The proposed paper focuses on a cadre of eighteenth-century Irish exiles who fled British colonial rule in Ireland for the opportunity to become imperialists in their own right within the Spanish Empire, most spectacularly in the Gulf Coast borderlands of North America, including Cuba. Using a number of case studies, it highlights how these men empowered themselves and found their own independence by denying it to others. Whereas they were excluded from the British Empire, their supposed Milesian-Spanish ancestry, enabled them participation in the Spanish Empire. This paper will offer brief sketches of the following case studies: Ricardo O’Farrill, one of Cuba’s earliest and richest sugar plantation owners and mass slave-traders; Alejandro O’Reilly, the preeminent military reformer of the empire responsible for improving Havana’s defenses and also governor of Spanish Louisiana where he crushed a French Creole rebellion; Hugo O’Connor, captain-general and governor of Texas where he led a war of expulsion and enslavement against the Apache; Arturo O’Neill, captain of the Hibernia Regiment in the Spanish siege of Pensacola (1781) and subsequent governor of West Florida; and, Sebastion Kindelny O’Regan, slaver and governor of Santiago de Cuba during the Cuban “sugar revolution.” Not only do these Irishmen matter for their profound importance for the history of North America, Cuba, Ireland, and the British and Spanish Empires but, furthermore, they provide compelling insight into how the subaltern – if, when, and where they can- is fully able to appropriate systems of oppression for their own empowerment.