Al Capone Shines My Shoes

“But out of desperation, I sent a letter asking Capone for help and Natalie got accepted. Then I got a note in the pocket of my newly laundered shirt: Done, it said.”

In the series’ first book, Moose confronts The Dangers of Moral Compromises: To get his neurodivergent sister Natalie into a special school that represents her best hope for the future, he asks one of the island’s convicts, the notorious mobster Al Capone, for help. Shortly afterward, the school unexpectedly accepts her, and Capone implies with his note that he is responsible. Moose knows that a man like Capone seldom does favors for free.

“Sometimes Nat is smarter than we are. Other times, she doesn’t understand the first thing about anything. That’s the trouble with Natalie—you never know which way she’ll go.”

Like many on the autism spectrum, 16-year-old Natalie focuses her attention and intellect in unorthodox and often unpredictable ways. As a result, she can be hard to manage sometimes—as when she smuggles a “bar spreader” onto the island—but she also notices things that Moose and others do not. This passage foreshadows Natalie’s crucial observation, late in the book, that the cons who have abducted her and Moose are carrying fake guns.

“The note is written on the same paper in the same handwriting as the other one. Your turn, it says.”

Moose’s fears are realized when he receives a note in his laundry, ostensibly from Al Capone, demanding a favor in return for the one Capone claims to have done for Natalie. Capone, though behind bars, still wields great influence in Alcatraz and beyond, and Moose fears the repercussions of refusing his request. He also dreads his family finding out about the request he made to Capone.

“My Mae loves yellow roses. She’ll be on the Sunday 2:00. Then we’re square.”

Capone’s next note specifies the “payback” he demands: to give his wife yellow roses as she arrives on the ferry. It seems a small request, but deceptively so—with so many guards watching, including the warden himself, it will require all of Moose’s ingenuity. Additionally, with a slippery character like Capone, there is probably something else afoot.

“You gotta watch the cons like him—the ones with brains. Starts innocent enough. He shines your shoes. Pretty soon, he wants something for his efforts. A stick of gum maybe. You gonna give it to him? Well, you owe him now.”

Moose’s father explains to him the ethical minefield he faces every day as a guard in Alcatraz, where the simplest interactions can be dangerous. His warning echoes what Annie told him earlier, that accepting a favor from someone like Al Capone is a no-win situation: Paying him back, even on the smallest scale, can put you under suspicion of bribing a prisoner. The irony is that Moose, unbeknownst to his father, has already accepted a big favor from the mobster.

“Jimmy snorts. ‘That’s right. Got to keep everybody happy, right, Moose?’”

Moose’s friend Jimmy puts his finger on an issue that complicates Moose’s life: the pressure he feels to make everyone in his life happy. Moose has long played peacemaker with his sister who has autism, and his family’s difficult situation in Alcatraz has led him to put out every possible fire before it can spread by seeking to please everyone. Sometimes this behavior offends his friends, notably Jimmy and Piper, who sometimes feel that he does not back them up against others.

“‘I wished Rocky would go away.’ She can hardly get these words out.”

After Rocky’s near-death by choking, Theresa stays alone for days out of guilt for having given her baby brother a coin to play with. As Moose tries to comfort her, she reveals a deeper source of her guilt: She sometimes resented Rocky and wished he’d go away. Moose consoles her by confessing that he’s had similar thoughts about his own sister Natalie, whom he deeply loves. This develops Moose’s complicated feelings about his sister, as well as his desire to keep the people around him happy.

“And then suddenly it occurs to me. If I give roses to every woman on the boat, I won’t get in trouble.”

On the Alcatraz ferry with Mae Capone, whom he has been told to give yellow roses, Moose has an idea about how to avoid the impression of doing the Capones a special favor. Capone, who likes testing people, might have given him this task partly to force him to use his wits.

“If you close your eyes, you’d swear you were listening to Shirley on the radio. Open them and Buddy almost looks like her too. It’s a little creepy.”

The “passman” Buddy Boy—a con artist who has been given work privileges at the warden’s house—is a master impressionist who can perfectly mimic the voice of six-year-old Shirley Temple. The “creepiness” of this ability foreshadows his later, sinister actions, such as his mimicry of Jimmy’s voice to lure Moose and Piper outside so they can be kidnapped.

“‘Dad’s on probation.’ He looks at me. ‘Your dad too. They got written up for being drunk on guard tower duty.’”

The pressure on Moose, who has had a falling-out with Piper and Jimmy, increases when his father is falsely accused, along with Jimmy’s father, of drunkenness on the job. Now the slightest infraction could get them fired. As usual on Alcatraz, Moose doesn’t know the source of this new trouble, whether it is one of the cons, a guard, or even one of the kids he knows. This crisis is quickly made worse when the kids discover a piece of contraband (a “bar spreader”) in Natalie’s suitcase.

“‘This ain’t kid stuff,’ he murmurs, the smell of bad breath and tobacco filling my nostrils. ‘We know where she sleeps.’”

Seven Fingers, a dangerous convict on work release as a plumber, threatens Moose through his sister Natalie, to try to pressure him to give up the bar spreader. Moose does not know whether the cons can get into her bedroom at Alcatraz or her boarding school in the city, where Moose cannot protect her. He cannot tell his father, who is on probation, because Natalie’s smuggling of the bar spreader might get him fired.

“Her life isn’t gonna go the expected way. But just because she doesn’t see the world like you and me doesn’t mean she isn’t getting just as much out of her days as we do. Who are we to say what life’s supposed to be about, Moose?”

Moose’s father shares his perspective on Natalie’s autism, which he sees as an equally rich and valid, way of experiencing life. His and Moose’s belief in her as a complex human being as worthy of love and respect draws a sharp contrast with the guard Darby Trixle, who tells Moose that his own family made a ”clean break” from his brother, who “wasn’t right in the head” (201).

“Like I said this afternoon, Mr. Hoover, we have the cleverest criminals in the whole country here on Alcatraz. I think it would be a bad idea to cut back our guard forces…a bad idea indeed.”

Alcatraz’s warden, who has arranged to have J. Edgar Hoover, the head of the FBI, pickpocketed by a felon, spells out the moral of his little stunt. In this and other actions, he shows himself to be a bully and manipulator, who has little use for subtlety or other social graces.

“‘So you never visit. Ever,’ I whisper. […] ‘You just move on from the bad things. You understand me, boy.’ […] ‘She’s not a bad thing,’ I whisper.”

Moose is shocked to hear that Darby Trixle’s brother has spent most of his life in a home, and that Darby has never visited him. Darby implies that Moose’s family should do the same with Natalie. His attitude, besides illustrating common perspectives of the time, underscores his difference from Moose’s father, who believes in helping others and treating everyone (including convicts) with respect.

“‘I wanted It Ee-it to die. Not my mom.’ Her voice catches.”

Piper, like Theresa in an earlier scene, confesses to Moose her jealous thoughts about her unborn sibling, even wishing for its death. Also like Theresa, this has led to terrible feelings of guilt once something went wrong—in her case, her mother’s near death in childbirth.

“‘A boy! It’s a boy!’ he crows, handing out cigars to every man getting off the boat, no matter his rank.”

Piper’s father, who has been “hankering” for a son for 20 years—long before his daughter’s birth—finally has his wish and seems largely unconcerned about the fact that his wife nearly died. His selfishness and sexism hint at the roots of Piper’s own angry behavior, as well as her loneliness and feelings of injustice. When she tells Moose that it’s “not fair” that boys get more attention than girls, she reveals her sense of being ignored and unloved; this could explain her attempts to level the playing field with her lies and other schemes.

“‘He’s not here. You go back. I’m going to take Nat home,’ I tell Piper, changing course under Piper’s window, when suddenly something clammy and cold closes around my neck, crushing my throat. […] ‘Shut it,’ a voice whispers in my ear, ‘or you die.’”

Buddy Boy, the passman who does impressions of Shirley Temple and others, pushes the narrative to its final crisis when he and two other cons abduct Moose, Piper, and Natalie as part of an escape attempt. Buddy has used his skills to lure the children outside by imitating Jimmy’s voice, proving Moose’s claim in the novel’s opening lines that in Alcatraz, nothing is as it seems.

“‘How’d you do that, Buddy?’ I ask, my voice hoarse because of how tightly Seven Fingers is grasping my throat. ‘Make your voice sound like Jimmy?’”

Held around the throat by a convict and threatened with death, Moose outsmarts Buddy Boy by playing on his vanity, coaxing him into mimicking Jimmy’s voice again. Buddy happily obliges, and the real Jimmy, his sister, and Annie hear him and know that something is amiss.

“If I’m wrong, we could die. […] But Natalie’s never wrong. Not about counting. Not ever.”

Natalie, fascinated with objects and especially numbers, counts the convicts’ arms (five, since one of them is one-armed) and their guns, of which there are “zero,” she says. As Moose realizes, she has noticed something no one else could: The convicts’ guns are fake, probably carved out of wood. Putting his faith in his sister’s extraordinary abilities, he shouts to the guards that the kidnappers have no guns.

“Piper is ranting, her words slur. She grabs hold of my dad. ‘He’s my brother. I have to find him.’”

Piper, who earlier confessed to wishing her new brother was dead, shows that her feelings of jealousy and bitterness go no deeper than Theresa’s or Moose’s sporadic anger at their own siblings. When the baby is carried away by a fleeing convict, her love comes to the surface; unlike when Baby Rocky was choking, her thoughts are no longer of one-upmanship but of desperation for her brother’s life.

“Piper’s little brother—the tiny baby—he’s here. Capone has him in his arms.”

In an unexpected twist, the fearsome mobster Al Capone holds the missing baby in his arms. This development and others show some similarity between Al Capone and Moose Flanagan, both of whom continually perform a sort of balancing act to keep the peace at Alcatraz. Just as Moose tries to soothe his friends’ fears, Capone helps his fellow cons as much as he needs to, while helping the authorities at the same time: Refusing to inform on his friends, he looks after the warden’s son, and hands him back unharmed. Whatever his motives, this Capone is a more complex figure than he is often represented.

“If I open my mouth, I’m putting Natalie in jeopardy. But I wasn’t brought up to let someone else take the blame for something he didn’t do, even if it is a nitwit like Darby Trixle.”

Through his honesty, Moose shows the differences between himself and Piper, when he confesses to his father that Darby, whom he hates, did not smuggle in the bar spreader that was discovered in the Trixle house. Whereas Piper, purely out of spite, falsely accused her friends’ fathers of drunkenness on the job, Moose refuses to allow Darby to take the blame for others’ mistakes—even though revealing Natalie’s involvement may jeopardize his whole family.

“I saw how much I want to get along. But sometimes you have to make trouble. Sometimes making trouble is the right thing to do.”

Moose usually tries very hard not to rock the boat or to draw attention; at the first sign of trouble, he seeks to calm the situation with a soft answer. His need to keep everyone “happy” has even annoyed some of his friends. Sometimes, however, loudness and violence can be necessary, even lifesaving. Had he and his friends and sister not fought back against the cons, their story might have had a very different ending.