From 1904 through the 1930s, U.S. corporate and military entities effectively monopolized wireless communications/radio throughout the Caribbean and Latin America, with the exception of Mexico. These stations attempted to colonize what could be heard, by whom, and on what terms. Building on a nineteenth-century infrastructure that I traced in earlier work, this paper reframes “rhythmic migrations” across Hispaniola and Cuba as a counter-plantation history of sound under U.S. occupation and corporate agriculture. In dialogue with Tao Leigh Goffe, Alejandra Bronfman, Sergio Ospina Romero, and Ana María Ochoa Gautier, I develop the concept of a “radio-plantation complex” to track how radio functioned as a territorial technology that managed commodity extraction, from sugar to songs. Alongside its military and logistics applications, radio and recorded sound enabled an extractive aural pipeline that became a profitable distribution system for commodified musical products as well as a key node of U.S. propaganda. Yet these systems did not produce passive audiences or derivative forms. In Haiti, Cuba, and the Dominican Republic, occupation-era and post-occupation musical ensembles creolized imported formats into local grammars. In particular, these artists’ engagement with “jazz” contested its projection as an imperial soundtrack and produced nuanced expressions of aesthetic self-determination. I trace several case studies, such as Cuban trumpeter Julio Cueva and Haitian saxophonist (of partial Dominican parentage) Nemours Jean-Baptiste, to show how a regional mobilization of cultural labor transformed wireless communications and jazz-era aesthetics through mutual-aid benefits, re-creolized genres, and transnational, anti-imperial mobilizations over the airwaves. I argue that, in their fight over the political economy of pleasure, these artists force us to expand and challenge the aesthetic boundaries of jazz, reclaiming its Afro-diasporic routes and creating a kind of public sphere based in a decolonial and anti-fascist popular front. In contrast to a top-down reading of U.S. radio hegemony, these artists suggest that the very attempts to render the Caribbean an economic periphery made it a crucible of technological and cultural modernity in the mid-twentieth century.