I don't know about Barbados, but I can tell you that my ggrandfather on St. Vincent, who was from a "coloured" family although light enough to "pass," (as it would be put in the US) is described in a number of legal documents as a "Planter," and so are two of his associates, brothers, who I have pretty good reason to believe were also of mixed race and may have been his first cousins. I only have a photo of one of them (the associates, I mean), but he looks decidedly un-European. Among the three of them, they controlled a good portion of the agricultural land in SV betweem 1880 and 1900, more or less.

What was the position of "Headman"