Winnicott’s paper, “Playing, Creativity, and the Search for the Self,” Chapter 4 of Playing and Reality is the second leg of Winnicott’s two-part opus on play. It is the focus of Smadar Steinbock’s essay on temporality in the work of Winnicott and Loewald. Winnicott’s is a paper fundamentally about play. I suggest that for Winnicott, play always involves time, specifically the actual or feared loss of time or object, namely what I have referred to as the play of mourning. For Winnicott, temporality is inextricably bound with his notion of place. And they are both contained in the analytic setting. This is a setting that allows for the emergence of play and creative experiences of self, in time in general and for the time being. Like so many phenomena in Winnicott’s theory building, time involves both actual or real time and time as incorporated psychically into the realm of illusion. Chapter 4 puts forward the ways that patient and analyst hold the paradox of time as actual and as incorporated into the realm of psychic illusion in order for the patient to be found.