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.
ON SEPTEMBER 19, 1787, James Wilkinson left New Orleans by ship bound for Charleston, South Carolina. Miró and Navarro reported that before sailing he had set up “one of the most complex ciphers to give us the news which this delicate subject may call forth.” Although often taken to be suspicious in itself, the use of a cipher was common in an era when letters were frequently opened by inquisitive postmasters, political opponents, and commercial competitors. What made Wilkinson’s ciphering exceptional was that he took to its use so readily. Whole swaths of his massive correspondence—a single communication might be thirty pages long— would eventually consist of numbers, symbols, or seemingly randomly selected letters. He expected congressional allies and friends such as Aaron Burr to decipher these, as well as his Spanish handlers.
Since he wrote in English, his reports not only had to be transcribed, but translated into Spanish. Replies went through the same process in reverse.
Miró never doubted that Wilkinson was worth the trouble. The Spanish cipher, using as its key an English- Spanish dictionary, was known within Spain’s colonial service as Number 13. Over time, and to preserve his anonymity, Miró and Navarro came to ascribe the name to Wilkinson himself, Agent 13. Eventually he insisted on being known by that pseudonym alone.
Miró and Navarro’s satisfaction in the outcome of that climactic summer was reflected in their recommendation to Madrid that as well as his commercial monopoly the American brigadier “be rewarded generously for his services if he succeeds in the first and principal object [Kentucky’s admission into the Spanish empire] or brings all his influence to bear in the accomplishment of the second [bringing American settlers to Louisiana].” They had exceeded their authority by allowing him to break the ban on American traders using the Mississippi, but promised that the value of imported goods would be capped at about thirty-five thousand dollars, and that the money would remain in New Orleans until Madrid had given its approval. From their point of view, it represented an important first step toward free trade. For Wilkinson, the move possessed far greater significance.
Up to this point, his betrayals had been small and personal. The agreement with Miró and Navarro had a different quality. It was the first tentative step toward leading a double life.
NOT UNTIL FEBRUARY 1788 did Wilkinson get home, and his delay in completing the last part of his journey after so long away almost broke Nancy’s nerves. “I have look’d for my Wilkinson this several Months with the utmost impatience, & now know not where he is,” she wrote her father. “The last letter I had from my Belov’d Wilkinson was dated at Richmond.
In that he assures me he will be Home by the 15th or 20th of Jan., & now it is the middle of Feb. I am sorry to express the feelings of my Heart so much— but indeed I am too wretched at the Long Absence of a dear Husband to feign a composure I do not feel at Present. I am almost distracted.”
Their son Joseph had been born in December 1785, her third child in three years. To add to the pressure of looking after three boys under the age of seven, just before her husband left for New Orleans, he had moved the family from the relative comfort of the frame house in Lexington that was also the store and taken them to land he owned in the wilderness of Frankfort. Although strategically placed near the center of the state, on the Kentucky River and at the edge of the bluegrass prairie, the isolated location had nothing to distinguish it from the rest of the empty, rolling landscape, except that in October 1786 the Virginia assembly had given Wilkinson permission to lay out a town on his property and operate a ferry across the river. To attract more inhabitants, he had a large, two- story house built in Frankfort and went to live there with his family.
While he was in New Orleans, however, Nancy was effectively marooned with her three small children, deprived of company and the comforts that were a necessity to her. Her eighty-one-year- old father sent her blankets and a barrel of sugar, whose sweetness she and the children adored, but she also needed new shoes for them and herself, scrubbing brushes, brooms, china cups, two hundred black sewing pins, and “a Pattern of a Black Sattin Cloak as I must make me one & wish to have it fashionable & let me know how they trim them [back in Philadelphia].” Most of all she yearned for contact with people who loved her, with her family—“It is impossible to say how much good perusing thy dear letter does me,” she ended one letter to her father—and with her absent husband.
Her emotional hunger matched his, and in the absence of Wilkinson’s letters to her, it must be presumed that this neediness was important to the warmth of their marriage. They were like each other, too, in the delight they took in clothes and luxuries, and in their lively talk and sociability. Usually their homes were filled with friends, and when Wilkinson had a regular income, the parties she gave were locally famous—and in the sparse society of the frontier that counted for much. But neither possessed the sort of practical skills to make the most of their demanding environment and between them were unable to cook, preserve, make do, add accounts, or save. Thus shortage of money to satisfy their wants constantly drove Wilkinson to ever more dubious ways of making it.
HIS GROWING POLITICAL STATUS had delayed his return to Frankfort. In his absence, the convention in Philadelphia had agreed on a constitution for a new federal government that the states now had to ratify. In Virginia, the outcome was close enough to make the votes of western settlers vital, and from Charleston, where he landed, through Philadelphia, Wilkinson’s views were sought and listened to by politicians at every level. Even Washington showed himself ready to set aside memories of Wilkinson’s behavior as clothier general and wrote expressing regret that “your business was so pressing as to deprive me of the pleasure of seeing you at this place.”
Back in Kentucky, his daring voyage and successful commercial arrangement with New Orleans marked him as a hero. Within weeks of his return, he had assembled a fleet of twenty- five large flatboats to take unprecedented quantities of tobacco, flour, and ham down the Mississippi. That summer, tobacco worth $2 a hundredweight in Kentucky sold for $9.50 in New Orleans; flour went for $7 a barrel, three times the price in Kentucky. Because the demand from New Orleans pushed up prices for those products across Kentucky, all growers benefited, small farmers and large- plantation owners alike.
The fleet was sent away under the direction of Wilkinson’s partner in the Lexington store, Isaac Dunn, and a young, high- spirited assistant, Philip Nolan. They traveled with letter
s of recommendation to Miró whose affectionate tone— Miró was “my dear friend” and “the friend of my bosom”— suggests that Wilkinson felt, or pretended to feel, the sort of affection that he had lavished on Gates. The salutation of a letter sent to Miró in February 1789 echoed the warmest of those he addressed to his general: “My much esteemed and honored friend, having written to you on the 12th instant, with all the formality and respect due to the Governor of Louisiana as the representative of his Sovereign, I will now address the man I love and the friend I can trust, without ceremony or reserve.”
With the seventeen-year-old Nolan, who worked as a bookkeeper in the Lexington store, the roles were reversed. Wilkinson was the patron, and the object of the younger man’s devotion. Indeed, Nolan must have reminded Wilkinson of himself at the same age—he commended the youth to Miró as “a child of my own raising”— although, as events were to prove, Nolan would turn out even wilder, more carefree, and less moral than his mentor.
That spring of 1788 New Orleans suffered the worst disaster in its history when fire swept across the city, destroying almost nine hundred buildings, and transforming three quarters of the city “into an arid and horrible desert,” as Miró’s official report put it. But a measure of his and Navarro’s efficiency was that they immediately provided public funds, organized building materials, and offered tax breaks to owners who rebuilt, so that by June when the Kentucky goods arrived, the vigorous rebirth of the city was under way. Navarro had retired in May, leaving the double burden of finance and government on Miró’s shoulders. Yet he seemed to thrive under the pressure, and Madrid rewarded him with promotion to the rank of brigadier “in testimony of the Royal satisfaction in his zeal.”
From New Orleans, Isaac Dunn sent word of their warm reception. The goods were not only admitted free of the 25 percent tax that other importers had to pay, they were stored in the royal warehouse, an added favor, although it came at a cost—“you cannot be at a loss to know where a participation of Profits is expected, & where it is due,” Dunn wrote discreetly, referring to Miró’s rake-off. But Wilkinson was accustomed to sharing profits with his partners. The only cloud over the enterprise concerned the quality of the tobacco: a quarter was deemed unsatisfactory, and another quarter was rotten enough to be destroyed. Nevertheless, his own share of the profits amounted to $9,830.50, a sum held for him by Daniel Clark, an Irish-born merchant in New Orleans.
Intoxicated by this return on his agreement with Miró, Wilkinson decided to back another trading scheme, heavily financed by Clark and approved by Miró, which was designed to tie Kentucky more closely into the New Orleans economy. In August 1788, with Dunn as a third investor, Wilkinson and Clark spent almost twenty thousand dollars on a cargo of luxury goods including sugar, linen, wine, and brass candlesticks to be exported back up the Mississippi to Kentucky. “It is exceedingly important,” Miró explained to Madrid, “that the Western people should see, before declaring themselves for a change of domination, that the true channel through which they are to be supplied with the objects of their wants, in exchange for their own productions, is the Mississippi.”
By the time he came to write his Memoirs, bitter experience had taught Wilkinson a lesson: “I am not by education, habit or disposition, fitted for a dealer or trader.” But in the summer of 1788, it seemed that whether as importer or exporter, he could not fail to make the “immense fortunes” that he had dreamed of when he set sail for New Orleans the year before.
9
CASH AND CONSPIRACY
THE EXPEDITION TO NEW ORLEANS cemented James Wilkinson’s reputation among Kentucky’s settlers. Its spectacular effect on prices was seen as confirmation of his political message that the settlers’ interests lay not on the Atlantic but westward with Spain. In June 1788, Miró advised Madrid that, such was Wilkinson’s influence among Kentucky’s swelling army of settlers, Miró had decided to accept the American’s demand for three thousand dollars in expenses rather than risk “the mischief that might arise from vexing him, and the impediments that the lack of Income would doubtless put in the way of his operations.”
The rapid progress of the conspiracy suggested it was a wise decision. On his return, Wilkinson had cautiously shared at least part of his plan for joining the Spanish empire with the “Kentucky notables” he trusted most. His first contact was with his lawyer, Harry Innes, by now impatient for independence from Virginia and willing to consider all options. His outlook was shared, though less enthusiastically, by judges Alexander Bullit and Caleb Wallace, and by other leading figures such as John Brown, the district’s representative in the Continental Congress, and a lawyer, Benjamin Sebastian. Only Innes and Bullit were trusted with the naked proposal that Kentucky should become part of the Spanish empire, and both recoiled. Wilkinson promptly toned down the plan to one of an alliance between Spain and the sovereign state of Kentucky. It was a small setback, but that summer 90 percent of the frontier votes went against ratifying the new, federal Constitution that had emerged from the convention. In Fayette County an overwhelming majority chose Wilkinson yet again to represent them at the next Danville convention, the sixth, to decide Kentucky’s future.
In July the latest convention again failed to resolve Kentucky’s future, but it was remarkable for the speeches of Innes, Wallace, and Sebastian demanding an immediate separation from Virginia without waiting for prior approval from Congress. “The consequences of depending on a body [the Virginia legislature] whose interests were opposed to ours were depicted in the most vivid colors,” Wilkinson reported to Miró, “and the strongest motives were set forth to justify the separation.” The convention agreed that at its next meeting, it would draw up a constitution and negotiate its independence from Virginia. Seen from New Orleans, the current of opinion was clearly flowing in the right direction.
In the summer of 1788, the current accelerated when Kentucky’s petition to become part of the United States was rejected by the Continental Congress on the grounds that no additional state should be admitted before the new federal government took office in 1789. The decision played directly into the conspirators’ hands. When the next convention, due in November, voted for independence from Virginia, it would also inevitably be voting for independence from the United States. To gauge Spain’s response, Kentucky’s representative in Congress, John Brown, made contact with Gardoqui, the Spanish ambassador, and was promised that concessions would be made to Kentucky for use of the Mississippi “if she will erect herself into an inde-pendent government. [But] they can never be yielded to her by Spain as long as she remains a member of the Union.”
In New Orleans, the normally cautious Miró 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 Miró, 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, Miró 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 Kentucké 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 Miró 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 Miró 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.
An Artist in Treason: The Extraordinary Double Life of General James Wilkinson Page 12