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93 pages 3 hours read

Al Capone Does My Shirts

Fiction | Novel | Middle Grade

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Character Analysis

Moose (Matt) Flanagan

The protagonist goes through remarkable growth and maturation over the course of the story. At the beginning of the novel, he is self-absorbed and miserable in his new surroundings and speaks of his intellectual disabled sister, Natalie, in not-so polite terms. His main focus is on the injustice of his situation. However, it is clear from the start that he is a responsible kid who follows the rules, and that he deeply loves his sister.

Because of his family’s financial circumstances, Moose must care for his sister. By including her in their daily activities, Moose makes Natalie a part of his friend group and all of this extra time with her allows him to see things from her point of view. He becomes more concerned for her wellbeing, even speaking out to his mom and breaking the rules of no contact with prisoners by writing Al Capone a letter to try and help Natalie. His special relationship with his sister proves that he can empathize with others and he becomes less self-centered as the novel goes on.

Natalie Flanagan

Although the novel never specifies her condition, which would not have been diagnosable in the 1930s, Natalie seems to be on the autism spectrum. Although she can communicate to some extent, Natalie cannot express her emotions or thoughts the way most people can. She sometimes suffers severe emotional outbursts and can become catatonic. She has a strong affinity for certain things, namely buttons and rocks, lemon cake, counting, and indexes, and this makes her unique. Rather than removing these obsessions from her life—as Helen was directed to by Mrs. Kelly—Moose allows Natalie to engage with them because it brings her contentment, much like baseball does for Moose. Natalie’s growing relationship with Moose allows her to express her individuality. Eventually, she begins to express herself more fully, refers to herself in the first person for the first time, and even forms a friendship with a stranger—a prisoner on the island—which suggests that she is capable of more than what her family expects of her. Moose convinces their mother to treat Natalie as who she is, to tell the truth about Natalie’s age rather than cling to a fiction that she will always be 10 years old, and stop trying to “fix” Natalie instead of supporting her development in a real and substantive way. 

Helen Flanagan

Moose and his mother Helen have a tense relationship, largely as a result of how she treats her children. All of her focus seems to be on “fixing” Natalie and all of their family’s major decisions, including moving to Alcatraz Island, revolve around this goal. Because of her intense focus on Natalie, and her assumption that Moose will turn out fine in comparison, Helen understandably does not devote nearly as much time to her son as to her daughter. The main points of contention between Moose and Helen are Moose’s feelings of being neglected and his assumption that his mother would rather be unrealistically optimistic—to the point of dishonestly—than see Natalie as she really is. By the end of the novel, Helen changes her perspective on Natalie, prompted by Moose’s strong rejection of Helen’s perpetual self-delusion that the family can treat Natalie as a permanent 10 year old.

Cam Flanagan

Moose’s father Cam is not around much for Moose because he works many hours to provide for the family financially—all the more so now that they are hoping to enroll Natalie in a special private school for the intellectually disabled. Moose feels more connected to his father than to his mother because Cam sees Moose for who he is—a good kid with concern for others. Cam is in a difficult position, however, because he also wants to support his wife and Natalie and so he abides by Helen’s plans for their daughter to keep the domestic peace. At the same time, he can see Moose’s legitimate concerns and hurt feelings. Cam is finally able to stand up to Helen and assert Natalie’s individuality and her real age near the end of the novel.

Piper Williams

The daughter of the Warden of Alcatraz Island is a troublemaker with a mischievous and manipulative nature. She is also an attractive girl and Moose is drawn to her in spite of himself. As the daughter of the Warden, Piper has the “power” to convince her father to fire their fathers from Alcatraz—a power she uses to enlist the other kids’ help in her moneymaking schemes. As the novel goes on, however, Moose pays less attention to Piper and she seems to become more kind. At first she was incredibly rude to Natalie, but at the end of the novel she wishes her a happy birthday. Rather than mocking the Flanagan family for lying about Natalie’s age, she keeps quiet out of respect even though she admits to Moose near the end of the novel that she is part of a “we” that knows Natalie is not ten. Ironically, all her attempts of connecting with the prisoners fail, while Natalie and Moose are able to connect with #105 and Al Capone. This might suggest that it is not through manipulation that we can reach out to people, but by connecting with their shared humanity.

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