ABSTRACT This article interrogates transhistorical layers of colonial violence, and resistance to it, linked to the island of Navassa, located off the southwestern coast of Haiti. Long the subject of territorial disputes, the island and its literary entanglements point to the interconnectedness of resistance to colonialism by subalterns in the circum-Caribbean. To illustrate this, I analyze, among other texts, a sixteenth-century Spanish colonial account of a canoe journey, a nineteenth-century benevolent society pamphlet written in defense of revolting miners of guano (fertilizer made of avian excrement), a North Carolina mayor’s twentieth-century local history project, and a twenty-first-century narrative by ham radio hobbyists of an expedition to the island. Ultimately, I identify thematic continuities and argue that Navassa Island and its entanglements signify as synecdoche for the (anti)colonial hemisphere, an observation which has repercussions for how we understand the semiotic charge of individual islands and their respective historiographies.