Enlightenment philosophers had long feared the effects of crisscrossing boundaries, both real and imagined. Such fears were based on what they considered a brutal ocean space frequented by protean shape-shifters with a dogma of ruthless exploitation and profit. This intellectual study outlines the formation and fragmentation of a fluctuating worldview as experienced through the circum-Atlantic life and travels of merchant, slaveowner, and slave trader Zephaniah Kingsley during the Era of Revolution. It argues that the process began from experiencing the costs of loyalty to the idea of the British Crown and was tempered by the pervasiveness of violence, mobility, anxiety, and adaptation found in the booming Atlantic markets of the Caribbean during the Haitian Revolution. Tracing Kingsley’s manipulations of identity and race through his peripatetic journey serves to go beyond the infinite masks of his self-invention and exposes the deeply imbedded transatlantic dimensions of power.