Thus the paradox running through James Wilkinson’s career is the service he performed for the United States while he was unmistakably betraying it. That tortured relationship reached its peak with Thomas Jefferson, who not only confirmed Wilkinson as commander of the U.S. army, but appointed him to the posts of governor of Louisiana Territory and commissioner of Indian affairs. No president trusted Wilkinson more, or asked so much in return, or, at the apogee of Aaron Burr’s conspiracy, came closer to a catastrophic misjudgment of Wilkinson’s uncertain loyalties. As Congressman John Randolph pointed out, “The agency of the Army was the whole pivot on which that plot turned.” Why then did James Wilkinson choose to defend his country at the cost, as it turned out, of his career?
THE FEAR OF BEING FOUND out haunted the general throughout his life as a spy. His tradecraft was exemplary. He rarely met his handlers. He communicated through a wide range of ciphers and codes, some of which remain unbreakable because the source books have been lost. He took pains to ensure that his payment in silver dollars came hidden in casks of coffee and sugar and was laundered through banks and real estate deals. To explain away any transfers of money that came to light, he had a watertight cover story backed by forged documents and false testimonials showing them to be the outcome of commercial deals.
The effectiveness of his methods was such that although he faced four official investigations, and many more private and newspaper inquiries, none turned up any hard evidence that he had actually passed information on to Spain in return for money. Nevertheless, Wilkinson was well aware that in one area he remained vulnerable. He could do nothing about the bureaucratic efficiency of the Spanish imperial government.
Once deciphered, his reports were copied in duplicate, sometimes in triplicate, so that local officials in New Orleans, their regional superiors in Havana, and their central masters in Madrid would all be aware of what Agent 13, the key Spanish operative in North America, had to disclose. Repeatedly, he begged his handlers to destroy his letters, “to hide them in deepest oblivion.” When the empire began to crumble, his anxieties became acute. To reassure him, one of his last Spanish contacts, Governor Don Vizente Folch of West Florida, grandly promised him that every incriminating document had been sent to Havana, and “before the United States shall be in a position to conquer that capital, you and I, Jefferson, Madison, with all the secretaries of the different departments . . . will have made many days’ journey on the voyage to the other world.”
So it proved, and Wilkinson died before his secret was uncovered. But in the last years of the nineteenth century a cache of papers relating to his activities was found in Baton Rouge, Louisiana. Not until the first quarter of the twentieth century, however, when a succession of dogged historians began to dig through the estimated two hundred thousand documents sent back from Havana to Madrid in 1888, was the smoking gun found. Hundreds of letters, reports, comments, and assessments exchanged between Wilkinson, his handlers, and their superiors, the secretary of the Indies and the royal council in Madrid, testify to the scale and importance of his activities. Seventy years ago, they gave rise to two biographies that traced his life but shrank from exploring either the full extent of his treachery or the reasons why successive administrations were ready to tolerate and in some circumstances collude with his activities. To make real sense of the behavior detailed in those documents, it is necessary to see the world through his eyes, and to understand why he found it so rewarding to lead a double life.
HIS BITTEREST ENEMIES testified to his charm. According to an early Kentucky historian, Humphrey Marshall, who came to hate Wilkinson after being cheated on a land deal, the general was not only “easy, polite and gracious” but possessed that seductive trait of focusing “assured attention, cordiality and ease” on each person he talked to. His language was lively and inventive. In a letter to George Washington, Wilkinson dismissed an allegation of taking Spanish money as the sort of attack that was inevitable “in these times of general calumny, when slander on stilts stalks over the fences of reputation.” He was musical, widely read, and imaginative enough to choose the perfect present for those he wished to impress— maps and Indian artifacts for Jefferson, thoroughbred horses for a Spanish commandant, and an exotic Alpine strawberry plant for a frontier governor.
To explain his taste for espionage, a CIA profiler might apply the four classic motives for treachery—money, ideology, coercion, or excitement—and conclude that the general was driven by his fear of poverty and boredom. Probing more deeply, a psychologist might guess that the general’s infectious enthusiasm, intoxicating confidence, instinctive lying, and sudden contempt for rivals suggested a narcissistic personality.
Yet neither of these explanations quite captures the cold detachment that underlay the vanity, energy, and extravagance. Both as soldier and spy, Wilkinson always hungered for intelligence. It gave him a sense of power. He did not care about the source—gossip, maps, and explorers were equally acceptable—so long as it told him something about the love life of a rival, a path through the mountains, or the ground that a battle might be fought on. As a result, he possessed an exceptionally well-informed, clear-eyed view of the rapidly changing era in which he lived, and of the advantages to be wrung from it. When Aaron Burr expected his collaboration in a conspiracy to tear the United States apart, it was this calculating appraisal that shaped Wilkinson’s response.
It is impossible to deny the psychological fascination of James Wilkinson’s ability to live a double existence in public view for so many years. Indeed, to judge him by the dark canons of treachery, his long record as commander and spy must rank as one of the most extraordinary careers as a secret agent in the history of espionage. But the lasting value of his divided loyalty is the unique perspective it offers of the young, vulnerable republic taking shape and gathering strength. Viewed through General James Wilkinson’s chilly, binocular vision, the struggle to establish the identity of the United States appears as it really was, an uncertain adventure in dangerous times.
1
THE PENNILESS ARISTOCRAT
EXCESS WAS BRED INTO HIM. It showed in his large aspirations, his wild expenditure, his undisciplined behavior, and his gigantic autobiography. In Memoirs of My Own Times, James Wilkinson spread himself across more than two thousand highly colored pages, but, as he confessed to friends, he had still only been able “to glance at one fifth of my public life.”
A tendency to grandiose living was habitual in the society into which he was born on March 24, 1757, the colonial aristocracy of Maryland planters. His grandfather Joseph Wilkinson, a tobacco merchant from England, had arrived in the province in the early years of the eighteenth century. This was the era when Europeans suddenly realized that the great landmass of British America contained uncountable acres that could be surveyed and converted into property. Anyone with enough money to pay his passage might hope to own an estate that would have made him a squire or a petty lord in Europe. The result was a growing flood of immigrants, especially to the middle colonies of Maryland, Pennsylvania, and northern Virginia, that threatened to engulf the proprietorial rights of the great families, the Calverts, the Penns, and the Fairfaxes, who had overall possession of the land.
A sharp divide soon opened up between the established settlements near the coasts and rivers, where the ground was already measured out by the proprietors for sale or rent, and the interior where the poorer immigrants settled, often squatting rent-free on territory beyond the proprietors’ control. Banditti was the word commonly used to describe these savage incomers, mostly Presbyterian Scots-Irish from Ulster and Germans from the Palatine state in the Rhine valley, who occupied the land as though it were their own. William Byrd of Virginia compared them to “the Goths and Vandals of old,” while in Pennsylvania James Logan, in charge of the Penn family’s affairs, complained of the disrespect “these bold and indigent strangers” showed for eighteenth-century conventions, “saying as their excuse when challenged for titles [to property], that we had solicited for colonists and they had come accordingly.”