John Dewey's pragmatism and progressive education sought to nourish the democratic principles of critical thinking and collective social action, which he saw as central to democracy and threatened by what Jürgen Habermas would call the rise of "instrumental rationality." Dewey was concerned that traditional approaches to education operated to limit student growth and failed to nurture the skills and knowledge they needed to address contemporary experiences, issues, and problems. Recognizing students as active participants in the construction of knowledge and the decisions that affect them, Dewey had a radical democratic vision that centralized the role of education in its creation. There is much to gain from his revolutionary educational philosophy and the direct link he saw between education and personal and social transformation. At the same time, however, one needs to recognize that his neglect to deal with the issues of racial segregation and the status of blacks as second-class citizens, precluded the possibility of realizing his vision. In this essay, the author argues that Mississippi freedom schools can be understood as an important critical intervention to such antidemocratic oversight from which there is much to learn. She looks particularly at the conceptions of pedagogy, citizenship, and power as operationalized in the formation of freedom school curriculum. In so doing, she offers a sketch of how the most revolutionary of twentieth-century educational theories provides fruitful strategies for fostering the capacities of critical thinking, imagination, and collective action but need to be further developed, as each, in some way, wound up reinforcing aspects of the very undemocratic principles that they deplored and struggled against.