Al Capone Does My Homework, Gennifer Choldenko’s 2013 novel about a boy living on Alcatraz Island with his family, is the third book in Choldenko’s young adult series, Tales from Alcatraz, which follows the adventures of Moose Murphy and his teenage sister, Natalie. The series combines 1930s history with elements of humor, mystery, and suspense while exploring issues of morality, sociology, and developmental health. Natalie, for instance, has a developmental disability, which complicates the family’s daily life and livelihood in a time and place where her condition is widely misunderstood. Moose, the books’ narrator and protagonist, who turns 13 during the series, cares for his older sister while grappling with the many pressures, dangers, and temptations of being part of the civilian population of Alcatraz, America’s “roughest prison.”

The first book in the series, Al Capone Does My Shirts, was shortlisted for the Newbery Medal and won a Newbery Honor as well as 20 other awards. As of 2024, the four novels of Choldenko’s Tales from Alcatraz series have sold over two and a half million copies. Each is a stand-alone narrative that does not require familiarity with its predecessors.

This guide refers to the 2013 Puffin Books paperback edition of Al Capone Does My Homework.

Plot Summary

Thirteen-year-old Moose Flanagan, whose father has just been promoted from electrician to associate warden of Alcatraz Federal Penitentiary, struggles with the many pressures of living on the notorious prison island. His father, Cam, who Moose believes is “too nice” to be a warden, has inadvertently made an enemy of the guard Darby Trixle, who wanted his promotion. Adding to his stress, Moose discovers that the convicts have put a price on the heads of guards and wardens in the form of a “points game.” Killing a warden, he learns, is worth 5,000 prestige points. Donny Caconi, a friendly adult who regularly visits the island, tells Moose that his father is in a “tight spot,” caught between Darby on one side and the cons on the other.

In addition to worrying about his father, Moose must help look after his 16-year-old sister, Natalie, who has a developmental disability and has difficulty with communication and social interactions. Natalie refuses to make eye contact with others, shows repetitive behavior, and communicates mostly by repeating others’ words. However, she loves numbers and counting and can solve complex multiplication problems with barely a glance.

The very night of Cam’s first day as associate warden, the Flanagans’ apartment catches fire, and Moose and Natalie narrowly escape by breaking a window. Darby Trixle and his wife, Bea, who live in the same apartment building, accuse Natalie of starting the fire, referring derogatorily to her developmental disability and arguing that she poses a danger to the other residents of Alcatraz. Moose defends her but cannot be sure of her innocence since he accidentally fell asleep while watching her.

Moose and his friend Piper, the warden’s daughter, suspect that the fire has some connection with his father’s promotion. Together with Moose’s friends Annie, Jimmy, and Theresa, they form a “team” to investigate the fire. While searching for clues, they stumble upon some mysteries: Moose finds $40 hidden in the Caconis’ laundry bag; a butcher knife disappears from the cellblock kitchen; $50 goes missing from the Trixles’ grocery; and a convict named Count Lustig is seen hiding a scrap of paper marked with strange numbers in a waterspout, presumably for an accomplice to find. Another convict, the mobster Al Capone, leaves a cryptic message (“State problem”) on Moose’s school essay on polio and Franklin D. Roosevelt, which briefly disappeared during the fire. Meanwhile, Piper, who has been showing off money and gifts she has been given, supposedly by a “secret admirer,” seems increasingly agitated but won’t say why.

At a poker party hosted by Moose’s father, Natalie uses her prodigal counting abilities to spot a card cheat, who turns out to be Donny Caconi. The next day, Moose, Piper, and Annie eavesdrop on Mr. Flanagan’s interrogation of Al Capone, but the mobster claims to know nothing about the fire or the missing knife. However, Cam’s mention of money and gifts “floating around,” combined with recent news reports about counterfeit money flowing into San Francisco, brings Piper close to panic. Finally, she confesses to Moose, and then to her father (the warden), that she has been enriching herself by leaving money in her dirty laundry, which comes back doubled each time. The laundry cons, she now realizes, have been using her to circulate counterfeit bills. A week later, the task force investigating the fire in the Flanagans’ apartment concludes that Donny is guilty of the arson; Moose and his friends also suspect Donny of smuggling the counterfeit money into Alcatraz in his laundry bag, at the behest of Count Lustig.

Moose finally deciphers Al Capone’s message about a “State problem” just in time to save his father’s life when a convict named Indiana attacks him with the stolen knife. However, his father is critically injured and must be taken to a hospital in the city. A few days later, Moose coaches Natalie, who wants to visit their father, on how to pass as “normal” to get past the reception desk; in doing this, he goes against the wishes of his mother, who wants to keep Natalie out of the public eye because of widespread misapprehensions about developmental disabilities. However, Natalie, under Moose’s guidance, successfully hides her condition from the receptionist and is allowed into the building, forcing her mother to recognize her budding independence.

Eleven days later, Cam returns home, a bit shaky on his feet but determined to continue his service as Alcatraz’s associate warden. He commends Moose on all he has done for the family, including helping Natalie become more independent. Meanwhile, Darby Trixle’s seven-year-old daughter, Janet, tells Moose that her imaginary “pixie” friends know something about the fire. Her father, she hints, paid Sonny Caconi to burn down the Flanagans’ apartment, presumably to drive them from the island so Darby could have Cam’s job. Moose tells his father, who seems skeptical but says he will notify the warden. Soon afterward, Moose and Natalie run into Donny Caconi, who is out on bail for arson. Donny, intrigued by Natalie’s card-counting abilities, tries to tempt her into running a scam with him. However, she looks him straight in the eye and says, “Alcatraz three hundred and seventeen”: the number of Alcatraz’s next prisoner, presumably himself (204). Moose observes that when it comes to numbers, Natalie never errs.