Filson’s main text, however, amounted to an advertisement for Kentucky real estate. He described a fabulous land where a hundred bushels of corn per acre could be grown without the need for irrigation or fertilizer, along with sugar, coffee, cherries, and cucumbers, where the existing settlers were “polite, humane, hospitable and complaisant,” where scores more arrived every day so that “the country will be exceedingly populous in a short time,” and where property could be bought simply and safely because Kentucké belonged to the state of Virginia and was “governed by her wholesome laws, which are virtuously executed, and with excellent decorum.”
Yet the failure of Virginia’s government to operate either virtuously or decorously was precisely what infuriated Kentucky settlers. The most serious failing was the absence of protection against Indian attacks, principally by the Shawnees, who claimed hunting rights and saw their game increasingly frightened off by European settlers. Located two or three weeks away across the Allegheny Mountains, the Virginia legislature could not call out the militia in time, and left to their own defenses, more than one third of the two hundred pioneers round Lexington had been killed in a single Shawnee attack in 1782.
Less dangerous, but more toxic to the hopes of new settlers, was the confusion over land titles. To convert the wilderness into rapturous property, the land had to be surveyed, then the claim had to be registered and title to the property patented, both in Richmond. Even without counterclaims, a minimum of ten months was required. And Virginia’s decision to mortgage much of Kentucky to fund its wartime expenditure made counterclaims inevitable.
The state printed paper money with a face value of more than sixty million dollars during the war, much of it backed by land in the west. By 1783, wealthy speculators in the east owned huge quantities of treasury bills and certificates, bought cheaply when their value dropped to one tenth of a cent in the dollar, that entitled them to ownership of up to one third of all Kentucky. Poorer settlers who came west to claim their land in person discovered that they were debarred from the best ground, or that farms they were working really belonged to a stranger far away in Richmond or Philadelphia. In 1785, the traveler Michael Austin passed more than seven hundred pioneers on the Wilderness Road heading for Filson’s dream country. “And when arrivd at this Heaven in idea,” he warned, “what do they find? a goodly land I will allow, but to them forbidden Land.”
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.