In this study I contend that formal equality of opportunity is a political myth that drives underrepresented groups into acquiescence and passivity. To do this I will compare Jamaica and the United States, two countries steeped in a similar history of chattel slavery and common patterns of framing educational opportunity. I posit that a common history of symbolic manipulation though affirmations of formal equality of opportunity served to promote inertia in the hearts and minds of poor Afro-Jamaicans and Afro-Americans. Educational policy is the primary lens through which I will attempt to assess the impact of formal equality on the actual opportunities afforded to Black people in Jamaica and the US. Despite the so-called gains of ‘equality under the law’, educational disparities are in many ways just as, or even more salient than in the Civil Rights era in the US and in pre-Independence in Jamaica because of the sheer lack of opportunities for these underrepresented groups. Through systematically assessing the history of educational legislation and jurisprudence in the US and Jamaica, I will demonstrate the coercive power that symbols have to manipulate individuals most disadvantaged by them. If Jamaica and the US have made such inroads to equality why do things remain so eerily similar to more shameful times in the past? In Jamaica and the United States class and racial struggles have started to evolve in more subtle ways that repress the underrepresented and it is the aim of this study to track the when’s, how’s and why’s of these manifestations of inequity. Only through understanding these dynamics we can perhaps identify ways of opposing them.