Three weeks later, Miró sent a message to Valdes urging him to put this talent for dissembling on a professional basis: “I am of opinion that said brigadier-general ought to be retained in the service of his Majesty, with an annual pension of two thousand dollars, because the inhabitants of Kentucky, and of the other establishments on the Ohio, will not be able to undertake anything against this province, without his communicating it to us, and without his making at the same time all possible efforts to dissuade them from any bad designs against us, as he has already done repeatedly.”
Don Esteban Miró had been appointed governor of Louisiana and West Florida in 1782, immediately after the Gulf Coast and the Mississippi River had been seized from the British. When he arrived, the colonies were racked by racial tensions between French and Spanish, the economy was moribund, and the land empty enough to be called “a desert.” By the time he was recalled to Spain at the end of 1791, Louisiana was calm, growing in prosperity, and its population had more than doubled to about fifty thousand.
Yet of all the advantages he bequeathed, no single one was more useful than his success in recruiting James Wilkinson as a spy. As a civilian, his friend might only be able to pass on information, but before the year was out, the onetime brigadier general would be on the way back to his old profession.
IN BUSINESS AS IN WAR, a chief executive needs luck. Wilkinson was both careless and unlucky. The shipwreck and suicide that ate up the profits of 1789 were followed in 1790 by the loss of two thirds of his cargo. Since speed was essential to get the best prices in New Orleans, the adventurous Philip Nolan had volunteered to take Wilkinson’s flatboats boats down the snow- swollen Kentucky River in spring. With navigation marks obscured, he ran three of them onto sandbanks, where the receding water left them stranded through much of the summer. A fourth sprang a leak in the turbulent current, ruining part of its cargo.
Growing competition had made the gamble necessary. Wilkinson’s pioneering voyages had shown other settlers the profits that could be made, even paying 15 percent duty. Those living closer to the Ohio or on the Mississippi itself were able to get to market quicker than he, and many found that bribery and forged papers allowed them to escape the duty.
“Let me conjure you to be rigid in exacting the duty [and] every other charge,” Wilkinson begged Miró in February 1790. And just before Nolan left with the boats, Wilkinson wrote again with greater desperation, “For God’s sake cut off the commercial intercourse with this country [Kentucky], it utterly destroys all our plans & views, & if not immediately checked may eventually ruin Louisiana.”
That year Wilkinson secured a new partner, Peyton Short, son- in-law of the wealthy land speculator John Cleves Symmes. But even with his help, Wilkinson had had to borrow money to assemble the flotilla, and lack of capital forced him to act as broker for other merchants, taking a percentage on their profits. Nolan’s shipwreck forced Wilkinson to appeal to his creditors in January 1791 for an extension on his loans.
Writing to his most insistent lender, he admitted that half the expected amount of tobacco had been sold in 1790, and instead of a profit of ten thousand dollars he had lost six thousand dollars on the season. His despair at defaulting on his loans was unmistakable even through his habitually high-flown language. The prospect, he said “appalled my Spirit, and filled my mind with an horror not easily to be subdued. The conflict now is over, my spirit is broken, and I kiss the rod of humiliation.” As security, he could offer only the profit he expected to make on marketing a hundred hogsheads of tobacco in 1791. “I have but one stake left,” he pleaded, “if I give that out of my hands, my race is run, and all my prospects in life must speedily be terminated.”
Unfortunately for him, the creditor he addressed was the flint- hearted La Cassagne, who had sold the Wilkinsons their Louisville house. Although professing to be deeply moved by the plea—“not only because my own interests are materially affected, but because you must thereby be subject to innumerable pangs— which must destroy in a great measure that peace of mind which you have long laboured to secure”— La Cassagne behaved like a shark. The loan would be extended only if it was guaranteed by the wealthy Peyton Short, and the terms would include charging interest not just on the principal but on the interest already accrued. Together with other loans he had backed, Short was left liable for nine thousand dollars, and Wilkinson’s next three largest creditors were owed another thirteen thousand dollars. Even with this burden hanging over him, he might have carried on trading.
Secretly Wilkinson sent Hugh McIlvain, who was owed five thousand dollars, to New Orleans with two hundred hogsheads of tobacco, equivalent to roughly two hundred thousand pounds. But this sale also failed. Not only was much of the cargo in poor condition, but in 1791 Madrid arbitrarily capped sales of tobacco in New Orleans at forty thousand pounds. Wilkinson’s days as a trader were over. The former brigadier general was equipped for only one other profession. Showing an uncharacteristic practicality, he had already made preparations to return to a way of life for which he was better suited.
IN LATE OCTOBER 1790, the torrent of settlers spreading into the Ohio Valley provoked a backlash. Under the outstanding fighter Little Turtle, a 1,500- strong army was assembled from Native American tribes in the area south of Lake Erie, and in a series of ambushes and skirmishes it destroyed a U.S. column of 320 regular soldiers and more than 1,000 militia under General Josiah Harmar. Although the defeat occurred far to the northwest of Cincinnati, it posed a clear threat to Kentucky’s settlers, and Wilkinson immediately volunteered to lead a column of volunteers in a retaliatory attack.
“The voice of all ranks called me,” he told Miró, always his faithful confidant. Although winter was coming, he promised to lead them through “all obstacles arising from the inclemency of the season, from Frost, from Ice &Snow, from deep and Rapid Rivers.” He had, however, overestimated his popularity. Not until the spring of 1791 did the Kentucky committee, the embryonic state’s governing body, authorize a punitive raid, and the command was given to General Charles Scott, with Wilkinson only second-in-command. The raiders consisted of about eight hundred horsemen, and in six weeks they destroyed dozens of villages, killed scores of Indians, and burned hundreds of acres of young corn. Wilkinson took independent command of a party responsible for torching several habitations, taking thirty- two lives and seizing fifty-four captives. Back in Kentucky, the raid was counted such a success that a second was called for before the summer was over. This time the Kentucky committee put Wilkinson in command. About five hundred volunteers followed him on a daring expedition deep into Indian territory as far as the Wabash and Eel rivers, near modern Logansport, Indiana. There they burned the Kickapoo village of Anguile and surrounding cornfields and killed or captured forty-two Indians. Reporting to the president, Henry Knox, the secretary of war, commented approvingly, “The consternation arising from the demonstration of their being within our reach must all tend to the great object, the establishment of peace.” He also alluded to Wilkinson’s letter sent on August 26 expressing a desire “to enter the military service of the United States.”
Wilkinson was never wholly honest about his motives for any major decision, and the guise that he presented to Knox was that of a patriotic frontiersman anxious to serve his country. “During a residence of more than seven years in these woods, I have spared no pains, nor no expence to make myself acquainted, with the extensive regions watered by the Mississippi, and its tributary streams,” he wrote. “I have personally explored much of this extensive tract, have acquired an exact knowledge of a great part and a general knowledge of the whole— It is my wish to be employed in some station in which I may be able to employ and apply my information, and my small abilities to the public advantage, and my own honor.” The station he had in mind was command of the new regiment that Congress authorized to be raised in response to Harmar’s defeat.