As the Roman Republic died, freedom was in a state of conceptual chaos. Cicero and Horace, in successive generations, responded to this intellectual and spiritual crisis with a comprehensive rethinking of freedom. Cicero returns to basics: the human being, at once constrained and free. By founding freedom (libertas) on his view of the human being (humanitas), Cicero develops a consistent theory of freedom across the domains of politics, ethics, and the liberal arts. Horace inherits this project after the Republic is gone. His challenge is to explain what freedom can mean in a situation of permanent constraint, and he too starts with the human being as constrained and free. Scholarship on libertas has tended to focus on conceptual passages about political freedom. I expand the corpus of relevant texts by considering the extensive figurative language of binding and release, and by giving equal attention to political and moral freedom, the liberal arts, and aesthetic freedom.