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The memorial presented a program for their mutual advantage. Its first part concerned the political future of the western settlers. Wilkinson had come to New Orleans, he said, at the request of “the notables of Kentucky” to discover whether Spain might be interested in opening negotiations “to admit us under its protection as vassals.”

The key to the loyalty of the Kentuckians, he explained, was access to the Mississippi, “the object on which all their hopes of temporal happiness rest, and without which misery and wretchedness is their certain portion.” To gain it, their present inclination was to ally themselves to Spain, but if that failed, they would turn to Britain for help. To decide the issue, Spain needed to act immediately. Wilkinson recommended that it should begin by “peremptorily and absolutely [refusing] to the Congress the Navigation of the Mississippi” in order to force the settlers to look to “the power which secures them this most precious privilege.”

This was the heart of what became known as the Spanish Conspiracy: to induce the Kentuckians, by offering the reward of free trade on the Mississippi, to leave the Union and become part of the Spanish empire. As its instigator, Wilkinson promised to employ “all my faculties to compass this desireable event.”

Although his recommended tactic of shutting the river to American traffic was the reverse of the policy that made him popular in Kentucky, he insisted that “a man of great popularity and political talents will be able to alienate the Western Americans from the United States, destroy the insidious designs of Great Britain and throw [the Kentuckians] into the arms of Spain.” Such a person would need to be rewarded. It would be advisable, therefore, “to offer indulgence to men of real influence” by allowing them to ship goods to New Orleans free of charge.

Independently of this policy, he also recommended that the Spaniards construct a strong defensive post near the settlement of New Madrid, just below the junction of the Ohio River with the Mississippi. This was needed because in any negotiations between Spain and the United States “the more respectable and independent the military stength of the former, the greater will be the concessions she will receive from the latter.” Once the post was constructed, immigrants should be encouraged to settle below the fort with the inducements of free land, religious toleration, and free trade on the Mississippi. Americans would flood in and “this Province would then rise into immediate Wealth, Strength and National Importance.”

In his Memoirs Wilkinson denied that he had done anything more than offer empty promises in return for the commercial advantage of importing tobacco and other products to New Orleans. “The idea of alienating Kentucky from the United States, while a prospect of national protection remained, would have been as absurd as the idea of reducing them to the vassallage of Spain,” he declared, knowing that he had advocated both.

A few years later he certainly urged an associate, Hugh McIlvain, to follow his example. “When you get to Natchez, put on your best bib and tucker,” he advised. Smartly attired, McIlvain should flatter Miró, take an oath of allegiance, and “to his enquires respecting Kentucky, say nothing that is not flattering and favourable to Luisiana.” The purpose was simply to get permission to sell tobacco in New Orleans.

Yet if his “Memorial” was designed to secure valuable trading rights, it could achieve that end only by being a serious proposition. Both Miró and Navarro were realistic enough to understand that Wilkinson was less committed than he pretended, but they were also shrewd enough to guess that he could be persuaded to perform more than he intended. To secure his loyalty, they were prepared to offer not just financial inducements, but their esteem and respect. To someone as economically careless and emotionally hungry as Wilkinson, that exchange would come to seem like an irresistible bargain.

The next day, August 22, he signed a formal document “transferring my allegiance from the United States to his Catholic Majesty.” For McIlvain and many other Americans who later made similar declarations when they sought Spanish trading privileges, this amounted to no more than a formula. But Wilkinson went on to defend what he had done in words clearly intended to carry weight with the two men he wanted to impress.

Echoing Washington’s own dictum, he asserted, “[Self]-interest regulates the passions of Nations, as also those of individuals, and he who attributes a different motive to human affairs deceives himself or seeks to deceive others: although I sustain this great truth, I will not, however, deny that every man owes something to the land of his birth.” To explain how his interests had come to diverge from those of his country, he reverted to a familiar theme— blaming his behavior on the failings of someone, or in this case some country, he had trusted.

“Born and educated in America, I embraced its cause in the last revolution, and remained throughout faithful to its interest, until its triumph over its enemies,” he declared. “This occurrence has now . . . left me at liberty, having fought for her happiness, to seek my own. [But] circumstances and the policies of the United States having made it impossible for me to obtain this desired end under its Government, I am resolved to seek it in Spain.”

Defiantly, he declared that no one could accuse him of having “broken any of the laws of nature or of nations, nor of honor and conscience” in changing his allegiance, but the conclusion of his “Memorial” made his unease explicit: “Gentlemen, I have committed secrets of an important nature, such as would, were they divulged, destroy my Fame and Fortune forever.” Should their plans not work out, he relied on Miró and Navarro “to bury these communications in eternal oblivion.”

SEEN ACROSS MORE THAN TWO CENTURIES, the Spanish Conspiracy might appear doomed to failure, but Americans living in the years immediately after the Revolution saw it in a different context. To them the ramshackle constitution created by the Articles of Confederation seemed more likely to destroy the Union than hold it together. A bankrupt Congress, dependent on revenue from the states, could do nothing to prevent the different economic interests within the United States from pulling it apart.

Democratic, commercially minded New Englanders had little in common with aristocratic, rural southerners. Fiscally conservative southerners were infuriated by the north’s readiness to print paper money to pay its debts, and shocked by the lawlessness that erupted into tax revolts such as Shays’s Rebellion in 1786. The decision of northern states to follow Pennsylvania and Massachusetts in abolishing slavery alienated southern plantation owners, who felt their human property under threat. The catalyst for these divisions came in November 1786, when Henry Knox assured his former commander in chief that up to fifteen thousand New Englanders were ready to rebel rather than pay more tax. A shaken Washington stared into the abyss. The United States, he told Knox, was “fulfilling the prediction of our transatlantic foe! ‘leave them to themselves, and their government will soon dissolve.’ ”

Their fear that the Union really would fall apart was what drove James Madison and George Washington to push for a new constitution and the creation of a stronger federal government. It was no coincidence that James Wilkinson’s negotiations with Miró and Navarro in the summer of 1787 coincided with the proceedings of the Constitutional Convention in Philadelphia. One set of negotiations was aimed at partition, the other at union, but each arose from the same divergent tendencies within the United States.

Until a new central government showed it could protect the western settlers’ interests, Wilkinson’s proposals would continue to provide the largely hidden agenda of Kentucky politics. They would also become the last, best hope for the survival of the Spanish empire in North America.