This thesis takes a transnational legal orders and ethnographic approach to the study of Cayman Islands professionals to understand how an offshore financial centre operates from the perspective of professionals who work in them. It offers a close-examination of a jurisdiction, one that is heavily referred to by critics of offshore, and brings new empirical data based on 13-months of fieldwork from a jurisdiction heavily used for some of the largest financial transactions in the world. Combined, it provides an examination of global financial transactions from a local intermediaries’ perspective in a jurisdiction considered key periphery to central economic powers. The Cayman Islands have advanced well-beyond the dog-eared pages conveying their role and reputation for being a mechanism for tax avoidance and evasion. Those inside the island offer a panoramic view of international financial activities and if probed properly, help us understand systems beyond taxation. The Cayman professional is both an example of a transnational professional in finance and a political-economic pawn to transnational professionals in onshore or metropolitan jurisdictions. Their position as being close to but not geographically or jurisdictionally linked to their clients’ onshore domicile make them a key peripheral actor, particularly in their ability to draft their own laws and regulations. Offshore professionals’ activities offer a blunt view of activities engaged in by onshore professionals who are restricted by their own jurisdiction’s financial laws, regulations and even professional codes of conduct. The key finding in this dissertation is the discovery of a trend across various sectors: the repatriation of offshore law to onshore jurisdictions and instances when onshore jurisdictions copy offshore regulations to attract business onshore. The socio-legal theory of recursivity was used to discover this process. Offshore financial centres are a testing ground for solutions to onshore regulatory problems and the most desirable results repatriate onshore.