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D. W. Winnicott's construct of the transitional realm of human experience has been widely applied and creatively extended since its introduction more than half a century ago. The author describes the extension of this construct beyond its roots in the phase-specific need for the transitional object to a paradigm for psychic structuralization. He then considers a larger implication of this construct as an organizer and vehicle of transformation in analytic process via the transference. In this more elastic use of Winnicott's construct, the analytic process becomes organized along the lines of the earliest transitional experiences: the developmental progression from a nascent to a separate self, the organization of drive experience via the other, and the sorting out of one's own mind in terms of subjectivity and objectivity. Transitional organizing experience is used as shorthand for these far-reaching structural and dynamic transformations that take place within and between patient and analyst in the dyadic interplay of the analytic process. Via familiar dynamic constellations that emerge within the analytic process, the analytic dyad comes to reexperience (as a 2-person psychology) and reorganize (as a 1-person psychology) toward less “pathological” transitional forms of experience, allowing for a resumption in development of creative transitional space.