In Trinidad, a pigrnentocratically structured postcolonial society, public discourse on race and education often simplistically labels Afro-Trinidadian boys as the lowest academic achievers. Stereotypical views, reminiscent of deficit thinking models, situates blame in deficient cultural values and single female headed homes; issues viewed endemic in the typically darker skinned working class. In challenging this pathological construction, an innovative theoretical approach is adopted, one which is premised on an epistemological understanding of human experience as inseparably intersectional and socio-historically contextualised. This approach marries both Critical Race Theory (CRT) and Bourdieu's concepts of habitus, capital and field. This theoretical hybrid enables a symbiotic analytical platform able to appreciate both structure and agency; thus allowing for situational identity to be understood as within the context of wider socio-historical processes of race, class and gender, evident in the legacy of colonialism. Operationalised through a qualitative approach, data on key interrelated areas of race, masculinities and social class were collected at two Trinidadian primary schools. One was publicly acclaimed as a centre of excellence and the other stereotyped as a typical failing urban community school. A sample of Afro-Trinidadian boys, their parents, teachers and principals constituted the research participants. The emerging picture refutes deficit models, emphasizing a pigmentocratic discourse embodied in differential school ethos, teacher perception and pedagogical practice. Similarly, the re-imagining of the role model debate challenges the simplistic arguments levied against underachieving minoritised groups of low motivation and aspirations; instead, identity formation is posited as a more complex process. Equally, the operationalization of what I term `racialised facilitative capital' contradicts deficit models which blame deficient capital in failing minorities. Alternatively capital is centred as a racialised process of politic,where the capital of dominant groups is constructed as superior and that of minoritised groups as inferior; ultimately reflective of racialised achievement patterns.