In this article I discuss the phenomena of transgender in Freudian terms and advocate a position that avoids collapsing it into diagnostic categorizations. My reading of the relevant Freudian texts construes their core assumptions in a way that highlights their diversion from the normative context in which they were formulated. I illustrate my reading by presenting a detailed clinical case, focusing on the tensions between the inherent heterogeneity of Freudian sexuality and the personal and social demand for homogeneity and coherence. Using Freud’s late formulations of psychic conflict, I argue that the suffering associated with trans phenomena cannot be explained or treated by addressing only the misalignment between gender and anatomy. Both must grapple with the intense presence of the death drive, with its derivative destructiveness and aggression, in the arena of gender.