Inspired in part by a paper in the British Journal of Psychotherapy by the psychoanalyst Malcolm Pines, describing the Cambridge and Bloomsbury background of the psychoanalyst, Adrian Stephen, in this paper I draw on the writings of his older sister, Virginia Woolf, and on other data as means of highlighting and explaining aspects of his life and work. In particular, I discuss his rebellion against their father, Leslie Stephen; his subsequent rebellion against authority before and during the First World War; and his involvement in psychoanalysis and politics during his medical and psychoanalytic training in the 1920s. I go on to explain how his opposition to tyranny informed his approach to psychoanalysis as means of freeing patients from the control exerted over them by their phantasies. And I show how, during the Second World War, he resisted dominance by Ernest Jones and Edward Glover of the British Psycho-Analytical Society, and how in his post-war clinical work he extended Freud’s moral version of the super-ego into an account of it as a wish-fulfilling agency of the mind.