After the fall of communism in Europe, it was thought that those in the East would look westward to learn about building stable, vibrant democracies. This dissertation, however, proceeds against the current, and considers what the East can teach the West (and the world in general) about the as-of-yet-unexplored possibilities latent within democratic politics. While focusing on the role of the post- and non-Marxist Left in Eastern Europe, my research explains how radical, emancipatory thought and engagement took a non-violent, democratic turn, and subsequently aided in the development of what later came to be known as civil society. Thus, my dissertation offers an answer to the following question: What can the Left's role in the revival of engaged citizenship and democratic politics in Eastern Europe teach us about confronting the enduring dilemmas associated with making democracy work? The analysis critically assesses the East European dissident experience, between the crushing of Czechoslovakia's Prague Spring (1968) and the East European revolutions of 1989. It finds that democracy was able to develop in this hostile environment because the opposition remained committed to a non-violent, pluralist spirit of radical political theory and praxis. Furthermore, by revisiting the emergence of democracy precisely where it was not permitted to exist, this research re-presents the East European dissident experience as a constellation of ideas and actions that challenges us to reconsider contemporary forms of citizenship, political engagement, and democracy.