The Whipping Boy

The Whipping Boy is a middle grade historical novel written by American author Sid Fleischman and published in 1986. The novel won the Newbery Medal (awarded by the American Library Association) in 1987. When it was published, Fleischman had already written many books for both young and adult readers, often incorporating his interest in history, and setting books in different locales and time periods. In 1994, the novel was adapted into a film called Prince Brat and The Whipping Boy; Fleischman wrote the screenplay for the adaptation. The novel explores themes of friendship, social class, and growing up by portraying a young prince and his servant running away and embarking on adventures.

This guide is based on the 1986 Greenwillow Books edition.

Content Warning: The Whipping Boy includes physical punishment of children and uses outdated terminology for Romani people. There is also a mention of animal betting and fights.

Plot Summary

Prince Horace, also known as Prince Brat, lives a life of luxury in a castle, but is selfish, spoiled, and arrogant. His tutors are often angry with him, but since they are not permitted to punish the prince directly, a young servant is hired to serve as the prince’s whipping boy. Whenever the prince does something bad, the whipping boy is beaten or whipped on his behalf. Jemmy is the prince’s whipping boy, who grew up in poverty. Jemmy resents his job and often wants to leave; however, he takes advantage of his position by learning from the tutors who vainly attempt to teach the prince.

One night, the prince decides to run away and forces Jemmy to come with him. The two boys don’t get far before they are accosted by two criminals named Billy and Cutwater. The criminals realize that one of the boys must be the prince, but Jemmy is able to trick them into believing he is the prince and that the true prince is a servant. Billy and Cutwater attempt to blackmail the king into giving them money in exchange for the safe return of his son; while this plot is unfolding, Jemmy and the prince manage to escape.

Jemmy and the prince encounter a man named Captain Nips, who helps them by transporting them in his wagon. However, Billy and Cutwater catch up to them and beat the young prince (whom they still believe is a servant). Billy and Cutwater are scared off by a young girl named Betsey and her tame bear, allowing Jemmy and the prince to escape once more. Jemmy, Prince Horace, and Betsey reunite with Captain Nips and accompany him to the fairgrounds on the outskirts of the city.

Surrounded by the common people of his kingdom (none of whom recognize him), the prince is surprised and saddened to learn that he has a bad reputation, and that people dread the day he becomes king. Jemmy and the prince also learn that Jemmy is being blamed for the prince’s disappearance, and that there is a reward for anyone who captures him. Jemmy panics that he is going to be recognized and captured, and he flees to the sewers. The prince follows him.

As Jemmy and the prince approach the entrance to the sewers, they run into Billy and Cutwater again. The two boys flee into the dark, rat-infested sewers, pursued by the criminals. With Jemmy’s expert knowledge of the tunnels, and some help from a rat-catcher, the boys are able to lure the criminals into a tunnel known to be infested with the largest, most vicious rats.

After exiting the tunnels, Jemmy and the prince bring Betsey and Captain Nips back to the castle so they can collect the reward for finding Jemmy. However, the prince intercedes and explains to his father that Jemmy saved his life and protected him many times. The king allows Jemmy to stay in the castle without any punishment and seems sympathetic to why the boys ran off. The prince promises to change his bad behavior. The novel ends happily, and notes that Billy and Cutwater stowed away on a convict ship, accidentally ending up on a prison colony island.