How in the post-colonial present do we conceptualize the societies in the Caribbean? While explicitly a formulation about meaning in the post-colonial present, this question has a deep history concerning how writers, scholars, and artists conceive of the Caribbean. The Caribbean, of course, is a subjective category for its inhabitants and interlocutors, representing distinct, and at times contested categories of analysis. By bringing these meanings and their genealogies into relief and into conversation with one another, the organizers of the seminar point to a generative opportunity for advancing work on the Caribbean in general but in particular at The Graduate Center, CUNY.