Today, colonial literary models are joined by mid-twentieth-century anticolonial and postcolonial models, and combine to constitute a rich archive from which Caribbean writers can draw in order to make sense of the region’s position within global capitalism. The texts considered in this essay demonstrate contemporary writing’s sustained commitment to rewriting the earlier texts that have shaped the region’s writing from the beginning, but now in a manner that self-reflexively considers its own regional literary canons in autointertextual ways. This chapter shows how contemporary writing develops trans-textual and trans-historical networks across generations and histories in order to engage with the possibilities for reconciling colonial and postcolonial history, in ways that can make sense of the present. Moreover, this essay also highlights how it does this through formal experiments with Caribbean literature’s own genealogical entanglements.