Ainsley Harriott heads to the West Indies to uncover his roots and discovers that Caribbean history is not quite as black and white as he had imagined. On arrival in Jamaica, Ainsley believes he knows his father's family history as he has been told that his grandmother's family came to Jamaica as indentured labourers from India. Hoping to discover where exactly in India his great-grandparents came from, he is shocked to find himself heading down a very different path to the one imagined. Believing his grandfather's ancestry to be equally straightforward, Ainsley assumed that his great-grandfather was a slave before entering the colonial West India Regiment. In Barbados, however, he learns that apart from a distinguished career in the army fighting for the British Empire in the Sierra Leone Hut Tax War, little else is as he thought. Ainsley's journey leads him to wonder how, in the time of slavery, it was possible for one of his ancestors to accumulate enough wealth to buy seven houses. The answer is even more incredible than the question as he discovers that his great-great-grandfather was not a black slave at all.