Pigmentocracy is understood as an intertwining structuring of society based on race and social class, where lightness is afforded with a higher level of capital; in a sense, the higher up in society you go the lighter the skin colour. It is argued that the colonial history of Trinidad and its continuing legacy facilitated the evolution of an education system which embodies this sense of pigmentocracy. The result is the constitution of the dual system of prestige versus stereotyped government schools. This chapter aims to engage with the operationalisation of this symbiotic structuring of race and class in terms of access and achievement of Afro-Trinidadian primary boys in the dual system. In so doing, the legal concept of the property value of whiteness as adapted in Critical Race Theory (CRT) in education is employed. It is noted that CRT was developed in engaging with issues of race and racism in a North American and White majoritarian context. However, it is argued that the inherent fl exibility of both CRT and concepts of the property value of whiteness allows for its adaptation to the postcolonial and non-White majority context of Trinidad.