In his pioneering Caliban's Reason: Introducing Afro‐Caribbean Philosophy, Paget Henry points out that because of the region's colonial history, Caribbean philosophy is far more often found ‘embedded’ in other discourses, such as literature, than in explicit theorising. Following Henry's lead, I seek to find the philosophical ‘moral of the story’ of Voices Under the Window, the 1955 first novel of the late Jamaican writer John Hearne (1926–94), which some critics regard as his best work. In a novel with significant autobiographical elements, Hearne, a ‘high‐brown’ or ‘red’ Jamaican, recounts the story of Mark Lattimer, likewise a ‘red man’ positioned at the upper edge of the ‘brown’ stratum of the white/brown/black Jamaican social pyramid. Lattimer moves from a race‐denying attempt to ‘pass’ in World War II Britain to a Marxist social activism upon his later return to post‐war Jamaica, but is killed in a black protest riot. His tragic fate raises important philosophical questions about race, colour, class, and personal and social transformation that remain very relevant today, especially considering the failure of 1970s Anglo‐Caribbean radicalism to fulfil its revolutionary promise.