This collection of essays explores the ways in which the defense of liberty can be bolstered by use of a dialectical method—that is, a mode of analysis devoted to grasping the full context of philosophical, cultural, and social factors requisite to the sustenance of human freedom. Its strength lies in the variety of disciplines and perspectives represented by contributors who apply explicitly dialectical tools to a classical liberal / libertarian analysis of social and cultural issues. In its conjoining of a dialectical method, typically associated with the socialist left, to a defense of individual liberty, typically associated with the libertarian right, this anthology challenges contemporary attitudes on both ends of the political spectrum. Though this conjunction of dialectics and liberty has been explored before in several works, including a trilogy of books written by one of our coeditors (Chris Matthew Sciabarra), this volume will be the first one of its kind to bring together accomplished scholars in political science, economics, philosophy, aesthetics, psychology, law, history, education, and rhetoric.