Through close reading, historical analysis, and creative vignettes, I explore how authors and artists in the Virgin Islands have responded to ongoing American colonial rule. I suggest that these Virgin Islands authors and artists challenge postcolonial sovereignty as the only available political horizon. Chapter one juxtaposes the St. Croix Labor Union’s newspaper, The Herald, with a series of historic photographs to constitute an alternative archive that places black life at the center of American imposition in 1917. Chapter two demonstrates how playwrights have mobilized the history of revolutionary labor struggle against Danish colonialism and slavery in the nineteenth century to interpret twentieth century American empire. Chapter three explores how Tiphanie Yanique’s novel, Land of Love and Drowning, represents intimacy and desire as forces that can challenge the bounds of American imperialism. Chapter four considers how the lyrics of singer-songwriter Vaughn Benjamin shift the discussion of non-sovereignty from the state to the human, offering a revitalized humanism grounded in Rastafari philosophy and non-sovereign human agency. Together, these essays suggest that the Virgin Islands is not a site of exception, but crucial to broadening understandings of Anglocreole Caribbean literature and postcolonial sovereignty.