Can one man be all of these and more? How did his name become synonymous with nefarious treachery and arguing that the end justifies the means? When did he become the face of political casuistry and Catholic deception? And all of this on the basis of a slim volume, called "The Prince", published about five hundred years ago, which few people have actually read. This course will examine this text and excerpts from Machiavelli's "Discourses" on Livy to address some of the questions raised, place them in their contemporary and into a modern context, and try to come to a nuanced understanding of Machiavelli's actual arguments and his significance to our thinking about politics, morality, and business. One might even argue that appreciating the power of this text is essential to an understanding of modern business and politics.