Al Capone Does My Shirts by Gennifer Choldenko


  • Title: Al Capone Does My Shirts
  • Author: Gennifer Choldenko
  • Publisher: Putnam Juvenile
  • Year Published: 2004
  • ISBN: 0399238611
  • List Price: $17.99
  • Page Count: 240
  • Age Range: 10-14 yrs
  • Genre: historical fiction
  • Award(s): Newbery Honor;
    School Library Journal Best Book of the Year; other awards listed here.

Author information: Al Capone Does My Shirts is the most famous novel by Gennifer Choldenko. Her website includes information about herself, upcoming tours, advice for writers, resources for teachers, and additional information about Alcatraz, Al Capone, and autism. An interview with Choldenko can be found here, in which she talks about her family, writing and publishing, and her research for the Al Capone books.

Readers annotation: Moose Flanagan’s family just moved to Alcatraz, home of the worst criminals in the country, and he is not happy about it.

Reviews: School Library Journal and Booklist both gave this novel positive reviews (accessible here). SLJ says that “the Flanagan family is believable in the way each member deals with Natalie and her difficulties, and Moose makes a sympathetic main character”, and Booklist also praises the novel’s well-developed characters. Both reviews also highlight the unique setting of the novel as an appeal factor of the book.

Summary: Moose Flanagan thinks his life is ruined when his parents move him from his home in Santa Monica to the island of Alcatraz, where the country’s worst criminals are kept. One of the reasons for the move is because the island is close to a special school that his parents hope his autistic sister, Natalie, will be able to attend, but after only one night there they are informed that she is not a good fit for the school and must return to live with her family. This means that Moose has to take on many of the responsibilities of taking care of her, including watching her during the day and letting her tag along when he spends time with friends. Further complicating his life is his new classmate and daughter of the Alcatraz warden, Piper, who concocts a variety of schemes that are sure to get Moose in trouble. As the novel progresses, Moose makes friends and adjusts to life on the island and Natalie’s social skills improve drastically. At the end of the story, she is admitted into a new school for older children, potentially as a result of Al Capone using his connections.

Evaluation: This book approaches the relationships between its characters with heart and honesty. Choldenko does not shy away from presenting difficult truths, such as Moose’s challenging and often uncomfortable relationship with his mother, his sometimes burdensome duties towards his sister, and the economic realities his family faces. The treatment of these subjects allows the reader to sympathize with Moose and makes him a character that readers are rooting for. Setting this story against the backdrop of Alcatraz Island works wonderfully, as the setting does not overwhelm the narrative but rather complements it by adding enriching historical detail and opportunities for plotlines. Some of the action centering around Alcatraz as a setting does get a bit cute and contrived–it’s difficult to believe that Al Capone would slip a note into Moose’s shirt or that a few kids could launder an entire classroom’s worth of shirts–and these moments are the weakness in an otherwise enjoyable book, and the reader will easily suspend disbelief for these plot points due to the power of the narrative voice and the tenderness of the relationships portrayed in the novel.

Rating and appeal factors:

  • Quality: 3/5  The portrayal of the relationship between him and his sister as well as his family dynamic are the strengths of the novel. However, many of the plot points seemed contrived and stretched believability.
  • Popularity4/5  This novel is fast-paced and Moose’s voice is engaging and relatable. Although the book looks at a serious topic, there are moments of humor and friendship to lighten the mood. Readers who pick up the book because of the title may be disappointed, as the title leads one to believe there may be more gangster action than there is.
  • Appeal factors: Serious subject matter that is dealt with in an uplifting way, themes of acceptance, responsibility, family, and friendship, strong and sympathetic narrative voice, and local appeal for Bay Area residents.


  1. Holes by Louis Sachar would be a good recommendation for fans of this book, because they both feature a strong male protagonist with a unique voice who is struggling with difficult situations. Readers who enjoyed the antics of Moose’s friends on Alcatraz will similarly enjoy reading about the characters of Camp Green Lake. Holes also has a happy ending, which will satisfy those who appreciated how nicely things wrapped up in Al Capone.
  2. For those who enjoyed reading about Moose’s relationship with Natalie, R. J. Palacio’s Wonder may be a good fit. This book follows August Pullman, who was born with a facial deformity, and his experience going to school and making friends for the first time. The themes of friendship and acceptance echo those found in Choldenko’s novel.

Book talk ideas: Raise your hand if you have ever visited Alcatraz. Now, can you imagine growing up there, while criminals were living right next door to you? That’s exactly what happens in this book. Discuss briefly the plot of the book, and potentially bring up some fun facts about Alcatraz and some of the colorful inmates (like, of course, Al Capone), who resided there.

Discussion questions/ideas:

  • Describe Moose’s relationship with his mother. Why do you think they struggle to get along?
  • In what ways do the main characters–Moose, Natalie, and Piper–change over the course of the novel?
  • Why do you think Natalie was admitted to Mr. Purdy’s new school?

Reason for reading: I’ve seen Al Capone Does My Shirts on reading lists for years, but something about the title made me think that it was going to be a little too cutesy and light for my interest. I decided to pick it up the other day because my library had a display of award winning youth literature up because the Caldecott and Newbery awards were recently announced, and I decided it wouldn’t hurt to give it a try. I was interested in the idea of a book told by the perspective of a child who lives at Alcatraz–as a Bay Area native and a current SF resident, I will say that I’m a sucker for books with local settings–and after the first chapter I was hooked and couldn’t put it down.

Additional relevant information: There are two other books in this series, Al Capone Shines My Shoes, and Al Capone Does My Homework. Gennifer Choldenko’s sister suffers from autism, which accounts for the deeply personal and tender way Moose and Natalie’s relationship is portrayed. She is also a Bay Area resident.


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