Michael Oakeshott’s distinction between the practical and the historical past has been the focus of much discussion in contemporary theory of history. This is primarily due to Hayden White’s appeal to Oakeshott’s distinction in several recent works. However, the philosophical underpinnings of Oakeshott’s distinction are seldom discussed. This essay provides a philosophical elaboration and critique of both Oakeshott’s distinction and White’s use of it. Oakeshott’s distinction is expounded as an integral part of his idealist philosophy. My contention is that in order to properly understand the distinction, we must first understand Oakeshott’s theories about different modes of understanding to which different kinds of past belong. Besides comparing White and Oakeshott, this essay will also develop a critique of the distinction between history and practice. The main claim of the essay is that there are important internal connections between history and practice that Oakeshott’s distinction neglects. In conclusion, I argue that the ethical and existential dimension of history can only be appreciated by dissolving Oakeshott’s absolute distinction between the practical and the historical past.