This dissertation examines the relationship of skepticism and philosophy in the work of G.W.F. Hegel. Whereas other commentators have come to recognize the epistemological significance of Hegel's encounter with skepticism, emphasizing the strength of his system against skeptical challenges to the possibility of knowledge, I argue that Hegel develops his metaphysics in part through his ongoing engagement with the skeptical tradition. As such, I argue that Hegel's interest is not in refuting skepticism, but in defining its legitimate role within the (...) project of philosophical science. Hegel finds that historical forms of skepticism have misunderstood their own activity and thus have drawn the wrong conclusions from the epistemological challenges that they raise. For Hegel, these challenges lead not to the suspension of judgment, as many skeptics have assumed, but to an insight into the fundamental nature of reality itself. For this reason, I argue that it is important to distinguish between historical forms of skepticism (e.g., Pyrrhonism) and the "self-completing skepticism" that Hegel describes in the Phenomenology of Spirit. It is the latter sense of skepticism, I argue, that one finds at work in Hegel's own philosophical project at nearly every stage of his career. (shrink)