When Josiah Blakeley, consul of the United States at Santiago de Cuba, wrote these lines to Secretary of State James Madison on November 1, 1801 he had recently been jailed by administrators on that island. This remarkable situation notwithstanding, his sentiments still neatly express the paradox of trade between the United States and Spanish Caribbean ports. The expanding hinterlands of New York, Philadelphia and Baltimore furnished North American merchants with ever increasing, exportable food supplies and led to fierce competition for new markets at the end of the eighteenth century. At the same time, Spain\u27s American colonies remained chronically, often desperately, short of food-stuffs. Imperial bureaucrats at many levels consistently recognized this problem, yet they imposed numerous trade restrictions. Even more than the dizzying pace of war and peace itself after 1793, these restrictions made North American commerce with the Spanish Caribbean volatile, risky and undesirable for many. This essay focuses not upon those who were deterred from the trade, but rather upon a small network of North Americans who, despite the uncertainties, chose to operate within these markets. First, the salient characteristics of their businesses are outlined. Then, it is argued that their behavior departed from the models postulated for American merchants that have been developed by students of the period. As opposed to luck or \u27imaginative innovation\u27 or aggressive individualism, the key factor emphasized here is cultural flexibility.5 Moreover, the research is drawn from archives, both foreign and domestic, that are not often consulted by Anglo-Americanists. At the very least, this strategy allows a more correct identification of the individuals involved in trade with the Spanish Empire
