This paper presents an account of four Japanese men, three of whom had an audience with Freud and who, with differing experiences and ambitions, returned to Japan to practice and develop psychoanalysis. Only two received any formal training, and two were strongly influenced by Buddhist thought. Freud gave no clear sign as to whom to appoint as leader, leaving the situation unsettled. This may have contributed to the continuing split and rivalry between groups, a split which was not resolved until the formation of the Japanese Psychoanalytic Society for trained analysts and the Association for interested laymen in the 1950s. From the beginning the development of psychoanalysis in Japan was informed by a paradox: the need to get Freud's approval and hence appear orthodox, while assimilating some of the concepts to the dictates of the culture.