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Once a troublemaker, always a troublemaker? A reputation proves challenging to change in this “rock-solid school story” (Publishers Weekly) from Andrew Clements.

Clayton Hensley is accustomed to trouble: There’s a folder of incident reports in Principal Kelling’s office that’s as thick as a phonebook and growing daily. Most recently, Clay’s art teacher told the class to spend the period drawing anything they wanted, and Clay decided to be extra “creative” by drawing a spot-on portrait of Principal Kelling…as a donkey.

It’s a pretty funny joke, but Clay is coming to realize that the biggest joke of all may be on him. When his big brother, Mitchell, gets in some serious trouble, Clay decides to change his own mischief-making ways…but he can’t seem to shake his reputation as a troublemaker.

From the master of the school story comes a book about the fine line between good-humored mischief and dangerous behavior—and how everyday choices can close or open doors.

Product Details

ISBN-13: 9781416949329
Publisher: Atheneum Books for Young Readers
Publication date: 02/05/2013
Edition description: Reprint
Pages: 140
Sales rank: 142,389
Product dimensions: 5.32(w) x 7.52(h) x 0.48(d)
Lexile: 730L (what's this?)
Age Range: 8 - 12 Years

About the Author

Andrew Clements is the author of the enormously popular Frindle. More than 10 million copies of his books have been sold, and he has been nominated for a multitude of state awards, including two Christopher Awards and an Edgar Award. His popular works include About Average, Troublemaker, Extra Credit, Lost and Found, No Talking, Room One, Lunch Money, and more. He is also the author of the Benjamin Pratt & the Keepers of the School series. He lives with his wife in Maine and has four grown children. Visit him at

Keith Nobbs has appeared on Broadway in The Lion In Winter and off-Broadway in Dog Sees God, Romance, The Hasty Heart, Bye Bye Birdie, Dublin Carol, and Four (Lucille Lortel Award, Drama Desk Nomination). His film credits include Phone Booth, Double Whammy, and 25th Hour. Television credits include The Black Donnellys (series regular), Law and Order: Criminal Intent, and The Sopranos.

Read an Excerpt


  • Clay Hensley frowned at the paper on the table. It wasn’t a very good drawing. He’d made tons of better ones . . . like that picture he’d made of the old man sitting on the bridge? Now, that was good—even won a prize. This drawing? It was okay, just a simple portrait. It wasn’t going to win any prizes—but then, it wasn’t supposed to. It was supposed to do something else. Soon.

    Out of the corner of his eye Clay saw Mr. Dash get up from his desk. The class period was almost over, so the art teacher was beginning his inspections, same as always.

    Clay squinted and kept working on the portrait, shading a little here, erasing a little there, trying to get the expression on the face just right—actually, trying to get the whole head to look right. It wasn’t easy.

  • What People are Saying About This

    From the Publisher

    "Clements is a genius of gentle, high-concept tales set in suburban middle schools."—The New York Times

    "Another rock-solid school story that will resonate with middle graders."—Publishers Weekly

    Reading Group Guide

    A reading & activity guide for

    Troublemaker by Andrew Clements


    Clayton Hensley has been getting into trouble since he started elementary school. From running in the halls to drawing an unflattering cartoon of the principal, he’s always been pretty proud of his pranks. Then his big brother, Mitch, returns home from a stint in jail with a new attitude and wants Clay to change his ways too. But Clay’s rambunctious friends don’t understand. Resisting the urge to act up when somebody bugs him is not as easy as he thought it would be. And a few weeks of good behavior may not be enough for the people Clay tricked and ridiculed to stop thinking of him as a troublemaker. Clements tells a thought-provoking and important story about rules, reputations, and the possibility to change course for the better.


    1. List at least three things you think you know about Clay after reading only the first page of Troublemaker. What is your opinion of Clay at the end of Chapter 1?

    2. Who is Mrs. Ormin? How does she help readers understand Clay’s story? How does Clay feel about Mr. Dash, Mr. Kelling, and Mrs. Ormin? Is he angry at them? Why do you think Clay behaves the way he does in the early chapters of the book?

    3. What do you think Clay expected would happen after Mr. Dash and his classmates see the donkey picture? What events resulting from the inappropriate drawing surprise Clay?

    4. If you were the school principal, would you have dealt with Clay’s disrespectful cartoon in the same way as Mr. Kelling? What message would you have wanted to get across to Clay? Explain your answer.

    5. When we first meet Clay’s brother, Mitch, he has just been released from jail. Why was he there? How have Clay, his mom, his dad, and Mitch himself reacted to this experience?

    6. Is the Mitch who came home from jail the person Clay was expecting? How does Mitch respond when Clay shows him the donkey portrait?

    7. Why does Mitch want Clay to start behaving better? Why does he ask Clay to trust him? Why does Clay decide to do so? How do you decide whether or not to trust a person?

    8. List at least three things that Mitch makes Clay change about his appearance. Why might this help Clay make the more important change—to his attitude? Do the clothes and hairstyles of your classmates affect the way you think about them?

    9. On his first day at school with his new look, what opportunities for trouble does Clay resist? How does Clay’s friend Hank react to the new Clay? How do Clay’s other classmates and teachers react?

    10. Why does Clay have so many suspects to consider when he wonders who defaced his self-portrait? What does this say about Clay? Why does Clay stay home on Halloween night?

    11. How does his family react when the police come looking for Clay? Why is the trust Clay put in Mitch important now? How else does trust play a role at this moment in the story?

    12. What does Clay realize about his father’s attitude toward himself and his big brother? Is Clay surprised by his realization? Why or why not?

    13. Do you think Mr. Kelling was right to suspect Clay of painting his door? Would you have suspected Clay? Was Clay right to go to Mr. Kelling’s house the next day? How does Clay look back on past Halloweens now?

    14. Compare Clay’s drawing of the donkey-face principal to Hank’s destruction of Clay’s self-portrait. How are these actions similar? What do you think Clay comes to understand about each of them? Do you think Clay and Hank will remain friends? Explain your answer.

    15. How is the transcript of first-grader Clay’s visit to the principal’s office different from the transcript of his last sixth-grade visit? What do you think the future holds for Clay?


    1. Imagine you are another student in Mr. Dash’s art class, along with Clay. Write a two to three paragraph journal entry describing the day Clay drew the donkey-principal picture and how you felt about it. Consider noting how you imagine Mr. Kelling will feel when he sees the picture and/or what you think of Clay.

    2. In the character of Clay a week before the story begins, write a one-page letter to your brother Mitch in jail. How are you feeling? What do you want to do with Mitch when he returns home? What do you want him to know?

    3. Get a copy of your school’s student handbook or rules of conduct. Find out what type of punishment you think Clay would have received if he had been a student at your school when he drew the donkey cartoon. With friends or classmates, discuss what you feel would have been the most appropriate discipline for Clay.

    4. Cut pictures of kids and teenagers from old magazines and newspapers. Holding up one picture at a time, ask classmates to describe the kind of students or friends they imagine each person would be, based on their clothing and hairstyles. Discuss your results. Do most people make the same decisions about the pictures they see? What clothes, hairstyles, colors, or accessories tend to cause people to make assumptions about an individual? Is it right to make these assumptions? Write a dress code for your school based on this discussion.

    5. When Clay changes his behavior, his goals change too. He begins to take drawing more seriously. On a sheet of paper, write down your goal or goals for the school year. Goals can be related to schoolwork, sports, other activities, your family, or your community. Below your goal(s), write down what attitudes and actions might help you achieve these goals. If desired, discuss your goals with a parent, teacher, or other adult who might have some suggestions to help you reach them.

    6. With a friend or classmate, role-play a conversation between Clay and Hank in which the truth about the defaced self-portrait is revealed, or a conversation between Clay’s mother and father in which they discuss whether or not to believe Clay is innocent of the Halloween graffiti incident. Then, discuss with friends or classmates whether you think there is a “right” and a “wrong” person in either one of these scenarios.

    7. Clay is a talented artist who, at the end of the story, discovers that drawing can be even more rewarding than pulling pranks. Go to the library or online to find careers that would be good for someone with Clay’s talents, such as animator and graphic designer. Make a list of at least ten jobs to recommend to Clay.

    8. In the character of Clay, write a paragraph describing how and why you decided to include the donkey mask in your prize-winning self-portrait.

    9. Use colored pencils to make your own self-portrait. Include your face as well as at least one other object or image that shows something special about your goals or your attitude.

    Customer Reviews

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    Troublemaker 4.2 out of 5 based on 0 ratings. 52 reviews.
    Anonymous More than 1 year ago
    Funny book laughed my head of!!!!!
    Anonymous More than 1 year ago
    This book is so cool It is so suspenful Very cool A must have
    Anonymous More than 1 year ago
    This book is perfect for young readers to read.
    Anonymous More than 1 year ago
    Grear book. All andrew clements books are.
    Anonymous More than 1 year ago
    LOOKS FUN!!!
    Anonymous More than 1 year ago
    Everybody makes mistakes and now Clay is starting to relise that.....i really like this book.....i really like andrew clemets he is my favorit author!!!!! :)
    Anonymous More than 1 year ago
    I loved this book do much! I really reccomend it.
    Anonymous More than 1 year ago
    I LOVE THIS BOOK ITS THE BEST BOOK EVER!!!!!!!!!!!!!!!!!!,
    Booklady123 on LibraryThing More than 1 year ago
    From the inside flap:¿Once a troublemaker, always a troublemaker?There¿s a folder in Principal Kelling¿s office that¿s as thick as a phone book, and it¿s growing daily. It¿s filled with the incident reports for every time Clayton Hensley broke the rules. There¿s the minor stuff, like running in the hallways and not being where he was supposed to be when he was supposed to be there. But then there are also reports, like the most recent addition, that show Clay¿s own brand of troublemaking: The art teacher had said tha the class should spend the period drawing anything they wanted, and Clay decided to be extra ¿creative¿ by drawing a spot-on portrait of Principal Kelling . . . as a donkey.It¿s a pretty funny joke, but Clay is coming to realize that the biggest joke all may be on him. When his big brother, Mitchell, gets in some serious trouble, Clay decides to change his own mischief-making ways . . . but he can¿t seem to shake his reputation as a troublemaker.¿Clay is one of those students ¿who is not living up to his potential.¿ He idolizes his older brother and wants to follow in his mischievous footsteps. At first I worried that this book might be a ¿bad influence¿ by giving kids ideas for making trouble (and it does, but nothing a mischievous child hasn¿t already thought of). But it also sets a good, if someone simplistic example. Clay¿s admiration for his older brother Mitch may get him into to trouble in the beginning, but it also puts him on the right path to making better choices.What I liked about the book: It provides a good message in simple and humorous terms. The writing is typical Clements and will appeal to students and educators alike. Mark Elliott¿s illustrations have a feel as though they were done by a talented student, which will have great appeal for readers.What I don¿t like about the story: The message is a little oversimplified. Though I think the simplicity of the story makes it perfect for its targeted audience it might also give the impression that changing one¿s behavior can happen virtually overnight. It has the feel of an ¿after school special¿ where everything is solved in a couple of hours.Overall this is a good read and I recommend it for Clements fans and anyone who wants to impart a message about how your choices tend to follow you.Recommended for 3rd grade and up.Mrs. Archer¿s rating: 4 of 5
    abbylibrarian on LibraryThing More than 1 year ago
    Clay is a troublemaker. He doesn't pull pranks to be mean or because he's angry, but because his older brother was a prankster and Clay's following in his footsteps. In fact, when Clay uses his time in art class to create a hilarious picture of the school's principal as a jackass, he can't wait to show Mitch and tell him the story of what happened. But Mitch is, for the first time, unimpressed by Clay's prank. Just home from a 30-day jail sentence, Mitch knows it's time for him and Clay to turn their acts around. Mitch makes Clay promise not to pull any more pranks and to start working harder in school. But when someone vandalizes the principal's house on Halloween, all fingers point to Clay. Can he prove his innocence? While I like the subject of this book, it's not one of my favorites of Clements'. The whole story is slight and quick and wraps up way too easily. Clay barely has any trouble switching gears and I found the pat ending a bit hard to buy. This might make an excellent choice for certain spirited children who might be heading down a bad path (or driving you crazy). Its slim page count will up the appeal for reluctant or high-low readers, but otherwise I'd skip it and pick up Frindle, No Talking, The School Story, or The Last Holiday Concert (my favorites).
    erineell on LibraryThing More than 1 year ago
    Clayton Hensley is in 6th grade. He has more referrals and visits to Principal Kelling's office than anyone else in the history of the school aside from his older brother, Mitchell. Clay finds pride in his behavior and is excited to share with his brother his latest disruptive deeds- drawing a portrait of his principal, as a jackass, in art class. But, when Mitchell returns home from jail changed, it makes Clay reconsider his actions. This story, Troublemaker, tells in third person Clay's struggles of making good choices and the consequences of having a reputation of being a troublemaker. Author Andrew Clements writing style flows easily and honestly portrays the realities of life in middle school for some children. This story will peak and keep the interest of many readers and cause one to reflect on their own actions. Readers need to be aware that the word "jackass" is used derogatorily.Age Appropriate: 5th to 8th grade
    ALelliott on LibraryThing More than 1 year ago
    Meet Clay, who absolutely idolizes his older brother, Mitch. Everything Clay does, from drawing a funny-mean picture of the principal to ducking his office disciplinary meetings, he has only one thought in his head, "Man, I can't wait to laugh about this with Mitch." But he'll have to wait a little longer, because Mitch is in jail. And when Mitch gets home, he has some ideas about how Clay should live his life from now on. But no matter what Clay does, he can't seem to escape his bad reputation (cue electric guitars).I'm not familiar with Andrew Clements, but apparently he wrote a bestseller called Frindle. Based on this book, I'm willing to check that one out. The age group of the kids in this story is sixth grade, making it perfect for 7th graders who might miss sixth grade life, or fifth graders looking ahead. While the book packs a pretty powerful message about the joys of staying out of trouble, kids with real disciplinary issues might find it a little hokey. But if you've got a sweet goofball, this might be the book for them. For middle schoolers, the print is pretty large, and some of your kids might dismiss it as childish as a result, and I hate to say it, but the cover is really unattractive. Still, that's why we don't judge books by their covers, right? (I totally do...)Anyways, good book for struggling readers, kids who are silly, or kids looking for a fast-paced read who don't really dig the fantasy thing. Decent writing, relatable characters, and a believable plot add up to a nice little read for middle schoolers. The only part I had trouble with is when the characters, as 5th graders, snuck out of the house at 1:00 am to smash pumpkins on Halloween. But then, I am, and always have been, a serious goody-goody.For 5th - 8th graders
    Anonymous More than 1 year ago
    I love all Andrew Clements books
    Anonymous More than 1 year ago
    Very good.
    Anonymous More than 1 year ago
    I love all of andrew clements books
    Anonymous More than 1 year ago
    The best book ever!!!
    Anonymous More than 1 year ago
    It was a really good book and i love andrew clements i hope you will enjoy it!!
    Anonymous More than 1 year ago
    Anonymous More than 1 year ago
    This book is amazing!!!!!!!! I lovd it so much
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    Anonymous More than 1 year ago
    i love it when he draws the pictur of the principal as a donkey!!!!!!
    Anonymous More than 1 year ago