Waves of early twentieth-century Asian migration to the Caribbean and Afro-Caribbean migration to and from Panama bankrolled the education of a new black and brown middle class. This essay argues that we can hold more of the Caribbean literary tradition within a single frame if we reconfigure the archive so as to highlight the moments when the educational advances the concurrent migrations facilitated allowed both African and Asian Caribbean communities to exert greater control over the terms of their representation. It advances three approaches to rethinking Caribbean literary history. The first examines how early twentieth-century Caribbean fiction represents both groups’ changing attitudes towards money and modern subjectivity. The second considers how migrants’ counterintuitive investments in imperial expansion complicate the political stakes in Caribbean nationalist narratives. The third juxtaposes literary and non-literary forms of cultural production in Jamaica and Panama to demonstrate how, in privileging written texts, we obscure the contributions marginalized groups make to what we think of as national cultures.