Joining the centennial reexamination of Freud's “Analysis of a Phobia in a Five-Year-Old Boy” (1909a), the author returns to Little Hans as the Ur psychoanalytic boy. Hans's construction and acts of consciousness continue to endow the psychoanalytic construct of masculinity with meaning. It is suggested that Freud moved in his discussion of the case to regulate the unsettled conditions of masculinity that he articulated through his clinical observations of Hans. The case is viewed as an exemplary illustration of how masculinity is foretold—a normative narrative that has changed little in the last 100 years. The author offers a contemporary view of masculinity as a dilemma of boundary—neither fully interior nor fully exterior, neither fully fantastic nor fully socially constructed.