This paper explores possible important relationships and sympathies between Amartya Sen's Capabilities Approach framework for understanding the human condition and the educational ideas of John Dewey and Paolo Freire. All three focus on the importance of democratic values in a fair, well-functioning society, while Sen and Freire especially explore the difficulties and possibilities of oppressed populations. Sen suggests that all humans have a right to choice in determining their life trajectories and should be provided with the tools that allow them to flourish. Both education and democratic values play important roles in creating the types of context that allow individuals and communities to recognize a wide array of human capabilities. We suggest here that the theories of Dewey and Freire offer avenues through educational processes for developing these contexts for expanded human capability. Dewey suggests an educational approach that stresses democratic values and the ability and willingness of individuals to reach out towards new possibilities. Freire stresses the idea of praxis playing a central role in education--a focus on the cycle of everyday action, reflection, and re-creation of action that leads to productive changes in life trajectories. We argue that Sen, Dewey, and Freire together help to offer a new way of understanding education in the twenty-first century.