By the latter quarter of the eighteenth century, as the movement against the slave trade increased in Britain, Creoles, those of British ancestry born in the West Indies, were increasingly criticized for their involvement in slavery. Simon Taylor, a Jamaican-born planter of Scottish ancestry who lived most of his life in the colony, attempted to negotiate competing and often contradictory sensibilities and subject positions as both British and Creole. One of the central challenges to Taylor’s negotiation of identity was his long-term relationship with Grace Donne, a free mixed-race woman of colour. An examination of their relationship highlights the ways binary discourses and exclusionary practices devised to create and reinforce rigid racial boundaries were regularly crossed and blurred, even by an individual like Simon Taylor, a person well placed to benefit from the policing and maintenance of those boundaries.