This article considers the possibilities of critical democratic education through the lived experiences of students at an urban U.S. public school. I show how students shape their own educational trajectories amid larger meta-narratives about schooling to illuminate the complexities and paradoxes of democratic schools. I argue that democratic schools are neither sites of transformation nor sites of despair, but rather sites where agency is negotiated, contested, and remade, often in unexpected, unassuming, and contradictory ways.