This chapter contrasts the lives of Dominga de la Cruz Becerril and Trina Padilla de Sanz, one black and working-class and the other Creole-white and patrician. It offers us a window into the contradictions within the leading anti-imperialist organization in Puerto Rico in the interwar period—the Partido Nacionalista—, thereby illustrating tensions across the broader movement against U.S. colonialism on the Island. The chapter involves a detailed description and comparative analysis of the individual lives and words of both women, their divergent experiential trajectories, and exceedingly disparate fortunes. Accordingly, it clarified how both de la Cruz Becerril and Padilla de Sanz appear in the written history and official memory of those conflicts, chiefly in the contentious 1930s debates within that island’s intelligentsia and partisan leaderships over the National Question—bearing in mind that those local elites often themselves the descendants of the previous Spanish-colonial, large-property owners. This chapter highlights how both women embodied the multiple and asymmetrical identities associated with being a Nacionalista woman, complexities integral to how la patria (the fatherland/motherland) was envisioned and fashioned in interwar Puerto Rico.