In this article, John Holst presents findings of his historical research on Paulo Freire's educational work in Chile from 1964 to 1969. Freire's "Education as the Practice of Freedom", which was written in 1965 from notes he brought from Brazil, was informed by a liberal developmentalist outlook. In contrast, his "Pedagogy of the Oppressed", written toward the end of his stay in Chile from 1967 to 1968, was influenced by Marxist humanist ideology. Considering this relatively rapid change in Freire's educational philosophy, Holst explores the manner in which Freire's time and work in Chile affected his ideological evolution. Holst contributes to Freirean studies by demonstrating that Freire's work in the Chilean political context proved to be decisive in his ideological and pedagogical growth. Freire's ideological evolution inspired his writing of "Pedagogy of the Oppressed", widely considered one of the most important books on education in the twentieth century. Ultimately, Holst argues that Freire's pedagogy, like all pedagogy, can only be understood fully when seen within the specific sociopolitical and economic contexts within which it developed. Pedagogies are collective in nature, and Freire's, as he himself recognized, was no exception. (Contains 9 notes.)