This paper considers Winnicott's critique of Jung, principally expressed in his review of Memories, Dreams, Reflections, which asserts that Jung's creative contribution to analysis was constrained by his failure to integrate his 'primitive destructive impulses', subsequent to inadequate early containment. It is argued that although Winnicott's diagnosis illuminates Jung's shadow, particularly his constraints vis-à-vis the repressed Freudian unconscious, it fails to appreciate the efficacy of the compensatory containment Jung found in the collective unconscious. This enigmatic relationship between destruction and creativity-so central to late Winnicott-is illuminated by Matte Blanco's bi-logic, and further explored in relation to William Blake. Winnicott's personal resolution through his Jung-inspired 'splitting headache' dream of destruction-previously considered in this Journal by Morey (2005) and Sedgwick (2008)-is given particular attention.