This article addresses the disturbing fact that few contemporary Chilean children's books deal with Augusto Pinochet's dictatorship (1973-1990). It explores why dictatorship has such an elusive presence in contemporary Chilean children's literature, how it has been represented in general, and how children are portrayed in books that do address Pinochet's oppressive regime. Four Chilean children's books are examined in detail: two that represent the dictatorship from an outsider perspective, produced by authors in exile, and two written from an insider perspective by authors that grew up under Pinochet's dictatorship. While the former represent children as superheroes whose actions transcend the dictatorship's repression, the latter depict children who are politically aware, but do not make the adults' political fight their own. This key difference is problematized in terms of the implications for narratives of dictatorship produced for a young audience.