Rupert is extremely poor. His family lives on oatmeal and kitchen scraps. He sleeps under the bed and wears all three of his shirts in winter. So it is really surprising when he finds himself at the richest house in town on Christmas. The Rivers family is very rich and very eccentric. They play games for their Christmas presents in a cut-throat fashion. Rupert is ecstatic when he whens all the presents; he is especially excited about the new pair of boots since his sneakers are wearing out. But then he loses it all in the final game and is sent home empty handed. 

The rest of the the story consists of episodes where different members of the Rivers family take Rupert on adventures. Somehow he never gets enough to eat on any of these though. The Rivers are sort of well-meaning, but ultimately selfish and self-centered, never really thinking of Rupert. The story ends with Rupert realizing that being rich doesn't make you happy or satisfied with your life. However, his circumstances never change. He is just as poor and hungry at the end of the book as he was at the beginning. 

I didn't get the point of it at all. It was an interesting and entertaining story, but I was put off by the thoughtlessness of the Rivers family. Not a single one of them truly helped Rupert or his family in any way. Definitely not my favorite book.