Dissertation Abstract "A Tragedy of Success!" is a close engagement with the ongoing artistic turn to Haiti and its revolution within the Caribbean literary imaginary. It argues that twentieth and twenty-first writers of the region are drawn to the nation and its Upheaval precisely because the striking incongruity of Haiti's revolutionary past and postcolonial present vividly discloses how the modern Caribbean experience is profoundly shaped by the ceaseless play of radical change (conquest, colonialism and anti-colonial revolution) and debilitating communal crisis. This project joins the rich conversation on Haiti, modernity and the Revolution begun by C.LR. James, and continued by Nick Nesbitt and Sibylle Fischer, to address this discussion's slight attention to the abundant literary production inspired by the Revolution. This dissertation therefore focuses on the ideological work of the Revolution's repeated narration in the Caribbean, specifically, the manner in which it arouses anti-colonial aspirations. It argues that the Caribbean experience of modernity has introduced a tragic mode into literary representations of the Upheaval, causing regional writers to depict the immediate as confounded by the past. Characterized by a subtle wavering between tragic pathos and comic elation, iii this mode is as much an engagement with time and its affective oscillation as it is a politics of possibility. It speaks strongly to the writers' longing for total decolonial liberation region wide. This project participates in the rethinking of tragedy, as initiated by contemporary scholars like Rita Felski, Timothy Reiss and David Scott, in order to gauge how Caribbean writers use Haiti to negotiate the difficulties and successes of the region in their efforts to portray their desire for an improved Caribbean future. iv