This essay presents a sketch of what a critical genealogy of the anthropology of the Caribbean might involve. After looking at the origins of anthropological interest in the region, I will focus on two case studies that, for better or worse, may be said to have had lasting diagnostic value for key epistemological orientations in Caribbeanist anthropology. I do so by examining M. G. Smith's Plural Society model and Julian Stewart's Puerto Rico Project in their Cold War contexts to point out why these truly pathbreaking endeavors resulted in a vision of Caribbeanness that we may well want to rethink.