Introduction Under contemporary pressures of globalisation the Caribbean Community (CARICOM)2 seems threatened by increasing global and regional insecurity, vulnerability and marginalisation as they are seemingly once again carried across another ‘middle passage rite’ in the turbulent waves of a neo-liberal globalization. How can the region find safe passage in this contemporary cross roads marking yet another chapter in their struggle for ‘survival and beyond’? What are the imperatives for successfully navigating globalisation, or negotiating a space – if there is little to none – in order to cross-over? Do contemporary analyses and policies for regional development provide an improved or even relevant basis for small and vulnerable states to achieve competitiveness? What exactly are the preconditions for CARICOM’s success? In this paper, we explore these questions and point towards elements of an answer, which prioritises analyses about ontology, through a critical engagement of some of the existing approaches to these issues.