As the number of transgender legal cases reaching American courts increases, a growing body of scholarship has begun to examine how judges and institutions struggle to reconcile gender variance in a system with deeply entrenched gender normativity. Scholars have examined how judges become the interpreters of gender when presiding over cases concerning transgender inclusion and civil rights, constructing narratives of what it means to be transgender and codifying it as law. This paper presents a novel systematic analysis of judicial frameworks courts use to adjudicate gender identity. Analyzing 70 court opinions from 1966 to 2022, I examine how judges rhetorically describe gender variance and gender variant people to anchor them within deeply entrenched gender normativity. Updating and recontextualizing past scholarship within the current post-Bostock transgender rights crisis, I present a typology of four categories of judicial interpretation—biological gender essentialism, medicalism, assimilationism, and deferential to the litigant—and note other rhetorical and juridical trends for interpreting gender variance. I argue that the frameworks that most likely lead to a trans litigant’s victory are ones which reify the gender binary and pathologize transgender people, and discuss the problematics of that success.