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57 pages 1 hour read

Al Capone Shines My Shoes

Fiction | Novel | Middle Grade | Published in 2009

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Chapters 1-9 Chapter Summaries & Analyses

Chapter 1 Summary: “The Cream of the Criminal Crop”

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

Twelve-year-old Moose Flanagan lives on the bleak prison island of Alcatraz, where the mobster Al Capone and 277 other hardened convicts are serving time. His father, Cam Flanagan, brought the family to Alcatraz seven months earlier, in January 1935, to work as a prison guard and electrician. Moose, his parents, and his 16-year-old sister Natalie share a small apartment in Building 64, the island’s civilian quarters. They sometimes have their plumbing repaired by the convict Seven Fingers, an axe murderer.

The prisoners perform many other services on the island: Al Capone and the notorious Machine Gun Kelly are among the cons who do the island’s laundry. Other, unpopular guards, such as the brutish Darby Trixle, sometimes get their clothes back vandalized, but Capone seems to have a soft spot for the Flanagans: Moose even believes that the mobster pulled strings on his behalf to help get his sister Natalie, who has autism, into a special boarding school in the city, the Esther P. Marinoff School. The school had already turned Natalie down twice, so Moose left a note in his laundry for Capone asking for his help. Soon afterward, Natalie was accepted, and Moose received a note in his clean laundry with a single word: “Done.” Moose has not shared this with his parents. He wonders sometimes why the infamous Capone would want to help him.

On Monday, August 5th, 1935, Moose and his parents walk Natalie to the dock so she can take the ferry to San Francisco for her first day of school. Natalie, whose behavior and intellect can be alarmingly unpredictable, appears to be in a stable mood. She wears a yellow dress and clutches her prized button collection. At the dock, however, the boorish Darby Trixle orders the tower guard to fire warning shots at a tourist boat that has strayed too close to the island. The shots scare Natalie, who hates loud noises. Darby, smirking at Natalie’s panicked reaction, threatens to “report” it to the warden. Natalie, however, soon calms and boards the ferryboat by herself. As her family waves goodbye, she departs for her boarding school in the city.

Chapter 2 Summary: “The Secret Passageway”

Moose and his best friend Jimmy Mattaman, also the son of a guard, have found a secret way of entering a crawlspace under 64 Building by unscrewing the door hinges. Nicknaming the passageway “Chinatown,” the boys use it as a hideaway and as a way of eavesdropping on the building’s adults, who often have conversations in the apartment of the childless Mrs. Caconi.

In the passageway, Moose invites Jimmy to play baseball with him later in the day, since Scout, one of Moose’s friends, will be visiting from the city. Jimmy is not good at baseball and his interests are more science-oriented; he is currently collecting hundreds of flies so he can teach them tricks and hold a “circus.” Jimmy hopes that Scout will like him, despite his lack of skill at baseball.

As the two boys sneak out of the crawlspace, they are almost caught by Darby Trixle, who sees Jimmy and berates him through his bullhorn for loitering in the basement. He reminds Jimmy to report to work at the grocery run by Bea Trixle, Darby’s wife. Moose remains in hiding; he feels he is particularly hated by Darby because of Natalie, whose condition annoys Darby. After Darby and Jimmy leave, Moose climbs the stairs to the apartment of Annie Bomini, a close friend of his who excels at baseball. However, Moose is upset to hear that Annie was given his family’s laundry bag by mistake and found a handwritten note in his shirt pocket with the words, “Your turn.” He recognizes the handwriting as Capone’s and realizes that the gangster now expects Moose to do him a favor in return for getting Natalie into her special school.

Annie demands to know what is going on, and Moose confesses on the condition that she not tell anyone. He adds that Piper Williams, the warden’s daughter, also knows about the favor from Capone. Annie, shocked, says Capone will likely kill Moose if Moose doesn’t do what Capone wants. On the other hand, she says, if Moose does do a favor for Capone and the warden finds out, his father could be fired. Reminding Annie of her promise not to tell, Moose suggests that she forget all about it and join him in a game of baseball—his favorite distraction whenever he is worried.

Chapter 3 Summary: “Willy One Arm”

Moose and Annie play catch on the parade grounds, a large concrete lot on the middle tier of the island. Annie, still upset over their discussion, throws erratically. They are joined by Piper, who is on roller skates, casually breaking one of the island’s rules. Sensing the tension between them, Piper tells them to “kiss and make up,” whereupon Annie teases her back about her own attraction to Moose. Piper tells Moose that she has two convicts working in her house to help out her pregnant mother: Willy One Arm, a former thief, who does the cooking, and Buddy Boy, a con artist, who serves as their houseboy. After Piper leaves, Darby Trixle arrives on the parade grounds with his seven-year-old daughter Janet, both of them carrying bullhorns. Darby tells Moose that Scout arrived on the 10 o’clock ferry, but that he sent him back because his paperwork wasn’t in order, due to a mix-up about the time he was supposed to board. Moose runs down to the dock and discovers that Darby waited 20 minutes to tell him, making sure that he would miss his friend.

Chapter 4 Summary: “Murderers and Madmen”

Moose takes the next boat to San Francisco and joins up with Scout, who can’t wait to play baseball on Alcatraz. Coming back on the one o’clock ferry, the two boys go straight to Annie’s to ask her to play, but she says she won’t play until Moose tells the warden about the note from Capone. Moose argues that his sister’s schooling is worth the risk of being hurt or killed by Capone, but Annie scoffs at this, claiming that “everybody else” knows that Natalie’s special school won’t make her “normal.” Moose angrily gives up but then finds himself defending Annie’s baseball skills to Scout, who jeers at the thought of her being much good.

As they practice pitching and batting, Scout asks Moose if he can get him a baseball used by a convict. Moose mentions that Piper has two convicts working in her house, and the boys decide to visit her. Mrs. Wiliams greets them warmly and introduces them to Buddy Boy. Buddy Boy’s low, insinuating voice unnerves Moose, but Buddy impresses him by doing a passable impression of Cam Flanagan’s voice; somehow he even knows that Moose’s father calls Natalie “sweet pea.” Piper appears, excited to see Scout again, and the two of them stroll to the kitchen to visit Willy One Arm, who has just baked brownies. Willy shows them a “sleeve trick,” using his shoulder to spin the empty sleeve of his missing arm around like a whirligig. He also shows them Molly, his pet mouse, whom he keeps in his pocket.

As the three kids eat their brownies, Piper tells Moose that Scout is “cute,” clearly trying to make him jealous. As the boys leave the house to play baseball, Moose scolds Scout for being so friendly with Piper. Scout retorts that any girl who shares her house with “murderers and madmen” deserves a little kindness (38).

Chapter 5 Summary: “Auntie’s Revenge”

Moose and Scout head over to the Mattamans’ apartment, where Jimmy and his seven-year-old sister Theresa share a bedroom filled with signs of their respective hobbies, such as Jimmy’s book about flies and Theresa’s newspaper articles about famous outlaws.

Jimmy starts to tell Moose and Scout about his experiments with flies, but Scout cuts him off, eager to start the baseball game. Jimmy agrees to play, and Theresa manages to talk Annie into joining them on the field. However, Annie is still angry at Moose for not telling the warden about Capone and insists that he sit the game out. Moose is shocked that Scout does not come to his defense; moreover, Scout offends Jimmy by telling him he throws like a “dead girl.” When it is Scout’s turn to bat, he and Annie focus on each other and ignore Moose, who keeps begging to play. Annie gets two strikes on him, but then Scout, in a rage, hits the ball clear over 64 Building and onto the dock, where the axe-murderer Seven Fingers picks it up and throws it back.

When Moose walks back to the field, Scout asks him if he can have the baseball, since it was thrown by an axe-murderer, making it a “convict baseball.” Moose reluctantly agrees, dismaying Jimmy, who thought he was Moose’s best friend. Scout gratifies Annie by telling her she’s good enough to play on his team in the city.

Chapter 6 Summary: “What Capone Wants”

Monday, August 12th, 1935: Moose’s mother returns from a visit to Natalie at her boarding school, saying Natalie has settled in well. As Moose and his father play darts, Cam advises his son to try to be a little more tolerant of people like Darby Trixle, saying that he himself always looks for the good in others. He adds that, unlike Darby, he believes in treating the convicts with respect, which he thinks will help make them better people. All the same, they can be trusted only so far. He worries about the warden’s policy of using Buddy Boy and Willy One Arm for free labor, which he thinks may be a little naïve.

Thinking about his letter to Al Capone, Moose asks if his father ever did “the wrong thing for the right reason” (52). Cam says that when he first met Moose’s mother, she was dating his cousin Harold, but that did not deter him from wooing her, and he has never regretted it. Moose’s mother, buoyed by her visit with Natalie, enters in a cheerful mood, and she and Cam discuss getting a piano so she can play at home. Moose goes to bed feeling happy. Under his pillow, however, he finds a note, presumably left by Seven Fingers, who has just fixed the plumbing. It says, in Al Capone’s handwriting, “My Mae loves yellow roses. She’ll be on the Sunday 2:00. Then we’re square” (53).

Chapter 7 Summary: “Itchy All Over”

The next morning, Moose wakes up from nightmares of his sister encased in ice. He finds strange, itchy welts all over his body, which his mother says are hives. Still, he marvels at how calm and peaceful the house is without Natalie and the “hubbub” that always surrounds her. He also enjoys being the center of his mother’s attention for once.

All the same, he knows that it is up to him to protect Natalie, which means not telling anyone about his deal with Capone. It disturbs him that Seven Fingers must be a friend of Capone’s, since the axe-murderer is often in his house. Moreover, he knows that handing roses to Capone’s wife on the ferry, in full view of the guards, could lead to his father getting fired. Nevertheless, he has no choice: After what Capone did for Natalie, Moose owes him a favor.

Chapter 8 Summary: “Icebox Fly”

That Thursday, with only three days left before Mae Capone’s arrival on the ferry, Moose’s hives are worse than ever. He still has no idea how he will get the roses, or how he can possibly deliver them to Mae without being seen. He decides to clear his mind by playing baseball with Annie, but when he gets to her apartment, she is not there. Mrs. Bomini invites him in, and Annie later arrives. Once outside with her, he says that he has resolved the Al Capone problem, and asks her to play baseball with him, even getting down on one knee to beg. Annie, amused by his submission, seems agreeable, but then goes back inside and shuts the door, exasperating Moose.

Determined to play baseball with someone, Moose goes to Bea Trixle’s canteen, where Jimmy works. Jimmy seems distant with him, perhaps still angry about the day Scout visited. Jimmy’s sister Theresa is also there, looking after their sibling Baby Rocky. Jimmy softens a little when Moose asks him about his pet flies; he shows Moose how he stores them in an icebox to make them slow enough to “harness” with braided thread. Meanwhile, Piper comes in.

Suddenly, Baby Rocky chokes on something Theresa has given him. Jimmy shouts at Moose to run the baby to Doc Ollie’s. Piper demands to take the baby instead, claiming to be “faster,” but Theresa shoves her against a wall. Moose sprints desperately with Baby Rocky, who has become quiet and still, to Doc Ollie’s office. With his forceps, the doctor probes into the baby’s throat and removes a Lincoln-head penny. Rocky, out of danger, begins to howl.

Chapter 9 Summary: “That Your Boy, Boss?”

The crisis over, Moose realizes that he is standing in the cellhouse, home to the country’s most dangerous convicts. As a reward for his heroic actions, his father and Doc Ollie give him a partial tour of the cellhouse, which ends at the cell of Capone himself.

The beefy Capone, his scarred face graced with a charming smile, interrupts his work—shining a pair of Darby Trixle’s shoes—to greet them. With a wink, Capone offers to shine Moose’s and his father’s shoes as well, but Cam coolly declines. Capone asks if there are any plans to give him a “roommate,” saying he prefers his solitude. When Cam says it’s out of his hands, Capone suggests that any man can make things happen if he tries hard enough, citing himself as an example. Cam scoffs that things haven’t worked out too well for him lately. Capone tells Moose he has a job waiting for him when he gets out, and that he looks like the “kinda person who keeps up his end of a deal” (71). Sternly, Cam ends the visit. As his father leads him away, Moose hears the mobster whisper, “Bye, son.”

Chapters 1-9 Analysis

Growing up on Alcatraz Island forces Moose to live in close proximity to some famous convicted felons—most notably, Al Capone (See: Background). The book’s prison setting and Moose’s dealings with Capone himself introduce the theme of The Nature of Celebrity and Notoriety. In the series’ first novel, Moose asked Capone for a favor for his neurodivergent sister, Natalie. Moose hoped that attending the Marinoff School would help Natalie manage her autism and thus help the family as well. Capone answered Moose’s request, and Moose’s sense of obligation toward the gangster now drives the central conflict of Al Capone Shines My Shoes. When Moose receives an ominous note from Capone stating that it is now his “turn,” he becomes nervous at the idea that Capone may demand a favor he cannot fulfill.

Capone is a shadowy figure whose aims are mysterious and whose actions are unpredictable. Capone’s characterization is complex: While Moose knows about Capone’s past as a violent crime boss, Capone also comes across as charming and attractive in other ways. When Moose visits Capone in his jail cell during the tour, Capone offers to shine Moose and Cam’s shoes, which helps him to appear friendly and even humble. There is, nevertheless, a threatening undertone to the interaction, with Capone’s hints about how a man can make anything happen if he tries, and his offer of a “job” for Moose when he gets out, reminding Moose of Capone’s power and influence. In a similar manner, his remark about Moose looking like someone “who keeps up his end of the deal” is an indirect way of reminding Moose that he owes Capone a favor (71). As they part, Capone calls him “son,” suggesting a degree of familiarity. Capone’s attitude and behavior are thus both charming and manipulative, which complicates Moose’s feelings about him and makes it harder for Moose to determine how best to handle his interactions with Capone.

Capone’s dangerous reputation increases Moose’s fear and tension, as he does not know what will happen if he does something to make Capone mad. Moose’s dilemma introduces the theme of The Dangers of Moral Compromises. As Annie warns, there may be no way out of his dilemma: If he refuses Capone’s request, the gangster may have him killed; if he grants it, the authorities may find out and fire his father. Moose is also reluctant to refuse Capone’s request because he believes that Natalie is benefiting from her schooling: His mother reports that she is doing really well, and Moose feels it is his responsibility to help his sister. In asking his dad if he has ever done “the wrong thing for the right reason” (52), Moose hints at the nature of his own dilemma: His intentions in asking for Capone’s help were the “right reason,” as he was trying to do a good deed for his sister. However, his current dilemma reminds Moose that getting involved with Capone is the “wrong thing” because Capone is dangerous.

Moose’s pact with Capone also threatens his close friendship with Annie, who loses some respect for him when she finds Capone’s note in his laundry. Their argument introduces the novel’s third major theme, Friendship and Trust in Challenging Settings. Annie’s anger exposes an unspoken tension between them: She has never really believed that Natalie’s condition can be treated, and so derides Moose for needlessly endangering himself on his sister’s behalf. Annie’s disrespectful attitude toward Natalie hurts Moose’s feelings and puts a strain on their friendship, increasing his sense of worry and isolation. When Scout visits, Annie encourages him to shut Moose out of their baseball game, which is extra hard for Moose because baseball is his favorite distraction from his many worries. Meanwhile, Scout’s charm and baseball skills also make Jimmy jealous, as he fears that Scout may replace him as Moose’s best friend. As the novel progresses, Moose will have to address both his dilemma with Capone and some of the problems facing his friendships.

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