English philosopher Michael Oakeshott (1901-90) called himself a skeptic at various times, and yet his writings reveal little or no engagement with either of the major Hellenistic skeptical traditions, Pyrrhonism and Academic skepticism. Although he argued that the best way to understand ourselves is to look at the mirror of our intellectual inheritance, he did not look at this one. Furthermore, commentators on Oakeshott’s skepticism have also ignored these traditions and his possible place in them. This article explores these lacunae, (...) seeking possible reasons for such neglect in the history of the modern reception of Hellenistic skepticism. Oakeshott and his commentators may have ignored the traditions of skepticism out of ignorance, lack of respect for their intellectual acuity, or fear of their moral consequences. Finally, this article sketches some of the benefits that might have been gained if Oakeshott and his commentators had paid more attention to these traditions. (shrink)