Everyone knows what 'Machiavellian' means, but what does Machiavelli really say? Reading his classical political texts, 'The Prince,' the 'Discourses on Livy,' and 'The Art of War' in the company of his literary works, including 'Mandragola,' we will examine how Machiavelli's ideas about power, deception, language, ethics, and representation emerged from his reading of Plato, Livy, Ovid, and Dante, while also exploring the reception and consequences of his ideas. Just as Machiavelli searched history for answers to his own political situation, our guiding question cannot help but be 'What would Machiavelli do?'