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

by Andro Linklater

  Recognizing the situation, Miró 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, Miró 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,” Miró 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 Miró 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-Pré as governor of Natchez in 1789, Wilkinson at once sent him two dictionaries, so that he and “our Friend below,” meaning Miró, 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 Miró, “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? Miró’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, 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.

  Replying almost at once, Knox sent a congratulatory message “in the name of the President of the United States, for the zeal, perseverance and good conduct manifested by you in the Command of the expedition, and for the humanity observed towards the prisoners whom you captured; and also to thank the officers and privates of volunteers, for their activity and bravery while under your command.”

  With such an endorsement and his record in the Revolutionary War in his favor, Wilkinson’s suitability to command the new regiment should not have been in doubt. Against him, however, was a letter sent by Thomas Marshall, father of John and uncle of Humphrey, to George Washington in October 1789 in which he sketched the outline of the Spanish conspiracy “to effect a violent seperation from the United States.” The accusation was largely based on Marshall’s memory—“not very accurate,” he admitted— of the proposals for independence Wilkinson had put before the 1788 Danville convention. Although these were not secret, Marshall insisted he had seen a letter from Miró promising to place Wilkinson’s ideas “before the king of Spain.” To this message, Washington had replied, “I was greatly alarmed at the nature of the transactions mentioned in it . . . It is true I had previously received some verbal and written information on the subject of a similar tenor; but none which placed the affair in such an alarming point of view.” He begged Marshall to keep him informed of Wilkinson’s actions.

  Two years later, the president had heard no more from Marshall, but further allegations had come from another, less reliable source. James O’Fallon acted as agent to the South Carolina land company that was attempting to bribe the Georgia legislature into selling it twenty million acres of land on the Yazoo River. In September 1790 he warned the president, among others, that “an influential American has been engaged in trade to New Orleans and now acts the part of secret Agent for Spain in Kentucky.” Although there could be no doubt about the agent’s identity, Washington made no public comment. Presumably, he suspected the motives of a notoriously unreliable source. Nevertheless, he had now heard two specific charges about Wilkinson’s collusion with Spain.

  Weighing the allegations against the clear evidence of Wilkinson’s ability, the president came to a fateful decision. Writing to Alexander Hamilton, always his closest confidant in military matters, he stated his belief that Wilkinson had behaved foolishly, but not illegally. Demonstrating a sound grasp of human psychology, Washington explained that it was “expedient” to give him command of the regiment: “To hold a post of such responsibility would feed his ambition, soothe his vanity, and by arresting discontent produce a good effect.” All this was true, but lacking Miró’s intimacy with the man, he did not appreciate that Wilkinson’s true life took place at a different level.

  What had begun four years earlier as an expression of loyalty to Spain designed to finesse lucrative privileges from its uncertain empire had imperceptibly become a reality. “Some men are sordid, some vain, some ambitious,” he had declared in his 1787 memorial. “To detect the predominant passion, to lay hold and to make the most of it is the most profound secret of political science.” In this case, it was Miró who had found the secret. Trapped by economic need and emotional attachment, James Wilkinson had become Spain’s man. No matter what encouragement he was given by the president, the new lieutenant colonel would still dissemble.

  THE ARMY THAT General James Wilkinson had left in 1781 came to an end on December 23, 1783, in the delicate blue- and-white symmetry of Maryland’s Senate chamber in Annapolis. Shortly after midday, its commander in chief bowed to the members of Congress, who were his political masters, and announced in balanced phrases suitable to his surroundings that he was laying down his command: “Happy in the confirmation of our Independence and Sovereignty, and pleased with the oppertunity afforded the United States of becoming a respectable Nation, I resign with satisfaction the Appointment I accepted with diffidence.”

  It was the last act in the slow dissolution of the great force created to win independence that at its peak had a nominal strength of thirty- five thousand men, though closer to twenty-five thousand in practice. From the beginning of 1783, recruiting had gradually ceased, soldiers on two-and three- year terms did not have their enlistments extended, and men sent home on furlough were no longer expected to report back. Constantly pushed to make greater economies by a virtually bankrupt Congress, the army reduced regiments to companies, amalgamated five or six companies to make a new regiment, then demobilized that, too.

  The approaching end was so obvious in March 1783 that officers grew anxious they were about to be returned to civilian life before Congress had fulfilled its promise to make up pay arrears or guarantee a pension for their service. In their main camp at Newburgh, New York, a document was circulated that urged them to threaten a strike unless their demands were met—“[Tell Congress] that though despair itself can never drive you into dishonour, it may drive you from the field.” For a brief ten days the heroic defenders of liberty took on the hideous mask of a standing army that could bully a democratic
government into doing its will.

  The threat was defused by a moment of pathos— Washington strained to read a speech of reproof to the assembled officers, then remarked as he put on a pair of spectacles that he had grown gray in service of the Revolution and was now going blind as well. The sight of their unshakable commander’s frailty took the sting from his listeners’ resentment, and when Congress belatedly agreed to pay them five years’ salary in place of a pension, the mutiny collapsed. But the Newburgh address’s call to officers to play upon “the fears of government” continued to haunt Congress.

  Vainly Washington pleaded for a peacetime army of four professional regiments, supported by a militia trained to a uniform standard of discipline. Congress promised nothing. Even with the army reduced to the small number of men whose terms of enlistment ran into 1784, no move was made to authorize any kind of replacement. Attention focused on the historic drama of Washington’s closing words in the Maryland Senate chamber—“bidding an Affectionate farewell to this August body under whose orders I have so long acted, I here offer my Commission, and take my leave of all the employments of public life”— but in reality his army had already ceased to exist.

  Repeated attempts to revive it failed. A proposed force of 900 men was rejected by Congress; one of 350 men suffered the same fate; the lowest point came on June 2, 1784, when Congress dismissed all but 55 artillerymen in West Point and another 25 in Fort Pitt, declaring, “Standing armies in time of peace are inconsistent with the principles of republican government, dangerous to the liberties of a free people, and generally converted into destructive engines for establishing despotism.”