This essay explores the ways that new judicial formations centered on the Caribbean Court of Justice provide a space for understanding the workings of various legal rights brokers as central to a project of Caribbean regionalism. It examines the intermediary spaces in which legal brokers—predominantly nationals of countries in the region—are reconstructing legal regimes through which new spaces of Caribbean regional unity are taking shape. The development of such formations further accentuates the need to understand the particularities through which new regionalisms underlay old forms of social organization and, thus, are becoming relevant in the ways regions are being reinscribed in increasingly international spheres of engagement. The agents engaged in such spheres of international and regional governance are transforming juridical structures in the Caribbean. These changes are taking place not simply through the workings of national institutions, such as schools and cultural life, but also through the circulation of assemblages of judges and lawyers, leaders, international nongovernmental organizations, and consultants who provide a certain level of expertise toward regional integration. What characterizes this formation is not just its judicial structure but the politicians, experts, and judges who function in the advancement of a particular social cause. The mobility of these actors and the products of their knowledge mark an important change in the political organizing that has accompanied and facilitated the massive decentralization of capital accumulation worldwide. What distinguishes this Caribbean-basin form of regionalism from earlier forms is its dream of membership in the international community and its brokers' circulation on the world stage. These brokers, experts of sorts, travel from region to region. This article interrogates how to make sense of the emergence of these cosmopolitan brokers in relation to locations historically imagined as the Caribbean.