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“Playing is itself a therapy,” argues Winnicott, in one of the most famous phrases in the history of psychoanalysis. Despite its seductiveness, this paper suggests that this powerful proposition should be reconsidered. Winnicott’s extraordinary ability to transmit his theory in jargon-free language should not conceal the singularity of his conception of playing. Questioning the triad of play/playing/game may, therefore, be theoretically illuminating and clinically constructive. After examining (1) the stumbling blocks of Winnicott’s concept of playing and the negative part implied by its dialectics, this paper will highlight (2) the markers Winnicott offers us to identify the reasons behind some failures he noted, and (3) their consequences on the reception of play activity in the cure. This will lead us to propose a discontinuity between the play activity phenomenologically speaking (what we call “play”) and what Winnicott defines as the event of discovering the self through creative experience (what he calls “playing”) in order to rethink the question of what is “therapeutic.” Our conclusion that “some types of play without playing may also have a therapeutic function” will show the distance travelled in relation to Winnicott’s initial proposition.