This essay brings together four artist-activists of the Caribbean and Pacific under the archipelagic auspices of the “Mediterranean of the West,” a term coined by Jamaican nationalist W. Adolphe Roberts in his pioneering study The Caribbean: Story of Our Sea of Destiny (1940). Roberts’s Mediterranean opens disjunctively onto anticolonial figures elsewhere: Roberts’s fellow West Indian C. L. R. James as well as the “fathers” of Cuban and Filipino independence, José Martí and José Rizal. These four anticolonialists are case studies in resistant comparison, seemingly ready-made but difficult to track: Martí and Rizal, writing in Spanish on behalf of the modern Cuban and Philippine nations during the twilight of the Spanish empire, and James and Roberts, writing as English-speaking West Indies nationalists a half century later in the context of postwar decolonization. The essay focuses on language politics, the relation of language to the colonial and national situation in the transnational, translingual histories linking the Caribbean and the Pacific as outposts of the Spanish empire at its end and the American Century at its beginning.