This research seeks to understand the outcome of decades of education reform initiatives in the West Indies. Utilising the Qualitative Document Analysis (QDA) method, official public documents were collected through web and catalogue searches. Dominant themes were identified through manual and electronic coding using MaxQDA software. These emergent themes were examined through the lens of the edutocracy and elite theories to provide more in-depth analysis of this research problem. The document analysis constructed a narrative of how colonial ideology embedded within the inherited West Indian educational system runs counter to the progressive and more humanist visions and missions envisaged for present-day Caribbean education, culminating in deleterious conflicts between educational theory and practice. This work therefore concludes that there has been little substantive Caribbean education reform owing to the significant gaps between early twenty-first century, and even earlier drafted education visions, and current education practice.