This chapter explores the subject of ruptures, taking as a number of differing perspectives that are, in fact, deeply interwoven. Thinking independently, Donald W. Winnicott made an extraordinarily creative and original effort to bridge the classical elements of Freudian psychoanalysis and the innovative ideas proposed by Kleinian thinking. The therapeutic encounter with patients who are seriously harmed at this level has inevitably led psychoanalytic research to focus its attention on the importance of the construction and/or reconstruction of the mind's symbolic capacity. A diagnosis of pervasive developmental disorder was made and the child began psychotherapy, in the National Health Service. A key element of Winnicott's work was to bring together the intrapsychic dimension and the interpersonal one through the formulation of concepts of transitional space and objects. Transitional objects are created by the child in his internal reality; he then finds these objects again in external reality.