Despite pedagogical, technological, and curricular advancements in the West Indian education system, there has been little success in constructively addressing the pervasive regional English language examination failures. I contend that most researchers address these second language acquisition failures by focusing on symptoms rather than causes. However, this study seeks a novel way of tackling the problem, by employing the WordTree design by analogy method, typically used in the engineering field, but adapted for this social science enquiry. The method is used to generate a fitting analogy for the current failing language education system to provide insights into underlying issues, which assist in better understanding and addressing this failure. This method finds that the failing system is analogous to that of the plantocratic system of colonial times based on their strikingly similar ideologies, practices, and attendant outcomes. Resultantly, I term this language education system, an edutocracy. This study expands on scholarly works in the advancing areas of curriculum as cultural practice and colonial imagination to provide a different, deeper perspective of this West Indian problem, while exploring the implications of the analogous relationship.