Through a comparison of Leo Strauss's and Raymond Aron's interpretations of Thucydides's history, this paper sheds light on the relationship between political history and political philosophy. In continuing the dialogue between the two thinkers, I demonstrate that in spite of their opposed views on modern historical consciousness, they converge in a defense of the object and method of classical political history. However, there is a deeper disagreement regarding the relationship between philosophy and politics. While Strauss makes the case for the compatibility of classical political history and classical political philosophy on the grounds that Thucydides is a “philosophic historian,” Aron argues that it is precisely because Thucydides is not a philosopher that he succeeds in understanding an essential feature of political things, namely, contingency in history.