This chapter contextualizes the career of the maverick, proletarian, Chinese American writer H. T. Tsiang – both the contrarian, “floating” sensibility that led him to self-publish his work in the 1930s and 1940s, challenging the China-watching mainstream which constellated around the bestselling author Pearl Buck, as well as the renewed interest in his work decades later, when it was recast as performing a kind of avant-garde negation. Tsiang’s career offers a model for thinking about rivalry and failure, the latter-day romance of lost causes, as well as the lineages drawn upon to sustain the aspirational scope of Asian American studies.