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Turning to the legal and social history around the theft and circulation of the popular WWII calypso tune “Rum and Coca-Cola,” this chapter explores US militarization in the West Indies and its reciprocal social, political, economic, and cultural effects. Specifically, this essay illustrates how the history of US-Trinidadian relations during the Second World War thickens our perception of island-continent interrelations, and worries a tradition of American continentalism that narrowly reads islands as isolated, peripheral, and ancillary. The circulation and social history of this stolen calypso tune do more than place in relief US militarization efforts and longstanding practices and commitments to empire building in the Antilles: they focalize a turn in US geopolitics and national defense strategy away from isolationism and toward an understanding of the world as a global theater of potential threat against US safety and interests. This geopolitical turn effectively underscores the fiction belying continentalism—continents are vulnerable.

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