In the debate about Michael Oakeshott’s philosophy there is very little agreement on the theoretical and historical meaning of his skepticism. Starting from the assumption that skepticism is not a fixed theory but a tradition of ideas, this article draws on both published texts and archival materials to contend that Oakeshott developed his thought by confronting himself with, and even merging, different strands of skepticism: the ancient, the modern, as represented by Hobbes and Montaigne, and the idealist, as conceived by (...) F. H. Bradley. The article firstly shows Oakeshott’s awareness of ancient skepticism, even though its impact on his thought is contested and controversial. With regard to modern skepticism, it looks at how Oakeshott defines Hobbes’s skepticism in his “Introduction to Leviathan.” It also examines the relevance of Montaigne to Oakeshott’s image of conversation, his idea of human agency and conception of politics. Finally, the article illustrates the influence of Bradley’s skepticism on Oakeshott’s conception of philosophy and reveals the consistency between Oakeshott’s skepticism and idealism. What emerges is a complex picture, in which Oakeshott’s skepticism is a constellation of elements taken from a variety of sources. (shrink)