Fools and children—particularly infants and young children—proliferate in the wisdom traditions of the world. Both are outsiders to and subversive of the positive, adult male knowledge tradition. King Lear’s Fool, for example, turns out to be the only adult in whom (because he is a “child”) an old, failing king at the mercy of his enemies can find any wisdom. It is the fool who presides over the old king’s rebirth and his reassumption of childhood. As they are presented in Western wisdom discourse, child and fool stand for a crisis in human understanding of self in its relation to whole, or cosmos. Historically, this crisis originated in the Greek and Hellenistic world, where both the Near Eastern wisdom-as-technical-knowledge tradition, which had one culmination in the sophists, and its close relative, the even older Egyptian wisdom-as-harmony-with-cosmos tradition which culminated in Stoicism, fell to the radical Socratic aporia. This paper seeks to identify the psychological and epistemological moment at which child and fool become powerful, if enigmatic, signs of the hidden wisdom for the Western tradition, and significant symbols for the mythic structure of Western self-understanding.