This paper uses a Cultural Political Economy (CPE) framework to apply CPE's concept of the "economic imaginary" to the educational policy landscape. We consider the Caribbean Community's (CARICOM) regional education policy space and the focus on Human Resource Development to examine how what we call "educational imaginaries" develop and evolve as a product of intersecting interests, power hierarchies, discourses, and material realities. This paper draws from education policy documents developed by formal regional governance bodies within CARICOM between 1993 and 2021. Using CPE's four selectivities (discursive, structural, agential, and technological) to examine the construction of the CARICOM educational imaginary, this paper ultimately demonstrates how CARICOM responds to global hierarchies as a regional entity.