This paper addresses the notion of irrationality and madness, as they are understood within the psychoanalytic framework. By highlighting their similarities and differences, as well as by emphasizing the crucial defensive position that manifest psychosis holds in the midst of all this, an attempt is being made to delineate the links between the conjectured earliest interaction that the infant has with its environment and the burgeoning conscious rational mind. Winnicott's conceptualizations around fear of breakdown, disintegration, the environment-mother, and therapeutic regression are utilized to form a bridge between the theoretical understanding of madness and the clinical applications of this understanding, as illustrated by a clinical vignette.