Niccolò Machiavelli died nearly 500 years ago, but his name lives on as a byword for cunning, duplicity, and the exercise of bad faith in political affairs. So much notoriety has gathered around Machiavelli’s name that the charge of being a machiavellian still remains a serious accusation in political debate. What lies behind the sinister reputation Machiavelli has acquired? Is it really deserved? What views about politics and political morality does he put forward in his major works? In order to understand Machiavelli’s doctrines, we need to begin by recovering the problems he evidently saw himself confronting in The Prince, the Discourses, and his other works of political thought.