“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.