There is much in Freire's educational philosophy that can be helpful in the reading of a fictional work; similarly, in engaging fiction, the understanding of key Freirean principles can be deepened. These dual possibilities become evident in reflecting on his countryman Lima Barreto's novel, "The Sad End of Policarpo Quaresma" (Barreto, 2011). Barreto's work has received comparatively little attention in the English-speaking world. Even in his own country, Barreto was, for many decades after his death, treated as a marginal figure in Brazilian literature (Aidoo & Silva, 2013, p. 1). Today, however, he is regarded as "one of Brazil's most published and debated authors" and "The Sad End of Policarpo Quaresma" is considered to be "his most important work" (Serra, 2011, pp. 28, 37). The novel is both a searching examination of a country undergoing political change and a nuanced study of human fragilities. This article focuses principally on the second of these two dimensions, and considers Barreto's central character from a Freirean perspective. The author argues that while Freirean theory allows the adoption of a compassionate stance in seeking to understand Policarpo Quaresma, the ethical and pedagogical questions raised by his "madness" find no easy answers. The author concludes that Barreto has something significant to teach about the complexities of humanization and the limits of critical education.