Andro Linklater - An Artist in Treason - The Extraordinary Double Life of General James Wilkinson

Caught in the morass of competing claims and dogged by fraud and widespread corruption, Kentucky’s property market would become so notorious for the uncertainty of its land titles that within a generation one expert predicted accurately, “The titles in Kentucky w[ill] be Disputed for a Century to Come yet, when it’s an old Settled Country.” For many Kentuckians, the only possible solution was to cut themselves free from Virginia. Beginning in 1784, a series of settlers’ conventions took place in the eastern town of Danville to consider proposals for separation from Virginia.

It was always likely that Wilkinson’s volatile temperament, so quick to resent direction from above, would drive him to join the anti-Virginian movement. But he had other more pressing motives. He had made large purchases of land, then used some as collateral on loans, usually from his partners, and Wilkinson’s tendency to extravagance meant that most of his partnerships ended in quarrels and litigation. He made the problem worse by running up lines of credit with friends to raise ready cash for urgent purchases. “I find I shall be under the necessity of employing about £40 of your cash to discharge sundry engagements incurred on Acct. of the old cargo,” he wrote his associate Hugh Shiell late in 1784, “for which I will give you a bill at 30 Days on Col. [Clement] Biddle.” Either because of this transaction or another soon afterward, Shiell broke off their association. He was replaced by Peyton Short, son- in- law of the wealthy John Cleves Symmes, who had bribed his way to ownership of more than a million acres of government land north of the Ohio River. That partnership also eventually broke down. In each case, land had to be sold hastily to pay the debt before Wilkinson had time to benefit from the rise in its value.

As he admitted in his Memoirs , he was “far from affluent [and] my expectations were damped by the obstructions which the Spaniards opposed to the free navigation of the Mississippi.” In colonial times and for most of the war, the river had been under the loose control of the British, who had allowed settlers to ship their tobacco, flour, and whiskey down the river to New Orleans. But in a lightning campaign in 1781, Spanish forces had taken control of the Gulf Coast and the river, and since 1783 the Mississippi had been closed to American traders. Nothing would do more to increase the prosperity of Kentucky, and of Wilkinson, than opening the Mississippi to navigation by American vessels.

Wilkinson missed the first two Danville conventions, but was elected to the third in August 1785, where a formal petition calling for Kentucky’s independence was sent to Richmond. By then his social influence equaled his personal ambition, and his fellow delegates appointed him to write “in the plain, manly and unadorned language of independence,” as he described his flowery style, the actual petition to the Virginia assembly that called for legislation “declaring and acknowledging the independence of the District of Kentucky.” In the excitement, the resolution passed by the convention merely called for Kentucky’s independence but said nothing of seeking admission to the Union.

This was not entirely a mistake. Kentucky’s assertive settlers had no particular loyalty to the United States. As Washington himself admitted to Richard Henry Lee in August 1785, “There is nothing which binds one country or one State to another but interest. Without this cement the Western inhabitants can have no predilection for us.” One powerful interest did tie Kentucky to the United States, however: the need for help in opening the Mississippi River so that settlers could ship their produce to the great port of New Orleans. Because Spanish galleys and forts dominated the river as far north as the mouth of the Ohio, Kentucky’s farmers wanted the American government to bring diplomatic pressure to bear in Madrid. If they did not get what they wanted, Wilkinson assured his brother- in-law James Hutchinson that year, “The People of Kentucky alone, unaided by Congress . . . could dislodge every Garrison the Spaniards have on or in the Neighborhood of the Mississippi.” The Danville delegates certainly knew of Wilkinson’s outlook, and suspicious of a Congress influenced by New England representatives with little interest in opening up the Mississippi, most welcomed his call for Kentucky to take unilateral action.

In January 1786 Virginia’s legislature responded cooperatively by passing an enabling act that allowed Kentucky to separate on three conditions—a convention formally voted for it, a suitable constitution was adopted, and Congress voted for the state’s admission to the Union. The convention that met at Danville in September 1786 was intended to be the first step along this path. Wilkinson, representing Fayette County, arrived there in his guise as landowner, storekeeper, tobacco banker, and leading citizen. Continuing his theme from the previous convention, he argued for total independence from both Virginia and the United States. He made his case in a speech that marked his arrival as one of the dominant figures in Kentucky politics, a place he continued to occupy for the next fifteen years.

“I pleased myself,” he boasted to James Hutchinson after his triumph, “&, what was more consequential, every Body else, except my dead opponents— these I with great facility turned into subjects of ridicule and derision.” He had planned to speak for no more than ninety minutes but found to his surprise that he had been on his feet for three and a half hours. Life in Kentucky, he concluded, had altered him. “I have experienced a great change since I held a seat in the Pennsylvania Assembly,” he confided to Hutchinson. “I find myself much more easy, prompt, & eloquent in a public debate, than I ever was in private conversation, under the greatest flow of spirits.”

Yet it was not so much Wilkinson’s eloquence as the behavior of Congress that drove the movement for Kentucky’s total independence. Throughout the critical year of 1786, the United States, represented by the secretary for foreign affairs, John Jay, had been negotiating with Don Diego de Gardoqui, the Spanish minister in Philadelphia, to find a way of continuing the alliance that had begun during the war with Britain. The diplomats agreed that difficulties over the frontier they shared along the Mississippi had to be balanced against the mutual advantages of increasing trade. Scenting mischief, Wilkinson had warned as early as April 1786 that Jay was secretly prepared to sacrifice Kentucky’s need to have access to the Mississippi. He swore to make it his mission to alert every settler in the district: “They shall be Informed or I will wear out all the Stirrups at every Station.”

Despite the myth, the frontier grew around communities rather than individuals. Public buildings were invariably constructed, a stockade, a church, a courthouse, a tavern, where people met to share past experiences and future forebodings. At these places and at social events such as turkey shoots and militia musters, a stranger with the gift of the gab could be sure that he would have an audience, and that his news and views would noisily be chewed over by outspoken frontier folk.

During 1786, his third year in the west, Wilkinson made his name widely known. When the convention met in Danville, independence for Kentucky was no longer an extreme view but close to a majority opinion. It was generally known that Jay had concluded an agreement with Gardoqui accepting the closure of the Mississippi in exchange for allowing shippers and businessmen on the Atlantic coast access to Spanish ports. In Congress, a bare majority of the states voted to accept Jay’s agreement. Since nine of the thirteen were required to approve a treaty, Jay’s agreement failed to become law, but, according to James Monroe, the barefaced betrayal of Kentucky’s interests was deliberate. The northern states intended “to separate those people, I mean all those westward of mountains, from the federal government, perhaps throw them into the hands eventually of a foreign power.”