The history of European overseas expansion has traditionally been studied from a national perspective. However, the rise of Atlantic history, global history, and a revitalized maritime history has prompted scholars to question the rigidity of Early Modern borders assumed by these conventional national or imperial frameworks. In parallel, researchers have contested the state-centric viewpoint by advocating for an actor-focused approach to Atlantic System history, emphasizing the role of private merchants and their informal, international networks. These approaches have uncovered the involvement of entrepreneurs belonging to polities without a formal empire in the colonial ventures of other nations. This paper examines one such trans-imperial enterprise: Romberg & Consors, a firm operating from the Austrian Netherlands. During and after the American War of Independence (1775–83), Romberg & Consors leveraged evolving Spanish attitudes toward the slave trade and the establishment of neutral trade to organize slave trade expeditions to Cuba. By closely analyzing the operations of this Imperial firm, this study illuminates a decisive phase in Spanish imperial history while contributing to the often-overlooked Atlantic history of the Habsburg Monarchy and the Austrian Netherlands.