In this chapter I explore three influential themes of contemporary Jewish education, personal autonomy, positive law, and national sovereignty, from a postmodern perspective suspicious of hidden power relations. After situating these themes along with postmodern discourse in the dynamics of Enlightenment thought, I consider how analytic methods advanced by Michel Foucault, Jacques Derrida, and Jean-Francois Lyotard reveal ways in which contemporary liberal, Orthodox, and Zionist Jewish education seek to dominate others. This is followed by an examination of three paradoxes inherent in the postmodern preoccupation with power and a discussion of how Jewish education might avoid them by engaging the post-Enlightenment thinking of Emmanuel Levinas, Michael Oakeshott, and Isaiah Berlin.