Is Machiavelli a teacher of tyrants, as so many today like to think? Or is he a benefactor of humanity, responsible for the freedoms that we have come to associate with the modern world? What if the answer to both questions is "yes"? To address these questions, we will engage Machiavelli's enormously influential Discourses on Titus Livius, a study that will shed light on his deeply complex presentation of princely politics and classical republicanism.