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. Since autism is widely misunderstood at this time, Natalie faces prejudice and distrust on Alcatraz, especially from the ill-tempered guard Darby Trixle, who considers her a threat to the island’s security.

In the preceding (first) book of Choldenko’s Tales from Alcatraz series, the Marinoff School rejected Natalie as a student; in desperation, Moose secretly wrote to the gangster Al Capone, Alcatraz’s most famous convict, for help. Since Capone and other convicts do the island’s laundry, Moose sent his letter by slipping it into the pocket of one of his dirty shirts, and within a few days a handwritten answer came back in his clean laundry: “Done.” Subsequently, Natalie was accepted by the Marinoff School. In the present book, however, Moose worries about what “payback” the mobster might demand for his favor.

One day, Moose’s friend Annie Bomini, a girl his own age with whom he plays baseball, is given the Flanagans’ bag of laundry by mistake and finds a scrawled message meant for Moose. Presumably from Al Capone, it says, “Your turn.” Moose is forced to tell Annie what he has done, and she warns him that Capone might have him killed if he fails to do this (as yet unspecified) deed. On the other hand, if he does do Capone a favor and the prison authorities find out, his father could be fired, his family could be kicked off the island, and Natalie will have to leave her school.

Seeking to distract himself with his favorite sport, Moose invites Scout, a school friend who excels at baseball, to the island. However, Scout’s visit creates friction between Moose and his Alcatraz friends, particularly his best friend, Jimmy. Scout also annoys Moose by flirting with his (sometime) girlfriend Piper Williams, the warden’s pretty but self-centered daughter. To save money, Warden Williams has recruited two convicts to work for him during his wife’s pregnancy: Buddy Boy, a convicted conman who serves as houseboy, and Willy One Arm, a one-armed pickpocket who handles the cooking. Buddy Boy is an expert impressionist and can do an uncanny impersonation of Shirley Temple.

By mid-August, Natalie has been doing so well at her boarding school that Moose’s worries have eased. However, he then finds a note from Capone under his pillow, presumably left there by Seven Fingers, a convicted axe murderer who services the family’s plumbing. It specifies the favor the gangster wants from him: “My Mae loves yellow roses” (53). Somehow, Moose must present roses to Al Capone’s wife—without being seen by the guards—when she boards the Sunday ferry to Alcatraz. Visiting the local grocery, where his friend Jimmy Mattaman works, Moose saves Rocky, Jimmy’s baby brother, from choking to death by rushing him to the doctor. This angers Piper, who wanted to prove herself by running the baby to the clinic herself; she is particularly incensed that Moose was given a tour of the cellblock as a reward and got to meet Al Capone.

To distract Jimmy’s sister Theresa from her guilt over neglecting the baby, Moose invites her along when he visits Natalie’s school on Sunday. However, his hopes of using her to deliver the yellow roses to Capone’s wife are dashed when he sees hordes of reporters trailing after the beautiful Mae Capone, alongside Darby Trixle and the warden himself. If Moose is caught doing a favor for Capone’s wife, his father will be fired, so he hides his actions by splitting his six roses between Mae and five other females on the boat, including Annie and Theresa. Unfortunately, news of his generosity reaches the jealous Piper. Shortly afterward, when he and Piper are about to share a kiss in a crawlspace, Theresa barges in and insults her. Moose, not wanting to offend Theresa, fails to defend Piper, who, enraged, lies to her father that she saw Moose’s and Theresa’s fathers drinking on the job. As a result, Mr. Flanagan and Mr. Mattaman are put on probation. Now, any dereliction of duty could get them fired.

As Mr. and Mrs. Flanagan escort Natalie back to Alcatraz for a visit, Natalie sets off the boat’s metal detector. Cam and Mr. Mattaman, looking in her suitcase, determine that the culprits are the metal buttons in Natalie’s prized button collection. However, back at home, Moose and Jimmy find a “bar spreader”—a tool used to push cell bars apart—hidden in her suitcase. Moose suspects that “Onion,” a former Alcatraz convict who has become friendly with Natalie, gave it to her so that one of his accomplices on Alcatraz could use it in a jailbreak. Knowing that if the authorities find out about it, their fathers will be fired, Jimmy volunteers to throw it in the bay; unfortunately, his throw is weak, and Janet, Darby Trixle’s seven-year-old daughter, finds it on the beach.

The next day, the convict Seven Fingers visits the Flanagan house, ostensibly to fix the plumbing. Not finding the bar spreader in Natalie’s dresser, he corners Moose and threatens to harm Natalie. Later that day, Moose visits Piper and asks her to retract her false allegation against his and Jimmy’s fathers. She agrees, but only if Moose does her a favor.

The next day, the warden hosts an elaborate party for FBI director J. Edgar Hoover and Eliot Ness, the lawman who put Al Capone behind bars. Piper forces Moose to help her peek into the kitchen, where they see convicts performing the roles of cooks and waiters. From their hiding place, they watch as Al Capone, dressed as a server, spits into food that was prepared for Hoover and Ness. The next morning, Moose learns that Piper’s mother is in a hospital in the city, gravely ill from pregnancy complications. Later, urged by Mrs. Mattaman, Moose tries to comfort Piper, who tells him she doesn’t want a baby brother. Crying, she confesses that she wanted her mother’s baby to die. Moose coaxes her into accompanying him to Jimmy’s, where Mrs. Mattaman warmly embraces her. Tearfully, Piper apologizes for falsely accusing Mr. Mattaman and Mr. Flanagan.

On a day thick with fog, Warden Williams returns from his vigil at the hospital in high spirits, handing out cigars and shouting that he has a son. Mrs. Mattaman tells Moose that Mrs. Williams almost died but is expected to recover. The warden, she says, has brought their new son (Walter) home to Alcatraz without her. In fact, he is hosting a big party to celebrate his birth, which his wife will miss because she is still recuperating in the hospital. Moose, Natalie, and Theresa go to the Williams’s house, where they help Piper tend to her new baby brother, whose caretaker (Mrs. Caconi) has fallen asleep. Piper refers to the baby as “It,” and claims she wants nothing to do with him.

Hearing a voice like Jimmy’s calling to them from outside, Moose and Piper, followed by Natalie, go down to let him in. Piper reluctantly takes the baby with her. The voice is actually Buddy Boy’s mimicry of Jimmy, and he and Seven Fingers and Willy One Arm seize the three children. The three convicts have disguised themselves as guards, complete with guns, and their plan is to escape on a motorboat, using the children as hostages. The thick fog provides the perfect cover for their escape. Since Baby Walter’s crying threatens to give them away, Willy One Arm grabs him away from Piper and carries him off, returning empty-handed after a short time. As they near the dock, Natalie starts counting out loud, saying the convicts have “five arms” and “no guns.” Realizing that his sister is never wrong about counting, Moose screams for help, shouting that the men have no guns. Buddy Boy strikes Moose with his “gun,” which is actually a piece of wood.

Seconds later, the Alcatraz children come to their rescue: Jimmy by releasing his trained flies at the convicts, Janet Trixle by shouting at them through her bullhorn, and Annie by pelting them with rocks. Guards swarm the dock, and the convicts are apprehended. As Moose’s father leads the children to safety, Piper screams wildly that her brother is missing and that she has to find him. Natalie runs off by herself, following a mouse that belongs to one of the convicts. It leads her into the cellhouse and to the cell of Al Capone, who is cradling Baby Walter tenderly in his arms. When Moose and his father arrive, Capone hands over the baby, saying he was only doing a little “babysitting.” It turns out that Capone aided the three convicts’ escape to a limited extent but refused to go with them.

The seven children are celebrated on Alcatraz for their heroism, especially Natalie, who surprised many with her alertness in spotting the fake guns and finding the missing baby. Meanwhile, the prison authorities find the bar spreader among Janet Trixle’s toys, putting Darby under suspicion. Moose demonstrates his integrity by telling his father that it was Natalie who smuggled it onto the island, not Darby. In turn, his father insists on doing the “right thing” by telling the warden. A few days later, another note arrives for Moose, hidden in Natalie’s newly-laundered yellow dress: “Good job,” it says.