One of the many minor mysteries surrounding the history of sugar production in the colonial greater Caribbean concerns differences in the organization of production between the English islands and Brazil.1 In Brazil, production was dispersed, as much of the cane was grown by small farmers (lavradores de cana), some of them tenants, some independent landowners who took their crop to their landlord's mill or to some other big planter's mill for processing. On the islands, by contrast, production was centralized, as most of the cane was tended by slaves owned by a big planter and processed at the planter's own mill. Given the high productivity of gang labour, there would seem to be substantial advantages to the centralized system that prevailed on the islands. It is therefore something of a puzzle why the centralized system did not prevail throughout the region. This chapter, through a focus on Barbados and Brazil in the seventeenth century, attempts a solution to that puzzle. While it might at first seem odd to compare a small island like Barbados to a colony as large as Brazil, several considerations suggest that the comparison is in fact well grounded. In the middle seventeenth century, the period focused on here, Barbados was Brazil's most serious competitor as a sugar producer.