As indicated by the title of this chapter we are once again moving into Winnicott’s universe in order to use his concepts to reconnoitre psychopathology on the border. Winnicott’s name will always be linked to the concepts of the transitional object and of potential space. The concept of the transitional object has added a psychoanalytic term to the general experience of the very young child’s particular use of teddy bears and ‘blankies’. In adding the concept of potential space Winnicott has not only found a useful way to articulate a previously known phenomenon, he has created what may be one of the most important concepts in recent psychoanalytic literature. He termed this potential space a third area, thereby contributing to healing the split between the internal and the external, between subject and object, which has dogged western thought since Descartes (Turner 2002). However, Winnicott himself was not entirely satisfied with the way in which his contemporaries understood and used these concepts. As early as the time of the first publication of the concepts of the transitional object and transitional phenomena in his 1951 article of the same name, Winnicott specified in a footnote that he was not referring to specific objects, but to a quality inherent in the child’s way of using them. In 1971, when he published Playing and Reality, he pursued this point with additional comments to what he must have perceived as misunderstandings of these popular concepts.