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We tend to focus on the optimistic version of Winnicott’s theory of play in which playing designates a creative experience that enables the subject to discover a novel relationship to the world in a natural and transferential way. In this view, playing is therapeutic in and of itself. Without refuting this aspect, the present paper examines another aspect of play that is less “radiant.” After discussing the extent to which the positive experience of playing dialectically assumes the negativity of the experience of formlessness, this paper studies two games which, in Playing and Reality, go against the theory of play: the “boy with a string” and the “woman playing patience.” A tragic dimension with clear implications for current clinical work with children is thus brought back into Winnicottian thought.