This paper is based on the premise that if CARICOM’s agricultural sector in general, and more specifically the export sub-sector, is to thrive in the rapidly changing trade environment there has to be a continuous systematic assessment of market opportunities and competitiveness status. Such an assessment however, requires a clear understanding of the multifaceted concept of competitiveness and its major determinants. This paper seeks to contribute to the regional discussion of competitiveness, through the exploration of the theoretical and empirical dimensions of the concept within the context of CARICOM’s export of specialty crops to the United States. The paper uses a methodology heavily based on the Module to Analyze the Growth of International Commerce (MAGIC) software program developed by the Economic Commission for Latin America and the Caribbean (ECLAC). This programming module uses a variation of the classical and modified shift share or constant market share (CMS) analyses. Findings suggest that CARICOM, over the period 1991-2004, has generally not been competitive in the US import market for fresh (non-processed) specialty crops. Only three crops (pepper, papaya, and coffee (not roasted) exhibited increased competitiveness. However, these crops held very low market shares and exhibited the highly transient nature of competitiveness. The challenge for the Region is how to effectively move these very low market shares to higher levels within the context of transient behavior and a fierce rivalry for the US import market. .