This essay attempts to provide a historical account of Michael Oakeshott’s famous distinction between civil and enterprise association. As such, it demonstrates that Oakeshott’s political skepticism and his concomitant view of civil association can in part be explained by his reliance on Augustinian theology. In a similar vein, Oakeshott’s linkage of enterprise association with the rationalism of Bacon must be considered in terms of Oakeshott’s understanding of Pelagianism and Gnosticism. Unsurprisingly, it will be demonstrated that despite Oakeshott’s disagreements with the (...) political philosopher Eric Voegelin, he was very impressed by Voegelin’s work on the Gnostic origins of modernity. Consequently, a major claim of this essay is that Oakeshott’s speculative understanding of modern political thought constitutes a theological genealogy of political modernity in all but name. (shrink)