This study comprises a comparative analysis of the counter-discourse of the Cuban poet-slave, Juan Francisco Manzano, and the Irish writer and historian, Richard Robert Madden, who championed the rights of Blacks in Jamaica and Cuba. Key figures in the history and literature of their respective countries, their literary and historical contributions have not received critical attention from the standpoint of postcolonial theory. Focussing on ambivalence, a feature of the colonized subject's discourse, this contrapuntal analysis reveals a distinct convergence in the interaction of these figures with nineteenth-century imperial culture. Drawing on primary research conducted at Leabhairlann Náisiúnta na héireann, (the National Library of Ireland) the Royal Irish Academy in Dublin, the Biblioteca Nacional José Marti (National Library) in Havana, Cuba, and using postcolonial theory as methodological framework, the analysis recuperates voices drowned out by the colonial enterprise, and may be viewed as an attempt to extend current modes of postcoloniality. Chapter One sets out the general methodological framework based on postcolonial theory. Chapter Two provides the historical perspective to nineteenth-century imperialism as imposed on Cuba and Ireland. Chapter Three investigates the complexity of identity for subjects of religio-racial oppression. Chapter Four examines resistance, where the experience of the Cuban slave parallels that of the indigenous Irish subject; the emancipation phase is viewed in relation to the struggles of Frederick Douglass and Daniel O'Connell. Chapter Five concludes the work with a synthesis of Madden and Manzano's counter-discursive strategies vis à vis the legacy of colonialism in their respective countries.