Piero Chiara was one of the most important and prolific writers of the Italian twentieth century. In this scientific contribution, some aspects of his literary production are analyzed with specific reference to the works dedicated to children. In particular, the article focuses on a well-known character, namely Pierino. The child, with a lively and naughty character, is a troublemaker, and in him we can trace some autobiographical elements relating to the writer’s childhood, lived entirely in Luino, a small Lombard town.