court popular opinion by contributing to nationwide charities. He was, however, noted for his violence and ruthlessness: In 1929, Capone orchestrated the St. Valentine’s Day Massacre, a gruesome mass execution of seven unarmed members of a rival gang. The event was widely reported in the media.
In 1931, Capone was arrested and charged with tax evasion. He was found guilty and sentenced to 11 years in prison. He began serving his sentence in the Atlanta US Penitentiary in 1932 before getting moved to Alcatraz in 1934. During Capone’s four-year stay at Alcatraz, he suffered extensively from an untreated case of syphilis, resulting in neurosyphilis that damaged his brain and caused delusions. He was released early from prison in 1939 on the grounds of ill health. In 1942, he became one of the first patients to be treated with penicillin, but by then it was too late to reverse the effects. He spent his last years of life with his family, with his health continuing to rapidly deteriorate. Capone died of heart failure in 1947 at the age of 48, eight years after his release from Alcatraz.
Capone’s rise and fall has lived on in the public imagination, inspiring countless books, movies, and stories drawn from his life. The two Scarface films are perhaps the most famous examples. In the Tales from Alcatraz series, Capone appears as an important character, with the prisoner continuing to scheme from behind bars.
Geographical Context: Alcatraz
During the 1849 California Gold Rush, the US Army built a fortress on Alcatraz island to protect the city's growing wealth from invasion. By the late 1850s, much of the island had been requisitioned as a military prison. In 1933, the federal government, alarmed by soaring crime rates, converted the rocky island into a maximum-security prison for some of the country’s most dangerous convicts. Although located only 1.25 miles from San Francisco, Alcatraz was washed by cold, swift currents that made escape virtually impossible. This earned the prison its nickname of “The Rock.”
As depicted in Choldenko’s books, the prison’s personnel also lived on the small island with their families. Guards were billeted on the island to ensure a quick response to unrest, and most lived in Building 64, the oldest structure on Alcatraz. Formerly the barracks of the island’s 1850s military fortress, Building 64 was converted into civilian apartments when Alcatraz was made into a federal penitentiary. As shown in the books, convicts often carried out repairs and other work in Building 64, as well as doing all of the island’s laundry. Al Capone, who arrived at the prison shortly after it opened in 1934, was assigned to the laundry. In 1983, Alcatraz ceased operations and has since become a popular tourist site.
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