Because of the public identification of both Michael Oakeshott and Leo Strauss as conservative political philosophers, there have been numerous comparisons of their political thought. Whatever similarities or differences that do exist between them, it is certainly true that they shared a keen interest in the history of political thought. However, they understood the character of history in widely divergent ways. In the following paper, I examine the way in which each writer understood the logic of historical explanation, and there are two primary reasons for wanting to do so. First, there have been few examinations of either writer’s arguments concerning historical understanding, despite the stature of both as historians of political theory. Second, the differences between Oakeshott and Strauss on history are central to two fundamentally opposed ways of understanding the past, each of which has manifested itself in the contemporary practice of the history of political thought. I will argue that Strauss’s approach to the past is primarily a practical one and yields a concern with a legendary or mythical past constructed primarily to address contemporary political problems, and that his specific methodological propositions are either irrelevant to a specifically historical understanding of the past or inadequately argued and unconvincing. Conversely, I will suggest that Oakeshott offers a coherent and compelling account of the logic of historical understanding, which involves both a defense of the autonomy of historical explanation and an elaboration of the character of historical contextualism.