Paul Cantor’s study of Shakespeare centered on the three Roman plays, Coriolanus, Julius Caesar, and Anthony and Cleopatra. In his two books, Shakespeare’s Rome and Shakespeare’s Roman Trilogy, Cantor argued that Shakespeare uses the plays to develop an interpretation of Roman history from the height of the Republic through its fall, culminating in the Roman Empire. Shakespeare, on Cantor’s telling, displays a shrewd understanding of the strengths and weaknesses of the different regimes and the human character each regime was dependent on and tried to develop. Not content with portraying Shakespeare as a political philosopher, Cantor argued that he also presents an interpretation of the rise of Christianity that bears a striking affinity with Nietzsche’s view of this topic, and comparisons with Hegel are made as well. In this essay, I concentrate on the interpretation of Christianity and its conflict with the Empire, though with some attention to the theory of government during the Republic as well. Cantor wrote from a perspective much influenced by Leo Strauss, and I will assess the merits and difficulties of this approach.