Jemmy dreams of leaving the castle and returning to his previous life in the streets. What he does not expect, however, is for Prince Brat to show up in his room one night, insisting that Jemmy accompany him in running away. This sounds like a terrible idea to Jemmy, but when the prince gives an order, what is he supposed to do but obey? The unlikely pair quickly run into a whole host of complications -- greedy criminals, a bear, and royal soldiers among them -- leading to a final set piece in the sewers deep beneath the city.
All of this happens at an almost absurdly breakneck pace. The Whipping Boy is, at least in the edition that I read, a mere 90 pages. The plot is constantly in motion, with essentially no downtime. Kids who like a lot of action in their stories may find a lot to like here.
The book does strike me as an unusual Newbery choice, however. I didn't find the characters particularly compelling or well-developed, the setting is off-the-shelf quasi-medieval, and the prose is serviceable, but not more than that. That's not to say that I can't understand why The Whipping Boy was popular; words that Kirkus Reviews used to positively describe it at the time included "rollicking" and "melodrama," and both of those seem fair to me. If that's what the reader is looking for, they'll find it in this story, executed both briskly and well. But I'm still unconvinced that The Whipping Boy has many markers of the kind of literary excellence that the Newbery is supposed to recognize.
Possibly, it just wasn't considered a strong year. The three Honor books were A Fine White Dust, by Cynthia Rylant; On My Honor, by Marion Dane Bauer; and Volcano: The Eruption and Healing of Mount St. Helens, by Patricia Lauber. I know some elementary school kids end up reading On My Honor, but I don't think any of those books are considered upper-tier entries in the kidlit canon. The most highly-regarded books of the year all seemed to come from authors outside the USA -- Brian Jacques (Redwall), Diana Wynne Jones (Howl's Moving Castle), Philip Pullman (The Shadow in the North).
Sid Fleischman was a man with a fascinating life -- he worked as a professional magician, served in World War II, wrote screenplays, and published adult novels, in addition to his work for children. Though he won the Boston Globe-Horn Book Award in 1979 for Humbug Mountain, The Whipping Boy represented his only appearance on the Newbery rolls. His son, Paul Fleischman, would win the Newbery two years later for Joyful Noise, making them the only parent-child combo to ever take home the gold medal.