Al Capone Does My Shirts

by Gennifer Choldenko

Al Capone Does My Shirts

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Book Information

Publication Date: April 20, 2006

Reading Level: Lexile Measure 600L, Scholastic Guided Reading Level X

Interest Level: Grades 6 - 8

Major Awards: Newbery Honor and California Young Reader Medal

Number of Pages: 241 pages

Approximate Word Count: 53,505 words

Audible Book Length: 6 hrs and 10 mins

Book Themes: Coming of Age, Brothers and Sisters, Friendship, History, Autism

Genre: historical fiction novel for young adults

Setting: on Alcatraz Island near San Francisco in 1935

Important Quote: “Nobody knows how things will turn out, that's why they go ahead and play the game...You give it your all and sometimes amazing things happen, but it's hardly ever what you expect.”

First Line: Today I moved to a twelve-acre rock covered with cement, topped with bird turd and surrounded by water.

Point of View: Author Gennifer Choldenko writes in first person point of view as if the book is a journal written by the main character, Moose Flanagan.


Discussion Questions

Scholastic Literature Circle Questions

Shmoop Al Capone Does My Shirts Questions

Vocabulary List

Chapter 1 Devil’s Island

The convicts
we have are the kind other prisons don’t want.
A full moon cuts a white path across the bay while the wind blows, making something creak and a buoy clang in the distance.

This is the dock guard tower, a popcorn stand on stilts where somebody’s dad sits with enough firepower to blow us all to smithereens.

The only guns on the island are up high in the towers or the catwalks, because one flick of the wrist and a gun carried by a guard is a gun carried by a criminal.

When I was five, I was kind of a runt. Smallest kid of all my cousins, shortest kid in my kindergarten class and on my block too.
“I’m having a devil of a time setting up extra circuits in the laundry.”

Okay, that’s it. I’m sleeping with my clothes on. Who wants to face a convicted felon in your pajamas?

Chapter 3 Trick Monkey

“First, we’re going to the morgue,” Theresa announces with a little skip.

Now we’re at a complete standstill on the steep road that leads to the top of the island. “Couldn’t we do this after the morgue?” I ask.
Favorite word for murder: “Rub-out”—often in front of many witnesses who then develop “gangster amnesia."

Sent to jail for: Tax evasion.

“Make a beeline there, Theresa. You know the rules.”

Chapter 4 American Laugh-Nosed Beet

“This new school is a good opportunity for you, Natalie,” my mother tells her as I watch the boat guy unwind a rope, as thick as my arm, from the cleat.

Chapter 5 Murderers Darn My Socks

“Put her in an asylum, Helen. It’s the humane thing to do,” Mrs. McCraw said between bites of cinnamon nut cake.

My mom turned ashen.

You’ll always win, but it will make you feel like a louse.

Chapter 6 Sucker

“When convicts first arrive on Alcatraz, I speak with them personally. Let them know what I expect. I don’t usually talk to new civilians, but Piper felt I should make an exception in your case,” the warden says.

I know my father says that in the event of a break the warden wants the guard corps within walking distance of the cell house.

Women are not to wear bathing suits, shorts or any attire that is anything but completely modest. Undergarments are not to be sent out with the laundry.”

Here on Alcatraz he’s a number like every other con. The point of this prison is to keep these showy criminals out of the limelight.

Chapter 7 Big for Seventh Grade

And now if I don’t talk about Alcatraz, I’ll look like a chump.

“No.” I make a scoffing noise like this is the silliest thing I ever heard.

Chapter 8 Prison Guy Plays Ball

“Only snacks. Snack time is with murderers. Suppertime is reserved for con men, counterfeiters and armed robbers.”

No clobber to a bat like that and the swing is faster than I like.

Third batter wallops one hard right to me.

Chapter 9 Nice Little Church Boy

“Yes, you do.” She nods, her whole face earnest.

“Shucks,” Jimmy says, his head low over his contraption again.

“Charm school? That’s a laugh. Is it remedial charm or what?”

Chapter 10 Not Ready

“How do I look?” She whirls around, her whole face radiant.

Chapter 11 The Best in the Country

They tested allergies, reflexes, muscle strength.

“Natalie is, I would say, unresponsive.”

It’s a fine residential neighborhood, but perhaps not an ideal spot for someone like your daughter . . .” His voice trails off.

“We can’t have a child who screams like a banshee at five-fifteen in the morning in a neighborhood like this.

She is seated on a needlepoint brocade chair and I see by the way her finger is moving that she is counting the stitches in the seat.

Chapter 12 What about the Electric Chair?

The fog’s in and everything is gray. The foghorns bellow deep low notes.

The cabin is empty except for two guards and a scrawny little man in a suit.

All Clothes Cleaned on Alcatraz at the only laundry facility in the world run by Convicted felons including the notorious Scarface Al and Machine Gun Kelly! Only Costs 5 Cents.

Solitary confinement.”

When we are all settled in our seats, Miss Bimp starts rattling on about the importance of good posture and how no cultivated lady or gentleman would dream of slumping during oral reports the way certain members of this class are doing.

Chapter 13 One-woman Commando Unit

Throw away Nat’s button box. They’ll be no more counting for her. No more obsessions.

She spent all afternoon with her,” my mom says, and then natters on about how Nat’s not supposed to count.

My mother’s voice has softened. There’s a wheedle in it now.

I stare at her. Suspicious now.

You know how your dad’s always saying the ratio of inmate to guard is three to one here compared to ten to one at San Quentin, which makes Alcatraz a much safer prison.

Chapter 15 Looking for Scarface

The fence is maybe twelve or fourteen feet high with three strands of barbed wire run across the top.

Chapter 16 Capone Washed Your Shirts

She walks right into the home economics room and unlocks the supply closet.

“I’m conducting business here.”

Chapter 18 Not on My Team

He says you’re a lot more coordinated than you look.

Chapter 19 Daddy’s Little Miss

The wind blows the eucalyptus trees, a buoy clangs, a boat horn toots, Natalie drags her toes.

But when he explained the details of the operation, I began to see that the idea was simply too preposterous to have been made up.

It’s bad enough that the great city of San Francisco should suffer the indignity of a maximum security federal penitentiary in its midst without being subject to these sorts of sick and dangerous shenanigans.

I am appalled by the extremely poor taste and unseemly behavior of your daughter and her friends.

Out of courtesy to you and your long and distinguished association with my brother, Judge Thomas Thornboy, and the San Francisco Rotary Club, I am addressing this letter to you in confidence. But if I should hear anything of this nature again, my next letter will go directly to the San Francisco Chronicle and the mayor’s office, respectively.

Well, fine. I’ll handle this like I would an uprising in the cell house.

“Even me?” Theresa’s voice is quavering.

Chapter 20 Warning

Apparently he knows the kind she likes, because Natalie seems to give these stones a special place in her elaborate grid.

“I won’t have her made a spectacle.”

Part Two -- Chapter 21 It Never Rains on Monday

But with no one to play with, it hasn’t done me a whit of good.

Chapter 22 Al Capone’s Mama

She’s pretty possessive about him.

And then out of the cabin comes Theresa carrying a howling baby wrapped in a blue crocheted blanket.

She’s the old Italian woman with a big ruddy face and white-gray wavy hair.

And try as she might, Mrs. Mattaman could not convince the terrified Mrs. Capone that this humiliation was the last.

Chapter 23 She’s Not Cute

I shimmy up the steep hill sideways and begin picking through the thicket of bushes. I try to walk in a pattern.

She’s setting them up, almost like an abacus. I wonder what she’s doing.

Chapter 24 Like a Regular Sister

The hill is steep and slippery with rocks and shale, land sliding down as I go up.

Chapter 25 My Gap

It’s a warm, clear spring day. I feel happy, as if I’m on the verge of something wonderful.

She’s very diligent about this, like it’s her job.

Chapter 26 Convict Baseball

Inmates aren’t allowed hair pomade.

“Hey, Moose.” The con’s voice is scratchy and an octave too high, like a girl’s almost.

Chapter 27 Idiot

My mouth tastes like curdled milk.

She tries to twist her arm away, but I’m not about to let go. Ever. She balks. Stops. Refuses to be half-dragged when we both know she follows just fine without this. But I won’t give her even this much freedom.

I’m not a ventriloquist and Natalie isn’t my dummy, but today I want her mute.

Chapter 28 Tall for Her Age


Chapter 29 Convict Choir Boy

“I think she’s googly-eyed for you, anyway,” he says.

Plus, the guy—they call him Onion because the way his hair is greased down makes his head look like an onion—he’s put together a whole slew of good time. He’s like some kind of Boy Scout choir boy.”

Chapter 30 Eye

Not one critical word comes out of her mouth.

She lays shaking, grateful and forlorn in the stained red carpet.

Chapter 31 My Dad

I set my beer by his and get the broom. The room is silent except for the clock ticking on the mantel, the sund of sweeping and the clink of china pieces as my father drops them in the metal trash tin.

Part Three -- Chapter 33 The Sun and the Moon

It’s Piper, her hat in her hand. An odd attitude for her.

She looks too vulnerable. Teetering on the edge.

Chapter 34 Happy Birthday

The smile on her face is the one she uses when parents of an obnoxious piano student ask how he is doing.

I go in my room and don’t come out until supper, which I wolf down without saying a word and then return to my room.

And from my mother a book bag with NATALIE FLANAGAN, THE ESTHER P. MARINOFF SCHOOL embroidered on the front.

Chapter 36 Waiting

This has to be the biggest understatement in the world.

I am seething inside. I open my mouth to tell her how wrong she is, how unfair she’s being.

She is just cutting into the lemon meringue pie when we hear the knock.

Chapter 37 Carrie Kelly

There’s a real bias against older children.

“I’ll give it some thought, but offhand I can’t come up with anyone who might be helpful with this.” He sighs and shakes his head. He seems truly sorry.

If I were to ask Al Capone to do me a favor, what kind of precedent would that be setting?

Chapter 38 What Happened?

She’s always crabby and everything she eats is boiled. Boiled cabbage. Boiled turnips. She even boils hamburger.

Chapter 39 The Warden

“Natalie!” I wrap my arms around her in a spontaneous bear hug.

My dad nods. “Apparently he’s been planning this for some time—been waiting for the right moment to launch it.”

Chapter 40 Al Capone Does My Shirts

Inside is one word scribbled hastily in pencil and underlined twice.