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

by Andro Linklater

  This pleasing impression was reinforced by the evidence of his wealth, or at least of wealthy backers. Despite having limited funds at his disposal, within three months Wilkinson had bought 12,550 acres on the Kentucky River and filed claims for another 18,000 acres at the Falls of the Ohio, the future Louisville, and farther east on the Licking River where the land was cheaper. Following old frontier advice that “the best method of getting first- rate lands . . . is by way of goods,” he set up a store in Lexington, a strategic point at the end of a good trail from Virginia. The settlement amounted to no more than thirty log cabins and a stockade on either side of a dusty track, but from here new arrivals might move northwest to the Ohio or southwest into the grassy “wilderness.”

  The money for buying land came from wealthy friends in Philadelphia, such as Dr. Hugh Shiell, a Scots land speculator, and his brothers- in-law, James Hutchinson and Clement Biddle, while the Lexington store was set up with two partners he had known from his days on Horatio Gates’s staff, Isaac Dunn and James Armstrong. Even the goods it sold, lengths of calico, corduroy, chintz, and Marseilles lace suitable for petticoats, as well as shoes, beads, “trinkets and gewgaws,” were supplied on easy terms courtesy of another friend, John Moylan, whose business, Moylan, Barclay & Company, was one of the largest in Philadelphia.

  Within Kentucky itself, the warmth of Wilkinson’s personality quickly enabled him to build up a network of useful friends. At its heart was his lawyer, Harry Innes, the newly appointed attorney general for Kentucky district, who handled all Wilkinson’s land deals and increasingly complex financial arrangements. Another was Humphrey Marshall, who, seduced by the newcomer’s winning personality, promised to join forces with Wilkinson in the search for suitable land, a pledge that in time developed into lawsuits and a rancorous hatred.

  In his early days on the frontier, however, Wilkinson’s charm was literally as bankable as cash. Half a century later, William Leavy, whose father arrived in Lexington in 1785, could still remember Wilkinson’s “wonderful address” in dealing with awkward financial affairs. “A friend living in the neighborhood of Lexington had loaned Wilkinson money,” Leavy recorded, “which, on making a special call at his house to ask its return—he was so graciously received by him— having him to dine, &c.— that in place of urging its return he was before he left the house induced to increase the loan.”

  Frontier life also required a rugged determination that Philadelphia society rarely demanded. In Wilkinson’s first winter, the cold was so intense that the Ohio River became blocked by slabs of ice as early as November, trapping a boatload of goods destined for the Lexington store, and the snow lay so deep it took the train of pack horses sent to rescue the cargo seven days to reach the river. Wilkinson boasted that he spent so many days on horseback exploring the wilderness that he knew it “better than any Christian in America.” He used to lead a mule loaded with goods to sell, and bacon and biscuit for his food to save the expense of “damn’d Tavern Keepers,” but wherever he went, his eyes were always open for good land to buy, both for himself and for his eastern backers. In July 1784, he signed a contract with John Lewis, a Philadelphia financier, to find and acquire eleven thousand acres, in return for which Lewis promised to give Wilkinson half of all the land he located.

  The return on real estate was slow, however, and the store paid the bills. In his first year of business, bags of salt, essential for curing pork and preserving other food, were added to the goods for sale, and in July Wilkinson set up a partnership with Lewis to trade with Shawnee townships, giving cloth in exchange for beaver pelts and other furs. Probably the Lexington store also sold seeds and medicines, because writing to another military acquaintance, General Charles Scott, Wilkinson lamented the difficulty of getting vegetables suitable for the Atlantic coast to grow in Kentucky. “Be sure you bring a double stock of great variety,” he advised Scott, “and try to make out more with Turnips and Potatoes— get a snug little assortment of medicine; don’t forget Blistering Plaister, a plenty of Salts, Tart- Bark [for malaria], Laudinum [for pain relief].” In 1786, Wilkinson also built a tobacco warehouse, and in Virginia’s tobacco economy, this was equivalent to setting up a bank, because the receipts he issued at three dollars per hundredweight of leaf could be exchanged as legal tender. Within three years, he had become a leading figure in Kentucky’s growing community.

  His letters to friends in the east made no mention of political difficulties and became prolonged invitations to come and settle. “Our country is now a continued Flower Bed,” he told Charles Scott in 1785, “and the whole aire breathes the richest fragrance . . . The Indians are peaceable, and [the price of] corn and Bacon is on the fall.”

  In September 1784, Nancy and the two boys succumbed to his entreaties and left Philadelphia for life on the frontier. Unlike her husband, Nancy hated the harshness of the wilderness. Even three years later, she still bitterly missed her family and the conversation and comforts of city life. “It is impossible for me to describe the torture my mind endures,” she wrote to her father, “not [being] blessed with the Sight of a relation this ten months, & Surrounded by People that has been brought up so differently from myself, that when Sick & Low spirited, there Company only disgusts— O what would I not give to be blessed with a sensible agreeable woman for a Neighbour that had been brought up tenderly as I have myself.”

  Quick- witted, gentle, and funny, she had the qualities of a city girl rather than the hard endurance needed by a frontier wife. The affectionate messages to her that Wilkinson’s friends always included in their letters show how much she was liked, and according to rumor, Lexington’s inhabitants much preferred her to her self- promoting husband. But for Nancy, Wilkinson was the only thing that made Kentucky bearable. With months of her arrival in Kentucky she was pregnant once more, and when he was away, she confessed to her father, “I feel so Stupid I Can scarce hear my Children when they speak to me; my Jimmys [sic] Presence would soon make me well.” However, soon it was not only business and land- hunting that drew him from her side. Wilkinson had become involved in Kentucky politics.

  ALTHOUGH THE MYTH of frontier life promised an escape from government and the constraints of the law, the reality made it impossible to avoid either. The first guide to Kentucky life, John Filson’s The Discovery, Settlement and Present State of Kentucké, published in 1784, illustrated why. The myth was catered to in the appendix. This contained the story of Daniel Boone, the archetype of the frontier hero, who enjoyed danger and solitude, and who climbed to “the summit of a commanding ridge” simply for the pleasure of viewing “the ample plains, the beauteous tracts below [stretching to] the famous river Ohio that rolled in silent dignity, marking the western boundary of Kentucke with inconceivable grandeur.” Speaking the language of the romantics, Boone concluded, “No populous city, with all the varieties of commerce and stately structures, could afford so much pleasure to my mind, as the beauties of nature I found here.”

  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 mili
tia 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.

  “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.”

  Even Kentucky’s attorney general, Harry Innes, was convinced that “this country will in a few years Revolt from the Union and endeavor to erect an Independent Government.” His belief was loudly endorsed by his client James Wilkinson. But before the convention could discuss the matter, a new Indian attack across the Ohio called away so many delegates to join in the defense of their homes that proceedings had to be abandoned, leaving the great question unanswered for another year.