This study examines two contradicting priorities that have always stood at the heart of liberal democratic pedagogy and continue to be prominent in “social justice” education and critical pedagogy today. The first is the task of cultivating students’ commitment to democratic values and challenging oppression, and the second is the task of fostering the capacity of the individual for autonomous critical thinking. Both are expressed within critical pedagogy. Critical pedagogues advocate a constructivist approach to learning - which emphasizes the autonomous, self-directed construction of knowledge from the learners’ experience - while at the same time expecting students to develop an explicit critique of the social order (Freire, 1970). However, the use of a constructivist approach for the pursuit of explicit ideological goals leaves educators with a dilemma: what happens when students’ reflections don’t lead them to conclusions that challenge oppression? Using historical archival methods and oral history interviews, my research interrogates how teachers and students navigated this contradiction in the Berkeley Experimental Schools Project (1968-1975), a public educational program that sought to actualize the goals of both the Free School and Black Power movements.