This chapter examines Winnicott’s work on Fear of Breakdown and The Psychology of Madness. Abram proposes that Winnicott’s clinical-theoretical paradigm highlights how the deficiency of holding for the newborn infant causes madness. With reference to the work of Joan Riviere, she suggests that Winnicott was influenced by her work on the ‘negative therapeutic reaction’ but each had their own very different basic assumptions: for Riviere, following Freud, it was the death instinct and for Winnicott it was the failure of the primary relationship. With a clinical illustration in which the patient’s fear of madness was more pronounced than fear of breakdown she suggests that the negative therapeutic reaction is founded on the early deficiency in the infant’s early development and that in the context of analysis the fear is intrinsic to the concept of nachträglichkeit.