“How can you free people,” Earl Lovelace’s character asks in the novel Salt, “when every move you make is to accept conditions of unfreedom?” A revision of Fanon’s delineation of the social and psychological parameters of freedom versus oppression projects a dynamic along which we can evaluate how Caribbean nations have been able to survive and even triumph over the adversities of traumatic and violent (post)colonial experience. Whether through mimic men or corrupt despots, the tradition of capitulation or control through terror has characterized many post-independence Caribbean islands. Literatures emerging from Cuba, Haiti and the Dominican Republic elucidate the “truths” of the homeland—either articulated by the migrant gaze back or the subversive voice of those who remain at home. For writers such as Edwidge Dandicat (Haiti), and Renaldo Arenas (Cuba), exile is a place of social and psychic mediation, contrasted to Lovelace and Fred D’Aguiar for whom the homeland remains a place of enduring loyalty and inspiration, which generates rather than stifles freedom of the mind. Yet these writers raise problematic issues of past and present disturbance and concern (ranging from reparation to eco-terrorism), whether voiced through humour, satire, or social realism. Individuals stake their claims for freedom—ethical, political, psychological, religious and social—and the right to uphold what is it to be human. How far do these conditions of freedom/unfreedom challenge Fanon’s vision of a world freed from the shackles of U.S./European hegemonies? This paper will conclude by proposing new parameters through which “freedom” should be defined.