Much has been written about the challenges facing CARICOM as a result of the liberalization, globalization and integration phenomena. This paper adds value to the conversation by addressing the nexus between and among economic asymmetries, trade liberalization and economic integration, as it relates to CARICOM as small developing economies. The paper seeks to highlight the salient issues of CARICOM economic adjustment challenges under trade liberalization and integration imperatives, particularly as they may be subjected to the constraints of economic asymmetries. In doing so, it steps away from the conventional approach of reciting a series of data usually associated with the issues and instead, engages in commentary and assessment regarding the changing economic landscape in the Region and elsewhere. The issues are indeed very complex and the arguments and conclusions flowing from this type of evaluation may not be in lock-step with the conventional wisdom. However, it is our contention that the regional trade and development policy solutions does not lie in denial of the existence of the problems; but rather, in tackling them head-on and incorporating them into existing and proposed systems of economic relations.