From the global wars on drugs and terror to the ‘Paradise Papers’ scandal, the Commonwealth Caribbean has been discursively stigmatised as a mythical island paradise of ‘rogue’ States. Not infrequently, their exercise of regulatory self-determination has been reduced to the selling of their economic sovereignty to facilitate shady business deals and financial crimes. Resultantly, these small jurisdictions have been subjected to coercive and intrusive extraterritorial regulation and surveillance within the transnational legal order for combating money laundering and the financing of terrorism and proliferation (TAMLO). Adopting a Constructivist epistemological lens, the study historicises and deconstructs these hegemonic discursive practices since the 1980s. It critiques how powerful policy elites such as the Group of Seven (G7), the Organisation for Economic Cooperation and Development (OECD), and the Financial Action Task Force (FATF) have deployed highly politicised labelling practices along the ‘Onshore/Offshore’ axis. It empirically traces how these discursive practices have constituted, normalised, and reproduced narratives of Commonwealth Caribbean States as among the ‘weakest links’ within the TAMLO, while simultaneously foreclosing critical engagement with the latent geopolitical interests and legitimacy claims of powerful onshore regulatory elites. It is compellingly argued that these discursive practices have been both constitutive and causative of the precarious diminution of Commonwealth Caribbean States’ sovereignty, exclusive AML/CFTP regulatory autonomy, and right to legitimately determine their sustainable development trajectories. Using the Bahamas, Jamaica, and Trinidad and Tobago as primary sites of analysis, the thesis substantively explores the region’s legal and regulatory policy experiences within the TAMLO with respect to corrupt politically exposed persons (PEPs) and their professional facilitators, offshore Internet gambling services, and the coherence of the FATF’s risk-based approach to combating money laundering (RBA) in developing country contexts. The study’s primary contribution to existing scholarship lies in its advocacy for the reconstitution of the transnational AML/CFTP regulatory discourse as development discourse. This anti-hegemonic stance is proffered as a potentially pragmatic solution for reaffirming the sovereignty and sustainable development of Commonwealth Caribbean States within the TAMLO. In this regard, the United Nations 2030 Agenda for Sustainable Development and Sustainable Development Goals (SDGs) have been posited as a principled basis on which to reconstitute the TAMLO as a more just, democratic, and anti-hegemonic project.