the Ohio might do her good, and just before he departed for New Orleans, Wilkinson bought a half- acre lot in Louisville from an unreliable French- born speculator named Michael La Cassagne. Louisville was only a quarter of the size of Lexington, but from Nancy’s point of view it had the advantage of being on the Ohio, the main line of communication with the east. But like her hopes of seeing her family back in Philadelphia, the move would happen only if they had the money. In September 1789 when she began to expect her husband back, she wrote optimistically, “I think it Probable we shall spend Part of this Winter at the falls [Louisville], however it will depend greatly on My Jimmy’s Business.”
When Wilkinson returned at the end of October, they did indeed move to Louisville, but not because his business was thriving. Much of his most valuable real estate was put up for sale, “a valuable tract of land of 10,000 acres, together or in small parcels,” along with the livestock he kept on it, and “several houses and lots in this town [Lexington],” including the store. It was not quite a fire sale, but all of it was “to be sold for cash or exchanged for merchandise” as soon as possible.
10
ENSHACKLED BY DEBT
JAMES WILKINSON HAD TWO WEAKNESSES as a businessman— his readiness to mistake his gross profit for net gain, and his reluctance to prepare for the worst. On his 1787 voyage, when he had stayed so long in New Orleans, expenses ate up all but $377 of the $10,185 his cargo earned. The following year, tobacco sales brought in $16,372, but expenses, including almost $1,000 for boatmen’s wages, left only $6,251 in silver Mexican dollars for Abner Dunn, brother of his partner, to bring north. In 1789, Wilkinson sent down 342 hogsheads of tobacco, and although almost one third was found to be so rotten it could not be brought to market, the remainder sold for $18,131. Yet once Clark, an investor in the cargo, had been paid his share, Miro had taken his $3,000 cut, and Nolan had paid out other sums, just $49 was left in the Wilkinson and Dunn account. There was nothing to invest in next season’s trade. Whatever credit Wilkinson still had in Kentucky absolutely depended on the goodwill of New Orleans. Without Miro he could not survive.
Recognizing the situation, Miro had immediately authorized the seven-thousand-dollar loan without waiting for Madrid’s approval, even though both he and Wilkinson were aware that the drive had gone out of the separatist movement. “On my arrival here,” Wilkinson wrote from Louisville in early 1790, “I discovered a great change in those who had been so far our warmest friends. Many, who loudly repudiated all connection with the Union, now remain silent . . . At present, all our politicians seem to have fallen asleep. Buoyed up by the privilege of trade which has been granted to them on the Mississippi, the people think of nothing else than cultivating their lands and increasing their plantations.”
With the cool insight that characterized his dealings with Wilkinson, Miro commented to Valdes that while secession had certainly lost its impetus, the real problem was with Wilkinson. Faced with growing hostility to his views, he had simply backed down or avoided the subject. “The great falling off which I observe in his last letter,” Miro wrote, “induces me to believe that, full of good will and zeal, and persuaded, from the experience of past years, that he could bring round to his own opinions the chief men of Kentucky, he declared in anticipation that he had won over many of them, when he had never approached them on the main question.”
Under acute financial strain, with his popularity draining away, Wilkinson had in fact lost his political nerve. “I am justified in saying that Congress strongly suspects my connection with you,” he told Miro in February 1790, “and that it spies my movements in this section of the country . . . I am narrowly watched by the servants of General Washington.” When Manuel Gayoso de Lemos replaced Grand-Pre as governor of Natchez in 1789, Wilkinson at once sent him two dictionaries, so that he and “our Friend below,” meaning Miro, could communicate more safely; “I dare not hazard a word on politics but in Cypher.”
Looking for a way out of the mountain of debt that threatened to engulf him, Wilkinson reverted to the idea that had surfaced in his second memorial, of openly declaring his change of loyalties. “My situation is mortally painful,” he told Miro, “because, whilst I abhor all duplicity, I am obliged to dissemble. This makes me extremely desirous of resorting to some contrivance that will put me in a position, in which I flatter myself to be able to profess myself publicly the vassal of his Catholic Majesty, and therefore to claim his protection, in whatever public or private measures I may devise to promote the interest of the Crown.”
This posed a potentially awkward question: what should Spain do with a client politician who had lost his confidence, who no longer dared advocate secession, and who wanted to come clean about his past? Miro’s reply in April 1790 showed how well he understood his friend’s instinct for duplicity. “I much regret that General Washington and Congress suspect your connection with me,” he wrote coolly, “but it does not appear to me opportune that you declare yourself a Spaniard for the reasons which you state. I am of opinion that this idea of yours is not convenient, and that, on the contrary, it might have prejudicial results. Therefore, continue to dissemble . . .”
Three weeks later, Miro 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 Miro 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 Miro 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.”
