Al Capone Shines My Shoes

Sixteen-year-old Natalie Flanagan is Moose’s sister, who has autism. The Flanagan family accepted the post on Alcatraz Island so that Natalie could attend the Esther P. Marinoff School, and Moose asked Capone for help in getting her accepted there. Moose’s obligation to Capone for this favor drives much of the story’s action.

Natalie’s neurodivergence further complicates the family’s status on Alcatraz, where she is viewed by some as a security risk. After being manipulated by an ex-con, she carries a jailbreaking tool onto the island—an action that, if discovered by authorities, could have led to her father’s dismissal. The guard Darby Trixle believes that Natalie should be put away in a home and never be allowed to mingle in public. Natalie’s immediate family is among the few who recognize her intellectual powers, which include an extraordinary facility for numbers and an acute memory for objects, rules, and events. As Moose observes, “Sometimes Nat is smarter than we are” (5).

Toward the novel’s end, Natalie demonstrates her unique abilities when she identifies her abductors’ guns as fake and then traces the location of a missing baby by following a convict’s pet mouse. In so doing, she helps save the day—which helps the people of Alcatraz recognize her intelligence and her innate value as a person.

Moose’s father Cam is a prison guard and electrician at Alcatraz. He is compassionate, brave, and deeply conscientious. As he tells Moose several times throughout the novel, truth is all-important, and doing the “right thing” will always protect them. Moose sometimes doubts this, but his father is clearly the model for his own moral compass.

Cam has also taught his son to give others the benefit of the doubt, and to treat people with courtesy and respect—even prisoners, who he thinks behave better if treated well. In this, he differs from Darby Trixle, whose notion of “rehabilitation” is brutally punitive. Darby, for his part, regards Cam as “soft,” but this is a misunderstanding. Although soft-spoken, sensitive to others’ feelings, and understanding almost to a fault, Cam has inner reserves of toughness and courage, such as when he interrogates Capone in his jail cell.

Al Capone was an Italian American gangster who built an underworld empire throughout the 1920s, largely on the illegal sale of bootleg liquor and the brutal murder of competitors. In 1931, he was convicted of income tax evasion and sentenced to 11 years in federal prison, more than four years of which he eventually served at Alcatraz (See: Background).

In Al Capone Shines My Shoes, Capone represents The Nature of Celebrity and Notoriety. His legendary menace shows itself only in subtle ways, such as in brief messages left in Moose’s newly-washed laundry or by spitting into Eliot Ness’s food while serving as a server. Though confined to a five-by-nine-foot cell, Capone still wields a great deal of power both in Alcatraz and beyond. He proves his power by arranging Natalie Flanagan’s acceptance by the Esther P. Marinoff School in San Francisco. Moose fears what Capone will do if Moose does not fulfill any favor asked of him in return.

In Moose’s two encounters with Capone at his cell, the latter displays a ready wit and a sly charm, but Moose’s father cautions him not to be taken in: With Capone, he says, every favor or gift is transactional, and the last thing you want is to “owe” him anything. Regardless, Capone does reveal a sensitive side: His “payback” is simply for Moose to give his wife yellow roses. When the warden’s newborn son is briefly abducted and brought to him, Capone shows his fathering skills, cradling the baby expertly in his arms. As the most notorious of Alcatraz’s inmates, the slippery Capone must placate both the authorities and his fellow prisoners, without tipping the scales too far either way.

Alcatraz prison guard Darby Trixle is the main antagonist. He is an important contrast to Cam Flanagan. Where Cam is polite and soft-spoken, Darby is boorish and loud; where Cam is compassionate and tolerant, Darby is callous, suspicious, and sexist; where Cam is sensitive and good-humored, Darby is humorless, vindictive, and threatening. Darby, says Moose, is “the kind of guy who only his wife likes—and not that much either” (2).

In the first scene of the novel, Darby deliberately panics Natalie by spraying the bay with gunfire. This act establishes his spiteful, unfeeling character, which does not change significantly throughout the book. He is a cold father toward Piper because he only wants to have a son, and he openly neglects his very ill wife. Darby believes in treating the prisoners harshly and asserts that Natalie should be sent away permanently, the way Darby’s own brother was. His animosity toward Natalie, and thus toward the whole Flanagan family, creates tension in the story, since he is always looking for a pretext to have them thrown off the island.