An Artist in Treason: The Extraordinary Double Life of General James Wilkinson

In New Orleans, the normally cautious Miro looked forward to Kentucky’s November convention and confessed to Antonio Valdes, the minister for the Indies and his political master in Madrid, “This affair progresses more rapidly than I had anticipated.” In his frustration Brown had told a friend, who passed the news on to Miro, that he intended “to call for a general assembly of his fellow citizens, in order to proceed immediately to declare themselves independent, and to propose to Spain the opening of a commercial intercourse with reciprocal advantages.” In the spring, Miro predicted, “I shall have to receive a delegation [from Kentucky] appointed in due form,” and asked Valdes how he should respond.

A small but significant setback occurred before the convention opened. Brown mentioned Gardoqui’s offer to George Muter, who was in favor of splitting from Virginia but not from the Union. Muter immediately leaked the letter to the Kentucke Gazette. It crystallized opposition among the “country party,” composed of large-plantation owners whose property titles, often acquired with Virginia’s paper money, might be questioned should Kentucky become a sovereign power. Undeterred, Wilkinson delivered a speech on the opening day that outlined the steps needed to achieve the goal that all Kentuckians wanted, the freedom to carry their goods down the Mississippi. “The way to obtain it,” he argued, “has been indicated in the former convention, and every gentleman present will connect it with a declaration of independence, the formation of a [Kentucky] constitution and the organization of a new State, which may safely be left to find its own way into the Union on terms advantageous to its own interests.”

According to Edward Butler, who wrote his History of Kentucky in 1834 while the convention was still within living memory, Wilkinson dominated the proceedings: “This gifted man drew all eyes upon him and was looked up to as a leader and a chief.” But opposition to the idea of independence was already growing from the country party, led by Muter and Humphrey Marshall. Looking for allies, Wilkinson turned to his fellow conspirator John Brown, expecting him to cite Gardoqui’s offer as evidence of the advantages of independence. But Brown had been worked on by Muter. At the crucial moment he lost his nerve and called instead for unanimity in whatever they decided. “He is a young man of respectable talents, but timid, without political experience, and with very little knowledge of the world,” Wilkinson reported in disappointment to New Orleans. “Nevertheless, he firmly perseveres in his adherence to our interests.”

The next day Wilkinson adopted a bold strategy. He read a long paper to delegates modeled closely on his New Orleans memorial, but crucially omitting any reference to becoming “vassals” of his Catholic Majesty. No vote was taken on its proposals for independence and a Spanish alliance, but the convention voted to thank him for his address, while it tabled Brown’s motion for joining the Union. Delegates might sympathize with Wilkinson’s aims, but for most the double leap that independence required— defiance of Virginia and rejection of the United States— was too much. The only action they could agree on was to call for an eighth convention after the new federal government was elected.

Politically the November convention was a failure, but in the slow development of Wilkinson’s double personality it became an important milestone. In February 1789, he sent Miro a long account of his performance at Danville that was almost entirely deceptive. Despite the opposition of the country party, he claimed “our cause has acquired considerable force.” Relying on the lack of good communication between Kentucky and New Orleans, he assured Miro that “in order to elicit an unequivocal proof of the opinion of that assembly, I submitted to its examination my memorial, and the joint answer of yourself and Navarro.” To confirm that he was telling the truth, he enclosed newspaper cuttings with reports of his speech, together with the convention’s expression of gratitude and its rejection of Brown’s resolution.

Sending the letter and the newspapers on to Madrid, Miro added his own balanced view of what had happened. “You will find an account of the bold act which General Wilkinson has ventured upon, in presenting his first memorial in a public convention,” he told Valdes. “In so doing, he has so completely bound himself [to us], that, should he not be able to obtain the separation of Kentucky from the United States, it has become impossible for him to live in it, unless he has suppressed, which is possible, certain passages which might injure him.”

That delicate cocktail of hope and distrust became the hallmark of Wilkinson and Miro’s relationship. Each liked, exploited, and was compelled by political and financial necessity to forgive the other. “I am aware that it may be possible that his intention is to enrich himself at our expense, by inflating us with hopes and promises which he knows to be vain,” Miro acknowledged to Valdes. “Nevertheless, I have determined to humor him.”

On his side, Wilkinson always assumed that his efforts to deceive were no more than those practiced on him by the governor and Navarro. Or as he put it in his autobiography, “It is but reasonable to presume, that they had duties and obligations to consult as well as myself; and . . . it was fair that they should play back upon me my own game, to the best advantage.” In fact, apart from taking a cut of Wilkinson’s profits, Miro handled Wilkinson with remarkable integrity, noting his failures and weaknesses, but never cheating or blackmailing him. From this uneven base grew an astonishingly firm friendship, the most enduring of Wilkinson’s oddly dependent relationships, and one that seamlessly evolved into that between spy and handler.

UNDER THE LAYERS OF DECEPTION that Wilkinson was beginning to practice with growing ease lay unavoidable truths. The first was his financial extravagance. The second was the realization that his one hope of economic rescue lay in New Orleans. The third was that others wanted to take his place in Spanish affections. All these were thrown into sharp focus by the response of the royal council in Madrid to his memorial.

No direct comment was sent to Miro, but in May 1788, Spain’s chief minister, Jose, Count of Floridablanca, had instructed the Spanish minister in Philadelphia, Diego de Gardoqui, of a change in official strategy. The Mississippi would remain closed, but Spain should boost the population of its North American colonies by trying “to attract to our side the inhabitants of the Ohio and Mississippi.” In response, Gardoqui became an enthusiast for inducing Americans to migrate to Louisiana and Natchez by offering them free land, access to the river, and religious toleration.

All at once Wilkinson’s privileged position was threatened by the readiness of other prominent Americans to take advantage of Gardoqui’s offer. George Rogers Clark, the hero of the capture of Vincennes from the British, asked for permission to settle in Louisiana, as did Friedrich von Steuben and Daniel Boone, while John Sevier, victor of Kings Mountain in the south and founder of the short- lived Franklin colony, assured Gardoqui that the settlers in eastern Tennessee were “unanimous in their vehement desire to form an alliance and treaty of commerce with Spain, and put themselves under her protection.” In December 1788, Wilkinson’s own partner Isaac Dunn hurried into Frankfort with news that Gardoqui had approved a proposal by Colonel George Morgan to settle one hundred thousand people on several million acres in Louisiana. His project had already reached the stage of receiving permission to create a town on the Mississippi that its owner called New Madrid.

As a result, every word of Wilkinson’s letter to Miro in February 1789—and the lies about the convention made up only a small part—was designed to demonstrate his unique usefulness and loyalty to Spain’s interests. Bundled up with his writing was a letter from his old commanding officer, General Arthur St. Clair. It had been sent to Dunn and described St. Clair’s distress at hearing that “our friend Wilkinson” was a leader of the Kentucky secessionists, whose goal “would completely ruin this country.” Unaware that Dunn was part of the conspiracy, St. Clair pleaded, “Should there be any foundation for these reports, for God’s sake, make use of your influence to detach Wilkinson from that party.” This was proof, Wilkinson confided to Miro, “that the part which I play in our great enterprise, and the dangers to which I am exposed for the service of his Catholic Majesty, are [publicly] known.”

As though this were not enough, Wilkinson also told the Spanish governor that in November 1788 he had been contacted by John Connolly, a British spy sent to investigate the loyalties of western settlers by Lord Dorchester, governor of Canada. Connolly’s cover was the pretense of trying to recover Kentucky properties confiscated during the war, but it was blown as soon as he entered the newly established Northwest Territory beyond the Ohio River. “My Information is, that he is sent to tamper with the People of Kentuckey and induce them to throw themselves into the Arms of Great Britain,” St. Clair, the territorial governor, informed John Jay in Philadelphia, “. . . [and] if that cannot be brought about, to stimulate them to Hostilities against the Spaniards, and at [any] rate to detach them from the united States.”

Connolly had visited Wilkinson expecting him to be sympathetic and promised British money, ammunition, and ships to help the Kentuckians “open the navigation of the Mississippi.” But by Wilkinson’s account, instead of welcoming an insurrection that was both anti- Spanish and anti-American, he made Connolly the victim of an audacious sting. “I employed a hunter, who feigned attempting his life,” Wilkinson boasted to Miro. “As I hold the commission of a Civil Judge, it was, of course, to be my duty to protect him against the pretended murderer, whom I caused to be arrested and held in custody. I availed myself of this circumstance to communicate to Connelly