In his extensive writings in philosophy and the history of ideas, the late Isaiah Berlin never systematically addressed Sigmund Freud as a thinker or psychoanalysis as a body of thought. Nonetheless, there are a number of areas of intersection between Berlin's interests and those of Freud. This paper seeks to review, compare, and contrast these areas, and to offer some speculations, derived from recently published biographical data, about Berlin's avoidance-neglect of this critical aspect of twentieth-century thought.