Al Capone Shines My Shoes

The sequel to the Newbery-Honor winning Al Capone Does My Shirts, Gennifer Choldenko’s middle-grade historical novel Al Capone Shines My Shoes (2009), is the second book in her Tales from Alcatraz series. In this installment, first-person narrator Moose Flanagan, the twelve-year-old son of a prison guard on Alcatraz island, is alarmed when he learns it is his turn to do a favor for the legendary criminal Al Capone. As Moose navigates tricky relationships between friends, family, and new crushes, he also learns important lessons about self-reliance, honesty, and forgiveness.

Al Capone Shines My Shoes picks up where Al Capone Does My Shirts ends. It is August of 1935, and easy-going, affable, athletic Moose and twenty-four other kids—all children of prison guards and employees—live with their families in a residential building on Alcatraz. The prison is home to 278 of America’s worst criminals: the “Cream of the Criminal Crop.”

One of Moose’s favorite pastimes is baseball, which he firmly believes is “enough to cure anything bad that could ever happen.” His best friend, Jimmy, not good at baseball, doesn’t feel the same way about it. Instead, Jimmy focuses on breeding his flies, which he keeps in a little box made of folded newspaper, and attempts to teach them tricks for a fly circus. Annie is Moose’s other good friend. She has white-blonde hair and is a great pitcher in their games. Scout, Moose’s friend from the mainland, is “Mr. Baseball.” He puts Jimmy down and rubs Annie the wrong way when he classes her as an “auntie.” In Scout’s eyes, girls are either “lookers,” “okey-dokeys,” or “aunties.” Piper Williams rounds out the group of Moose’s friends. Piper, the daughter of the warden, is pretty, spoiled, and angry. Moose’s mother comments that Piper is twelve going on eighteen…and not a good eighteen.



Moose and his friends attend school on the mainland, play a lot of baseball on the island, and interact with some of the convicts who are passmen. Select, well-behaved criminals are allowed to work for the families: the ax-murderer, Seven-Fingers, for instance, helps fix plumbing. Con-artist Buddy Boy is Piper’s houseboy, and the thief Willy One Arm is Piper’s cook.

In the first novel, Moose asks Al Capone to pull some strings to help his autistic teenage sister, Natalie, get into a special school for the mentally ill. Capone comes through with the favor, and Natalie is accepted to the Esther P. Marinoff School for older children. Now, however, Capone wants a favor from Moose in return.

Capone, prisoner #85, works in the prison laundry and does washing for the guards’ families as well. One day, Annie gets Moose’s laundry by mistake and finds a note inside one of his shirts. The note reads “Your turn.” Annie is alarmed and asks Moose about it. Moose confides that he did ask Al Capone for a favor and is now in the criminal’s debt. Annie tells Moose that Capone is like a cat, and Moose is a mouse. Moose worries, too, so much so that he gets hives, but Capone’s favor turns out to be simple: buy some yellow roses for his wife Mae Capone. Moose gets the flowers, fulfilling his side of the bargain.



When Jimmy’s little brother Rocky, chokes on a penny, Moose saves his life by rushing the boy to Doc Ollie. As a reward, Moose’s father takes him to meet Al Capone, warning Moose that respecting the prisoner is different from trusting him. Capone has dark black hair, dark eyes, a round face, and “the kind of smile that makes you like him without thinking twice about it.” Moose shakes his hand through the bars. Piper is angry and jealous that Moose got to meet Capone. To get back at Moose, she lies to her father, saying that Moose’s and Jimmy’s dads were drinking before they went on guard duty. The two men are put on probation. Moose is upset.

Meanwhile, Natalie comes home to visit. When she unpacks her suitcase, Moose and Jimmy and Jimmy’s sister Teresa find a metal bar spreader which is used in prison breakouts. Natalie doesn’t know what it is, but Moose thinks a former convict, #105 gave it to her. Moose and Jimmy are aghast and plan to get rid of it.

The prison holds a formal dinner for visiting VIPs: famous law enforcement officials, Eliot Ness and J. Edgar Hoover. Al Capone is assigned to be a waiter at the dinner. Piper tells Moose she will get his and Jimmy’s dads off probation if Moose can sneak her in to see Al Capone. Moose agrees, and Piper apologizes to Jimmy’s dad and the people she hurt. Moose discovers that Piper has been acting so cruel because she has been worried about her mother, who is pregnant and very ill. Good news arrives from the hospital: both Piper’s mother and the baby are okay.



The Warden jubilantly returns to Alcatraz with his new son, Walter, and has a party to celebrate. Three prisoners take advantage of this distraction to escape. Trusted passmen Willy One Arm, Buddy Boy, and Seven Fingers take Moose, his friends, Natalie, and Piper’s new baby brother hostage. The men force the kids down to the dock, but Moose realizes that they are only pretending to have guns. He shouts for help, and guards recapture the prisoners. Baby Walter, however, is missing. Earlier, Willy One Arm took the baby away. Everyone searches for the baby, and Natalie finds him in Capone’s cell, safe and snug in the criminal’s arms. Capone knew about the breakout plan but refused to go along with it because he didn’t want to mess up his own release, scheduled in just a few years.

When life settles back to normal, Moose has an even greater appreciation for the unique qualities of his friends and the depth of their friendship.