This paper focuses on the socialist underpinnings of education policies in three small (and micro) states: Guyana, Jamaica and Grenada. It explores the role of education underneath ideological pluralism in constructing socialist citizens through cooperative socialism in Guyana, democratic socialism in Jamaica and revolutionary socialism in Grenada. The successive disintegration of ideological pluralism in these three countries paved the way for post-socialist transformations regionally as CARICOM members found solace in regional integration and the creation of the Caribbean Single Market and Economy. With the demise of these socialist experiments, this paper considers how CARICOM, as a trans-regional regime, constructed the "Caribbean Educational Policy Space" premised upon the ideal Caribbean person to function within the Caribbean Single Market erected in 2006. (Contains 1 table and 6 notes.)