Transnational citizen and athlete Sydney Maree’s life story, like many personal histories, reveals the lived experiences of larger political and cultural shifts. Drawing from an in-depth interview with Maree, I develop the theoretical framework for a critical biography using Critical Legal Studies (CLS) and postcolonial theorist Gayatri Spivak’s concepts of the subaltern and catachresis. In particular, I apply the notion of catachrestic history as developed by historian Tani Barlow to explicate the historical, political, and cultural contexts which condition Maree’s personal story and within which his life can be understood. In order to make a case for catachrestic history, I highlight the useful ways critical biographies have developed within CLS, examining the ways notions of the subaltern and catachresis extend and more fully develop this project. Rather than provide a chronological account of Maree’s life story, I offer brief critical examples of his experiences, as an example, ultimately, of catachrestic history.