“Some men are sordid, some vain, some ambitious,” James Wilkinson wrote in 1787 in a secret memo meant for Spanish officials “To detect the prominent passion, to lay hold and to make the most of it is the most profound secret of political science.”

Some men, such as Wilkinson, are sordid, vain, and ambitious. Very few, however, are as brilliant as this reckless and dangerous man could be. People in his day just didn’t talk about “political science.” And if politics is science, then Wilkinson, as this thorough and thoroughly absorbing biography makes plain, was a scientist of a rare order—a mad scientist, perhaps, but a scientist nonetheless. He understood realpolitik as few Americans have. He detected the “prominent passions” of men, and he played on them with mind-boggling bravado.

Born in Maryland in 1757, Wilkinson joined the Continental Army, endearing himself to a string of higher-ups—Nathaniel Greene, Benedict Arnold, Horatio Gates—each of whom he would later “throw under the bus,” in contemporary parlance, as soon as it suited his purposes. By 1778, under Gates, Wilkinson was secretary to the Board of War, but here, as so often, he got ahead of himself. He became entangled in the so-called Conway Cabal, a conspiracy to replace Gen. George Washington, and was forced to resign. Yet the following year, with Washington’s approval, Wilkinson was appointed clothier general, though in 1781 he was forced out again, this time amid allegations of corruption.

In 1784, seeking new outlets for his limitless energy and visions of great wealth, Wilkinson set out for Kentucky. It was there that he wrote his memo to the Spanish authorities. Hoping to gain a monopoly on American trade on the Mississippi, he signed a document “transferring [his] allegiance from the United States to his Catholic Majesty.” As part of the same plot, he became Agent 13, a “pensioned” spy for the Spanish crown.

This arrangement did not prove as lucrative as he had hoped. By 1791, he was back in the uniform of the Continentals—without severing ties with his Spanish handlers. From brigadier general, he rose in five years to become the nation’s ranking Army officer and, in 1805 to 1806, he served as governor of the Louisiana Territory.

Through the presidencies of Washington, Adams, Jefferson, and Madison, Wilkinson managed to make himself indispensable, even when evidence of his treachery was placed before their very eyes. He also managed, through it all, to render service to his Spanish paymasters. Under Jefferson, for example, he leaked word that the president was preparing to dispatch Meriwether Lewis and William Clark on their expedition through lands still claimed by Spain. He urged Spanish authorities to “detach a sufficient body of chasseurs to intercept Captain Lewis and his party … and force them to retire or take them prisoners.” Unaware, Jefferson rewarded Wilkinson for other services by appointing him governor of Louisiana.

It was during this period that Wilkinson began conniving with Aaron Burr, with whom—not surprisingly—he discovered he had a good deal in common. Since moving to Kentucky, Wilkinson had engaged in efforts to persuade others to favor separation from Virginia and from the United States itself. Support for secession from Virginia was a popular position in Kentucky under the Articles of Confederation, in large part because Spain had prevented farmers from moving their crops down the Mississippi to New Orleans, and the weak government in Philadelphia had been unable to establish free trade down that vital waterway. But support for seceding from the Union was surprisingly popular, too, especially when drummed up by Wilkinson and others who, on the payroll of Spain, told Kentuckians they stood to gain more from Madrid than from Philadelphia.

As odd as this might sound today, what became known as the Spanish Conspiracy made perfect sense to lots of Anglo-American settlers in the Southwest. It also held appeal for narcissistic visionaries like Burr who, in the words of Anthony Merry, the British ambassador, wished “to effect a separation of the Western Part of the United States from that which lies between the Atlantick and the Mountains, in its whole extent.” Wilkinson seems to have entertained just such dreams himself and encouraged Burr in them, though to what extent remains unclear.

Burr’s plans changed through the years, of course, and no one really knows exactly what he intended to do at any given time. By 1803, however, when Spanish forces were massing along the disputed border of the Louisiana Purchase in present-day Texas, and U.S. troops were diverted to the west to counter them, Burr seems to have settled on seizing defenseless New Orleans in preparation for invading Mexico. With Wilkinson as second-in-command, Burr envisioned an empire of his own, composed of much of Mexico as well as the territories of the American west.

Reports of this plot were, of course, making their way back to Washington, putting Agent 13 in a very sticky spot. Casting his lot with the United States rather than Spain, Wilkinson, in November 1806, fired off a letter to Jefferson, warning him of a “deep, dark and wide-spread conspiracy, embracing the young and the old, the democrat and the federalist, the native and the foreigner, the patriot of ’76 and the exotic of yesterday, the opulent and the needy,” and pledging to use “indefatigable industry, incessant vigilance and hardy courage” to defend New Orleans. This Wilkinson did in spades, declaring martial law and rounding up his political enemies, including, especially, those who knew how deep in this “dark and wide-spread conspiracy” he had been. Once again, Wilkinson betrayed one of his fellow sneaks, testifying against Burr before a grand jury.

“He never won a battle,” it was said of Wilkinson, “or lost a court-martial.” That he escaped hanging is remarkable, considering how diligently he seemed to court it. But for one vote, he would have been indicted in the Burr conspiracy, and he was court martialed twice, in 1811 in connection with his dealings with Spain and in 1815, after a failed attack on Montreal in the War of 1812. Wilkinson was also investigated by Congress on a variety of charges, most of them true, but he scraped by. Even so, volumes of damaging information about his dealings came to light and eventually, as might be expected, his reputation was ruined. He died in 1825, in Mexico City, having lived out his days as an influence peddler with less and less influence to sell.

This heavily researched and otherwise admirable book is not without its flaws: Aaron Burr was never “the Federalist candidate for President,” nor was Virginia his “home state.” To his credit, Linklater does not labor to explain his subject’s devious character, though vague references to the role “psychology” played in Wilkinson’s lurid machinations rather beg the question. Probing the man’s peculiar mental processes would probably not have been fruitful. But a stronger exploration of the commercial and political realities of his time and place, which made it possible for Wilkinson to operate for as long as he did, could have been highly instructive.

The notion of “treason” could also have been better treated. To what authority can we fairly expect residents of the Kentucky District to have been undyingly loyal in 1788, when “patriots” North and South considered their states, and not the federal government, “my country”? What does it mean to accuse Wilkinson of treasonous activities in the 1780s when it was the Burr trial, almost a quarter of a century later, that defined the crime under American jurisprudence?

Linklater seems to argue that Wilkinson’s antics were possible as long as the country labored under a Jeffersonian “ideology” that viewed “standing armies” with suspicion. Corruption would be less likely under a “properly funded, professionally trained army,” with a “permanent general staff to take responsibility for military organization.” There would be “no place for General James Wilkinson in this modern age,” Linklater writes. He does not add that there would be plenty of room for scoundrels, opportunists, and conscienceless careerists of a different stripe.

There seems no doubt, from Linklater’s highly detailed reconstruction, that Wilkinson’s world had changed dramatically by the time he met his rather sad end in the suburbs of Mexico City. Once American settlers were free to move their crops down the Mississippi—a goal achieved under the Treaty of San Lorenzo in 1795—any significant support for Western secession had died, though Wilkinson never seemed to realize this.

The old man failed to understand that a new nationalism was taking form, perhaps because he was incapable of comprehending loyalty of any kind. This development also eluded Burr, which is one reason his grandiose schemes also ended so dismally. “The certainty of the national frontier drawn by Andrew Ellicott on 1798, the pride on the sudden doubling of the U.S. landmass through the Louisiana Purchase, and the guarantee of property rights under U.S. law that each settler depended upon,” Linklater writes, “had created something new, a clear attachment to the nation.” Old arguments from the Whiskey Rebellion days were no longer persuasive. The more bound Americans became to their central government, the less likely they were to be won over by appeals to throw in with a foreign power or to risk everything on a gamble.

This “clear attachment to the nation” still gave plenty of scope to adventurers. One of these, who had also flirted with Burr in his early secessionist fantasies, was arguably more ambitious than Wilkinson and decidedly more effective in achieving his objectives. This was Andrew Jackson of Tennessee whose views reflected those of a new generation. By 1807, Jackson professed disgust with any actions designed to benefit the Spanish empire or that might threaten the American nation. “I would delight to see Mexico reduced,” Jackson said, “but I will die in the last ditch before I would yield a foot to the Dons or see the union disunited.” In due course, this devotion to the union would face serious internal threats of a different nature, though not for another half century. 

Alan Pell Crawford is the author, most recently, of Twilight at Monticello: The Final Years of Thomas Jefferson.

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