This essay comments on the emotional difficulties psychoanalytic discussion introduces to conceptualising the poesis of gender through its reconsideration of the valence of aggression and its development in psychical reality. It returns to the 1936 lectures on the emotional life of gender given by Melanie Klein and Joan Riviere to a public about to go to war. These psychoanalysts are known for representing "the mad side" of gender and consider femininity and masculinity as lending emotional weight to the body and as one source for phantasy material that propels gender's reach into symbolisation, conflicts, and intersubjectivity. Their views are brought into tension with Winnicott's reconceptualisation of aggression in gender development. While historical questions on the relation between psychoanalytic theories of gender and the context of World War II are raised, Winnicott turns to a little war in the emotional life of gender to analyse traces of mental pain that its history leaves in its wake. He raises the new problem of the play between internal and external reality and how a one-sided take on gender as either masculine or feminine as the entire experience and goal of the body forecloses attempts to understand the self's gender work as both internal conflict and intersubjectivity. Loyalty to one side, or the defence of splitting into good and bad, itself the condition for war, has as one of its roots gender polarity. The madness of lecturing on gender resides in conveying this problem. My contribution leans on psychoanalytic allegory: that a return to historical discussion of psychoanalysis on the problems of representations of gender may allow reflection on our world of war and create elbow room needed to reconceptualise the currency, difficulties, and emotional obstacles repeated in contemporary pedagogical efforts and research. (Contains 3 notes.)