This dissertation is about how Jonathan Dickinson (1663-1722), a second-generation Anglo-Jamaican planter and early-Philadelphian merchant, made sense of the mercurial and uncertain Atlantic world around the turn of the eighteenth century. The following chapters examine Dickinson’s interactions with an extremely diverse group of European, Native American, and African peoples who collectively comprised a formative generation of colonial society in North America and the West Indies. The main purpose of this dissertation is to provide a counterpoint to the many tautologous, whiggish, and nationalistic interpretations of Anglo-Atlantic history that tend to deemphasise the obvious disconnections, disruptions, discord, and diversity apparent during the lateseventeenth and early-eighteenth centuries. This dissertation further contends that individuals, driven by self-preservation and influenced by local circumstances, dictated the direction and the pace of many inter-colonial, inter-imperial, and trans-Atlantic developments familiar to the late-eighteenth century Anglo-Atlantic world. In short, new exigencies outweighed custom, and self-preservation, rather than directives from metropolitan governments, guided Atlantic peoples’ actions. By extension of individual actions, the nascent British Atlantic Empire began to take shape.