United States–Caribbean relations over the period of the last thirty or forty years have rarely—if ever—been analysed in a thoroughly satisfying way. It is a strange omission in the international relations literature given the proximity of the United States to the Caribbean, and vice versa. But the fact is that most accounts of the relationship have fallen prey to a powerful, but ultimately misleading, mythology by which small, poor, weak, dependent entities in the Caribbean have either created trouble for, or alternatively been confronted by, the ‘colossus to the north’ that is the United States in whose ‘backyard’ they unfortunately have to reside. Virtually all analysts of the US–Caribbean relationship have thus drawn a picture marked at heart by the notion of an inherently unequal struggle between forces of a different order and scale. Within this broad metaphor the only major difference of interpretation has reflected the competing theories of power in the international system developed by the realist and structuralist schools.