This article sets out to theoretically explain the Caribbean Community’s (CARICOM) integrative stalemate. It argues that this needs to be studied in light of a changing regional, geographic, and geostrategic climate. A shift is occurring from ‘endogenous regionalism,’ which concentrates on the Caribbean’s historical past, to ‘exogenous regionalism,’ which focuses on creating a borderless Caribbean space and promotes Caribbeanization through the Caribbean Single Market (CSM), which came into force in 2006, and the stalemated Caribbean Single Economy (CSE). I argue that new trans-hemispheric relations are emerging and Caribbean regionalism is now both multi-centric—arising from actions in numerous places rather than a single center—and also multi-temporal. In this context, mature regionalism presages effective governance by focusing on deepening regional structures and institutional arrangements. I argue that trans-regionalism is a multidimensional process that moves away from the spill-over effects of trade policy harmonization and streamlines different political, security, economic, and cultural regimes. I conclude by suggesting that ‘meta-steering’ in the form of ‘strategic coordination’ or ‘first order response’ is but one way to perceive the paused regional project.