53 pages • 1-hour read
Al Capone Does My Homework
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Character Analysis
Moose Flanagan
Thirteen-year-old Matthew “Moose” Flanagan, the novel’s protagonist and first-person narrator, lives on Alcatraz Island with his sister, mother, and father, who is the associate warden of the Alcatraz prison. Tall for his age, Moose has a powerful throwing arm, which comes in useful in the story when he disarms a knife-wielding con with an expertly aimed baseball. Matthew deals with more pressures than do most boys his age since he worries constantly about his father, who he thinks is “too nice” to be a warden—especially of Alcatraz, one of the “roughest” prisons in the country. Accordingly, he begins to test himself, showing his courage by confronting dangerous adults who threaten his family, including the convict Indiana and the guard Darby Trixle. Added to this, his older sister Natalie has a developmental disorder that requires constant attention, and he devotes much of his time to both protecting her and trying to make her more independent. These latter efforts prove a source of friction with his mother, who sometimes feels he is pushing Natalie too hard to engage with the outside world. Moose’s worries come to a head when his family’s apartment burns down, for which he does not know whether to blame Natalie (and therefore himself, as he was supposed to be watching her) or some unknown person who may be targeting his father. Simultaneously, he finds himself navigating a romantic triangle with two neighbor girls (Piper and Annie), each of whom attracts him in different ways. In the end, he saves his father from a deadly attack, and Natalie’s budding independence and perception vindicate his faith in her. He also solves a mystery involving Piper that resolves his romantic dilemma.
Natalie Flanagan
Natalie (or “Nat”), Moose’s 16-year-old sister, in her father’s words, “views the world through her own private kaleidoscope” (2). Based on the author’s sister, who had autism, Natalie has an undiagnosed developmental disability; she demonstrates certain fixations and compulsive behaviors that lead some neighbors to regard her with prejudice, though she also shows remarkable mental abilities, especially in the field of math. One of her habits, the continual flicking of light switches on and off, convinces Moose that she could not have accidentally started a fire in the kitchen, as some of the neighbors believed. Her extraordinary talent for counting exposes Donny Caconi as a card cheat, leading to his arrest for smuggling counterfeit money. Despite her abilities, Natalie is widely misunderstood by the other residents of Alcatraz, partly because she seems aloof and confused and because she resists making eye contact. However, her family knows that she sees and understands much more than others realize. Late in the story, when her father is injured, she insists on visiting him at the city hospital and resoundingly justifies Moose’s faith in her when she successfully displays neurotypical actions (that others coached her on) as she checks in at reception.
Donny Caconi
Donny, the slippery antagonist of Al Capone Does My Homework, is the adult son of Mrs. Caconi, the wife of a former Alcatraz guard. Supposedly in the “trucking” business, Donny visits the island a couple of days a week to get his laundry done for free. However, he is actually smuggling counterfeit money into the prison in his laundry bags. High-spirited, stylishly dressed, and as slim and “graceful as a girl” (5), Donny exudes a ready charm and has made himself well-liked at Alcatraz, particularly by Moose and his friends, who look forward to his visits. Moose’s opinion of him begins to change after Donny manipulates him into a money bet that he believes was fixed. The two-faced Donny owes money to a loan shark and will sell out any of his Alcatraz “friends” to raise the cash, including cheating at poker, abetting a counterfeiting scheme, and even setting fire to the Flanagans’ apartment with Moose and Natalie inside. It becomes clear that he will use anyone, even children, to work an angle. Even when out on bail for arson, he keeps on scheming, hoping to use Natalie’s card-counting abilities in his future scams. However, Natalie, immune to his surface charm, predicts his future, to his face, as Alcatraz’s next prisoner: number 317.
Darby Trixle
Nicknamed “Double Tough,” the bellicose prison guard Darby Trixle seems only slightly more trustworthy than the hardened cons he shouts at through his bullhorn. As Moose notes early on, Darby was born in a uniform that is “one size too tight” (2). A foil to Moose’s gentle father, Darby makes no secret of his festering resentment at being passed over for promotion, and Moose worries that he will take any opportunity to undermine his father’s authority. A believer in punishment rather than rehabilitation, Darby rationalizes his disloyalty to his new boss with the theory that the prison’s discipline will collapse under the compassionate leadership of Cam Flanagan. While going through the motions of obedience, Darby tries to embarrass Cam through his daughter Natalie, whom he and his wife accuse, without evidence, of starting the fire in the Flanagans’ apartment. According to Darby’s own daughter, he actually plotted the arson himself. Though he briefly shows some slight gratitude to Natalie for spotting Donny’s card grift and saving him “a bundle of money” (138), he continues to be coldly dismissive of her and of the kids in general.
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