[The Whipping Boy]: A Review

Hi y’all!

Today I am excited to share my review of The Whipping Boy by Sid Fleischman, winner of the 1987 Newbery Medal. As I’ve mentioned in a few recent posts, I am terribly behind on reviews right now. So I’m trying to post a few a week to catch up! It’s a good place to be though–lots of great reading the past few months!

I again have to give credit to my mom for introducing this book to me. It was one of her recently read favorite Newbery winners. And now it’s one of my new favorite winners as well! I loved this Newbery Winner that was a short, engaging read.

Initial Thoughts:

  • Fun fact: Sid Feischman ‘s son Paul Fleischman also won the Newbery Medal for his Joyful Noise: Poems for Two Voices collection of insect inspired poetry. Even more interesting is that they won only two years apart–1987 and 1989. How cool is that father and son are both Newbery winners!?
  • This is another quick, engaging Newbery winner. I read this one in about an hour. The story is fast paced with the boys on their adventure by page 10. The illustrations were a fun touch as well to give life to the characters in a different way. I am enjoying this shorter Newbery winners!


According to Goodreads, “A shout comes echoing up the stairway. “Fetch the whipping boy!” A young orphan named Jemmy rouses from his sleep. “Ain’t I already been whipped twice today? Gaw! What’s the prince done now?” It was forbidden to spank, thrash, or whack the heir to the throne. Jemmy had been plucked from the streets to serve as whipping boy to the arrogant and spiteful Prince Brat.

Dreaming of running away, Jemmy finds himself trapped in Prince Brat’s own dream at once brash and perilous.

In this briskly told tale of high adventure, taut with suspense and rich with colorful characters, the whipping boy and Prince Brat must at last confront each other. Award-winning author Sid Fleischman again blends the broadly comic with the deeply compassionate in this memorable novel

I loved Jemmy’s (the whipping boy) character as it gives a history to someone who was probably often overlooked in the castle. He is easy to cheer for and is seriously clever! I hadn’t heard of whipping boys before this novel and their role in the castle is fascinating and surprising. No wonder Prince Brat never behaves when someone else takes his punishment for him! I enjoyed Jemmy’s courage and his street wisdom. And I was surprised right along side him when he discovered that he actually wanted to help the Prince and felt he would fit in at the palace after all.

Prince Brat is a character you love to hate and then find yourself cheering for. He is ridiculous at the beginning of the story! From forcing Jemmy to run away with him to literally bringing his crown and half a banquet with him, I couldn’t believe how arrogant and mean this kid was. No wonder everyone called him Prince Brat. But the most intriguing part of this story is the Prince’s changing mindset. The moment he and Jemmy are mistaken for each other and he receives a beating on Jemmy’s behalf is one of the most starkly illuminating moments of the story. In fact, I would say it is the most fascinating scenes in the book. And I think that’s the turning point in the story as well. That’s when his character and the whipping boy’s starts to change. And it just goes to show that even spoiled Prince Brat can learn his lesson.

This is a classic adventure story. Jemmy and Prince Brat both want to run away because they want freedom from what they believe to be unbearable roles in the castle. Almost instantly, they are captured by thugs that want ransom from the king and are also dumb enough for Jemmy to fool. When they escape once, the thugs continue to chase them all over the kingdom. Along the way, our unlikely heroes meet new friends. I particularly enjoyed the performing bear and the potato seller the duo meet. And like all classic adventure stories, we have an exciting climax and a satisfying ending. Although, I must admit I cringed when they were in the sewer and the rats attacked. So glad I didn’t live as a commoner back then! This story will keep you on the edge of your seat for the whole ride!

Fascinating history!! I love that this is based on real whipping boys and love the mythic feel of the story. A well deserved winner!

green stargreen stargreen stargreen stargreen star

Have you read any other books set in the medieval era?
Which were your favorites?


I read this Newbery Medal winner as a part of my Newbery Challenge.
I plan to read all 100 Newbery Medal winners by the end of 2022, the year the 100th winner is announced.

5 thoughts on “[The Whipping Boy]: A Review

  1. Pingback: 7 Books to read with Unique Historical Settings – greenish bookshelf

  2. lydiaschoch

    I read this story when I was a kid! I no longer remember how it ended (or what much of the plot was), but I believe I liked it quite a bit.

    Thanks for that blast from the past. 🙂

    Liked by 1 person

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