Freedom’s Progress examines how political thought developed from the material and social foundations of early communities through the transformations of ancient, medieval, and early modern Europe. The course connects agriculture, urbanization, hierarchy, and state formation to Greek debates over nature, convention, justice, citizenship, slavery, and the purposes of political life. It follows these questions through Plato, Aristotle, Hellenistic philosophy, Cicero, Roman law, and Christian interpretations of authority. Augustine’s account of fallen humanity is contrasted with medieval traditions of natural law, customary restraint, reciprocal kingship, representation, and the common good. The course then explores universities, commerce, scholastic economics, church–state conflict, popular legislation, sovereignty, Reformation resistance, and Machiavellian statecraft. Throughout, it compares rival explanations of legitimate rule, coercion, property, equality, obedience, and liberty while showing how inherited ideas were adapted to changing institutions and conflicts.