The author presents the result of a quantitative survey as a part of a larger mixed-methods study conducted across two case study schools in urban Jamaica. It focuses on Black Caribbean boys' levels of educational aspirations in relation to their economic, social, and embodied cultural capital. The study utilizes Bourdieu's notions of capital, reconceptualized to match the sociocultural context of the research and set within a critical realist metatheoretical framework. Logistic regression models, supported by participants' narratives, show boys' educational aspirations to be highly predictable by their level of capital-including dispositional beliefs held through influence of the maternal family both locally and in Jamaican diaspora of the United Kingdom, United States, and Canada.