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The evacuation of British children during World War II is read alongside the legend of the ‘Pied Piper’ after which the mass migration was officially named. While virtually every British account of World War II makes mention of the evacuation, most are silent on the question of its ominous title: ‘Operation Pied Piper’. This paper traces the legend's key theme - on influencing and being influenced - as it surfaces in the writing of one child analyst and one social worker charged with the responsibility of leading a family of five hostels for British youth. At a time when Hitler's deadly regime reached unprecedented heights across the Channel, the legend of the ‘Pied Piper’ becomes a highly suggestive metaphor for thinking about D. W. Winnicott and Clare Britton's writing on what authority could mean in the face of leadership gone terribly wrong. Quite another, profoundly intimate loss of leadership haunts their words as well: Sigmund Freud, in exile from Hitler's Europe and leader of the psychoanalytic movement, died in London just weeks after the first wave of Blitz evacuations. It is in this context that Winnicott and Britton articulated a theory of authority that could address the losses of history without at the same time demanding the loss of the mind.