In the deepest sense, this Article seeks to bridge the gap between philosophy, political theory, and constitutional law. It examines how our constitutional tradition conceives of freedom, perhaps the most important value in the American legal order. It discusses five distinct though intertwined traditions, each drawn from a different philosophical theory of freedom. These five faces of freedom are (1) the "positive" ideal—freedom as the right to vote and to take part in government, (2) the "negative" ideal—freedom from constraint or government interference, (3) the progressive ideal, (4) self-individuating liberalism— freedom as the right to discover, develop, and express one's core identity, and (5) the "homeostatic-communitarian" ideal—freedom as inhering in a network of communal social relations located within a broader pluralistic society. Each Part. provides an overview of the philosophical foundation of one of the faces of freedom and then traces its constitutional development. The Article concludes by discussing how the contours of freedom have changed over the course of our history.