In this paper, the author revisits Stephen Mitchell’s important developmental tilt hypothesis in light of his treatment of Winnicott’s most creative contributions to psychoanalysis. It is the author’s contention that neither Winnicott’s focus on play as the central factor in the therapeutic action of psychoanalysis nor his role, along with Bion, of creating an ontological turn in psychoanalysis were accounted for in Mitchell’s reading of Winnicott. The author argues that in Mitchell’s useful attempt to redress some of the ways that regression had been concretized in psychoanalytic practice and theory, he overlooked Winnicott’s complex view of holding and the mutual elements of regression that occur between patient and analyst in play. Play embodies tensions between the symmetrical and asymmetrical elements of the analytic relationship in ways that Mitchell did not consider in his developmental tilt hypothesis.