Machiavelli is one of history’s most famous (or infamous) writers on morality. The Catholic Church banned his work, accusing him of undermining virtue itself. Philosophers have blamed him for the modern world’s declining sense of morality. To be called “Machiavellian” is rarely a compliment today. Yet others have long defended Machiavelli as a Renaissance man who sought to explain how the world really works. In this seminar, we will read some of Machiavelli’s writings, asking whether he was a moral monster, or whether his moral vision is actually closer to traditional Judaism than we usually think, and perhaps a corrective to some of the errors and illusions of the Middle Ages.