This dissertation is a case study of Ulane v. Eastern Airlines (1983/84), a historically significant and precedent setting Title VII civil rights case with a transsexual plaintiff, Karen Ulane. This study employed narrative analytical and creative analytical methodological processes in order to better understand narratives and counter narratives about Karen Ulane’s sex/gender in Ulane v. Eastern Airlines. These methodological modes allowed me to appreciate how the stories in Ulane relate to established narratives and counter narratives about transgender people in and out of the workplace. An analysis of the materials associated with Ulane v. Eastern Airlines (e.g., court transcripts, depositions, medical exhibits, news articles, transgender publications, and audio-visual material) provided the opportunity to examine a number of narratives present in the case. My analysis revealed that toxic cultural tropes about transsexuals fed into negative assumptions about Karen Ulane in the workplace. I engaged with narrative constructions and co-constructions of sex/gender in the legal arena by analyzing a subset of core themes drawn from the Ulane case materials. This project considered medical narratives related to the case through an examination of Ulane as “patient,” Ulane’s agentic behavior, characterization of transsexuality as illness and medicalization of trans identity, medical authority (who gets to be one?), “transsexuality” as defined by medical professionals, normative assumptions, and privacy (or lack thereof). Finally, this project looked at the medico-legal perpetuation of the system of binary sex/gender. Judicial opinions by the lower court and the appellate court in the matter of Ulane v. Eastern Airlines demonstrate how two courts decided very differently, yet both adhered to the notion of binary sex/gender while doing so. This is problematic because the persistent mischaracterization of trans persons as deceptive, predatory, freakish, and comical is animated by a binary conceptualization of sex/gender in heteronormative social settings, such as the workplace, where the constructions impact transgender people’s life chances and well-being.