This paper seeks to produce an integrative portrayal of Winnicott's singular approach to emotions, which to date is an incomplete mosaic. The findings are congruent with his more familiar approach to psychotherapy, in which he shows how therapist and patient jointly find glimmers of emotions, beckoning them towards the point where the flowing river of emotions has been blocked for the patient, negatively impacting his emotional development. Winnicott emphasizes the development of emotions which extends the emotional range and deals with its prerequisites, beginning with psychosomatic holding evolving into holding of emotions and needs. Special stress is laid upon emotions resulting from a lack of emotional holding. Winnicott's language translates that of the incommunicado self into that of the communicative self, thereby creating the paradoxes so closely associated with his writings. His emotional language reflects his approach to emotions, i.e., a quest after the vitality embodied in free emotional flow.