This chapter traces the contours of Derek Walcott’s career from regional Caribbean author to English-based publishing success to relocation to the United States in the American university system. Shortly after the publication of Omeros in 1990, Walcott became the Caribbean region’s first writer of colour to win the Nobel Prize for Literature, an award associated with a wider recognition of a new Caribbean literary 'province' that had emerged in similar ways to the Irish and American 'provinces' of the early twentieth century. Omeros is an ambitious epic work that attempts to totalize both Walcott’s and the Caribbean region’s mixed indigenous, European, African and American heritages. But, like other earlier modernist epics, Omeros combines an exultant sense of literary accomplishment with anxieties of failure. As promises of new postcolonial beginnings for the Caribbean slide into visions of climate catastrophe, and as Walcott finds himself an émigré in an imperial and racist America, the poem oscillates between its affirmative and apocalyptic impulses.