Critical pedagogues advocate a constructivist approach to learning emphasising the self-directed construction of knowledge from the learners' experiences while also expecting students to develop an explicit critique of the social order. 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 the anti-oppressive conclusions teachers desire? Using comparative historical archival methods and oral history interviews, this study interrogates how teachers and students navigated this paradox in the Berkeley Experimental Schools Project (1968-1975), a public educational programme that sought to actualise the goals of both the Free School and Black Power movements. This study sheds light on this dilemma with particular clarity because the Free Schools represent one of the U.S.' most radical experiments in constructivist pedagogy, and the Black Power movement one of our most heightened efforts to challenge systemic oppression. In demonstrating that in Berkeley, it was easier to build self-directed inquiry on a foundation of explicit critique than to build anti-racism on a foundation of free inquiry, this study elucidates tensions at the heart of critical pedagogy, social justice education, and curriculum theory.