Among this first wave of pioneers, James Wilkinson stood out. His exceptional war record, his political contacts in Philadelphia, his medical knowledge, and his outgoing personality, all counted in the turbulent, egalitarian society of Kentucky’s frontier. In staccato style, a fellow settler, Humphrey Marshall, noted the impact of Wilkinson’s physical presence, energy, and wit: “A person not quite tall enough to be perfectly elegant, compensated by symmetry and appearance of health and strength; a countenance open, mild, capacious, and beaming with intelligence; a gait firm, manly, and facile; manners bland, accommodating and popular; and address easy, polite and gracious, invited approach, gave access, assured attention, cordiality and ease. By these fair terms, he conciliated; by these he captivated.”
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.”