In the Republic of Trinidad and Tobago, there is a high rate of illiteracy among the populace and a high dropout rate at the secondary level of education. This evaluative case study examined the effectiveness of the adopted strategic academic education reform initiative Vision 2020. The research questions that guided this study regarded the extent to which the goals and objectives of Vision 2020 were met. Qualitative Data were analyzed using constant comparative and coding methods to identify emerging categories. The NVivo software allowed the researcher to search for common words usage, attach codes to those selected textual patterns, and develop those commonalities into specific themes. The data collected supported the notion that in the short-run, the achievement of Vision 2020 in Trinidad and Tobago is minimal and identified that the quality, access and equity to a quality education among all students were not addressed. The participants in the study consisted of parents and administrators who completed the Quality Education Survey, and agreed to partake in one to one and group interviews. The findings revealed an increase in access at the primary and secondary levels for economically disadvantaged students. However, the study also revealed a lack of technological integration, an increased alienation of parents since the changes have been implemented, and the perception among parents that teachers are focusing more on policy than on personal interactions. The Republic of Trinidad and Tobago can likely achieve positive social change, and improve the standard of living of the underserved by increasing the use of technology and developing more collaborative programs with parents so that the vision and goals of the initiative can be actualized.