The introduction sets the scene for the book by presenting and explaining two concepts that are central to this study of the transimperial Greater Caribbean: spatial configurations and geopolitical imagination. The explanation of the first key term emphasizes the book’s approach to the role of mobility across political borders as central to the creation of lived geographies that result in the configuration of a regional space that is malleable, amorphously demarcated, and transimperial. In order to explain the innovation behind the study of this approach to regional configurations, the introduction discusses different ways in which historians have understood the geographical space commonly referred to as the Greater Caribbean. The second key term, geopolitical imagination, refers to the ways in which transimperial Greater Caribbean dwellers interpreted the events that characterized the present they inhabited, and how they used these interpretations to envision potential paths toward the future. The term is closely associated with widely used terms like “imagined communities,” “mental maps,” and “critical geopolitics.” The introduction also lays out the book’s contribution to Atlantic history by explaining how the approach of Creating Spaces, Envisioning Futures makes it possible to go beyond compartmentalized Atlantics that assume that empires function within self-sufficient spheres.