In 1953, the success of native doctors in converting a man into a woman made news headlines in Taiwan. Considered by many as the “first” Chinese transsexual, Xie Jianshun was also frequently dubbed as the “Chinese Christine”—an allusion to the contemporaneous American ex-G.I. transsexual celebrity, Christine Jorgenson. But besides its anatomical and surgical transformations, Xie’s sex, this chapter argues, was reconfigured by the cultural forces operating upon his body, through which new meanings of corporeality and sexual embodiments consolidated in post-WWII Sinophone culture. Within a week, the characterization of Xie changed from an average citizen whose ambiguous sex provoked uncertainty and national anxiety to a transsexual icon whose fate would indisputably contribute to the global staging of Taiwan on a par with the United States. This chapter uses the cultural politics of transsexuality to reflect on the evolving geopolitical contours of Greater China in the postwar era of transnationalism.