This study examines the implications of the entrance of Renee Richards, a constructed-female transsexual, into the women’s professional tennis circuit. The purpose of our analysis is to show how our culture constructs woman and produces particular notions of gender, sex, and difference by examining a case in which these ideological processes are literally enacted: the construction of a “woman,” Renee Richards, from a man. We do this by exploring the cultural meaning of transsexualism in the U.S.; by examining critically how issues of transsexualism, sex, and gender are framed by the media in the Renee Richards case; and by exploring the particular problematic posed by Richards’ entrance into the highly gendered world of professional sport. Although Renee Richards appears to challenge fundamental cultural assumptions about sex and gender, closer analysis reveals that the various media frames invoked to explain the meaning of Renee Richards reproduce rather than challenge dominant gender arrangements and ideologies.