By placing John Dewey between John Rawls and Richard Bernstein, I argue for a socialist reading of Dewey’s takes on liberal democracy that moves away both from conservative readings of Dewey of those who claim that his democratic liberalism actually belongs to right-wing or center views, and from left-wing, communitarians who dismiss such views as irrelevant for socialist and radical variants of liberal democracy. Overall, it can be shown that Rawls and Dewey’s different takes on political liberalism could be ultimately reconciled, given their similar takes on democracy, pluralism, and the person. Rawls’ rehabilitation of Kant can itself be shown to be closely related to his reading of Dewey. Furthermore, as Bernstein argues, such a renewal of Dewey’s social and political philosophy in Rawls’s political constructivism and reflective equilibrium was decisive for the great pragmatist turn observed in the second, third, and fourth generations of critical theory, not only in the so-called Frankfurt School (especially Habermas, Honneth, Forst) but also in feminist and decolonial thinkers such as Nancy Fraser, Seyla Benhabib, Judith Butler, Rahel Jaeggi, and Amy Allen. Dewey’s pragmatist turn in political philosophy allows thus for a dynamic, robust correlation between radical democracy and public education, which could be implemented in emerging democracies like Brazil.