Reading Through History: The Whipping Boy by Sid Fleischman (1986)

The Whipping Boy is a slim historical fiction novel that won the Newbery Medal back in 1987. It’s the story of Prince Horace, also called Prince Brat, who often misbehaves on purpose in order to see his whipping boy, Jemmy, get punished. When the prince runs away and Jemmy follows, they fall in with some criminals and must switch places in order to outsmart them and make their escape.

Of all the relationships presented in children’s books, this one, between a prince and the boy who is punished daily on his behalf, is one of the most unusual and the most interesting. Though the story is mainly an adventure, following the two boys as they try to outsmart a pair of ne’er-do-wells, it also raises a lot of important questions about wealth, status, education, and justice. The prince is rich and powerful, but he has never learned to read or write because he is always busy misbehaving. The whipping boy, however, who can afford to take nothing for granted, has learned the lessons intended for the prince and is fully literate. Inside the castle, the prince’s crown gives him authority; outside the castle walls, Jemmy becomes the powerful one because he can read and write. When the boys trade places, it’s not just a cute Parent Trap-esque plot device. Instead, the swap is used to illustrate the mostly arbitrary societal constructs that separate the haves from the have-nots. The reader learns, without explicitly being taught, that there are different types of riches, and that the last can suddenly be first when circumstances shift and change.

There are many other elements to this book that make it great. I’m sure kids are pleased to see Prince Brat get his comeuppance after Jemmy has endured so many beatings in his stead, but I bet they enjoy his journey toward redemption just as much. Each character the boys meet on their journey back to the castle is colorful and memorable, and the boys’ clever plan for finally escaping their captors makes for a very satisfying ending.

This book reminds me a lot of The Tale of Despereaux, and I think fans of one will equally enjoy the other. It’s also a nice, quick read with lots of action that a reluctant reader might be willing to try over something longer and more intimidating. I like Sid Fleischman’s straightforward writing style, and though I saw the happy ending coming from the beginning, the road he took to get there was thoroughly enjoyable.