Psychoanalysis has been confronted with the conundrum of integrating the use of psychotropic medications with the talking cure, with understandable concern about the substitution of a pill for working through. This paper addresses a unique situation in which the “pill” constitutes hormone-blocking drugs or cross-sex hormones to treat transgender youth. Clinical material of a 16-year-old transgender female is presented and followed by a review of several aspects of transgender hormone treatments. Winnicott's construct of the True and False Self is then used to argue that the True Gender Self of transgender youth is not the gender assigned to them at birth but the gender they experience themselves to be. The paper concludes by suggesting that if hormone blockers and cross-sex hormone therapies facilitate the strengthening of a youth's authentic gender self, the administration of those drugs is in the best interests of the transgender youth's healthy development.