It has long been argued that the English-speaking Caribbean states require the establishment of some kind of effective and binding regional system of governance. What is more, the many deficiencies of the current system are widely known and acknowledged. Why, then, have they not been seriously addressed over a period of more than 40 years? This paper argues that the key blockage is the continued adherence of Caribbean political leaders to a conception of sovereignty and statehood that is inappropriate and outdated. These are no more than constructed concepts that have been framed and deployed differently in other parts of the world, notably in Europe. The conventional Caribbean understanding of sovereignty and statehood needs urgently to be opened up, unpacked and discussed in a frank and open debate with the people of the region. The paper sets out a series of steps by which the region’s leaders can initiate and lead such a debate prior to designing a new set of governance arrangements for CARICOM that would permit the substantive strengthening of sovereignty via its creative pooling. Only when a more nuanced and sophisticated understanding of what sovereignty means in the contemporary world order is embedded into the Caribbean political culture will the leadership be able to build the effective institutions of regional governance that remain so badly needed.