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Although Wilkinson proclaimed that “a Free Trade out of the Mississippi” was the “inestimable prize [for which] we are all unanimously ready to wade … through Blood,”
12
attacking New Orleans at the head of an army of Kentucky militiamen was not his plan. Flatboat diplomacy was. Late in 1786, with help from John Marshall, Wilkinson sought a passport from the governor of Virginia for a journey down the Mississippi—and about the same time he attempted, through Baron von Steuben, to get a passport from Diego de Gardoqui. Formal authorization to travel into Louisiana might have been convenient, but neither request was successful, so before leaving Kentucky on December 20, 1786, Wilkinson dispatched a personal letter written in French to the Spanish commandant at St. Louis, Francisco Cruzat.
13

Why French? Perhaps the lingua franca of European court diplomacy was intended to make a good impression, or perhaps to shield the letter’s contents from curious eyes. Or both. If Cruzat or his superiors wondered about the identity of this new informant, Wilkinson’s letter did not
expressly claim any authority beyond that of a private citizen. Surely Cruzat could be counted upon to draw his own conclusions when Wilkinson’s letter happened to arrive with the same courier, “a brother in arms,” who brought Cruzat a separate note from a man in Louisville who chanced to describe himself as a friend of “General Wilkinson’s.”
14

“I venture to assure you that the outrage recently committed against the property of a Spanish merchant at the post of Vincennes,” Wilkinson purred, “is generally disavowed here, and is the work of only a small number of unprincipled men under the command of General [George Rogers] Clark”—who had captured three Spanish boats in retaliation for the Spanish seizure of Thomas Ormis’s boats at Natchez in June 1786. “At this very moment,” Wilkinson volunteered, “a certain Colonel Green and other desperate adventurers are meditating an attack on the posts of his most Catholic Majesty at Natchez.” If the Spanish commander at St. Louis got the impression that Wilkinson’s promise to “do everything in our power here to foil this band” came from a Kentucky officeholder, that was just fine. If Wilkinson’s warning gave Cruzat “time to inform his Excellency, Don Miró, of [Green’s] projected plan” and of Wilkinson’s help in thwarting it, so much the better.
15

Lacking formal passports from Virginia or from Gardoqui, in April Wilkinson set off for Louisiana on a tide of bravado, with a cargo of hams, butter, and tobacco (all contributed for the purpose without any investment by Wilkinson) and a pair of fine horses. “Loudly exclaiming in the mean time against restraints on the rights of navigation and free trade,” according to an eyewitness, Wilkinson left “his countrymen enraptured with his spirit of free enterprise and liberality, no less than his unbounded patriotism.”
16

On June 16, 1787, the glib American arrived at Natchez in a canoe, accompanied by Captain Carberry (the “Gentleman of the late American Army” who had carried Wilkinson’s first letters to St. Louis), one slave, and an
enganchado,
or boatman. Carlos de Grand-Pré, the Spanish commander of Fort Panmure, at Natchez, duly advised Governor Miró that he had given Wilkinson “a room in this fort, entertaining him to the best of my ability, since this officer is a very worthy person in every respect.” Wilkinson was “awaiting here a big barge, which should arrive today,” Grand-Pré continued, “in order to continue with it his voyage to [New Orleans], where he is to embark for Philadelphia.” The commander saw no need to mention Wilkinson’s friendly gift of the two fine horses.
17

At Natchez Wilkinson apparently transferred his remaining cargo onto flatboats, perhaps as many as five of them, before going on to New Orleans. While the evidence about some details of Wilkinson’s journey
is contradictory, it is certain that the general reached New Orleans on July 2, 1787—as did Grand-Pré’s letter warning Miró of his imminent arrival. Escorted directly to the governor’s office by a Spanish corporal, Wilkinson quickly impressed Miró and Intendant Navarro as “a person endowed with high talents” whose influence in Kentucky might prove useful for the defense of Louisiana. Portraying himself as the man “in whom the [Kentucky] settlements have placed their hope of future happiness,” Wilkinson “informed the governor and myself,” Navarro wrote, “that it was the[ir] intention … to put themselves under the protection or vassalage of his Catholic Majesty.”
18
On the chance that Wilkinson might be able to deliver on this promise, Miró and Navarro allowed him to sell his cargo and began a series of secret conversations, lasting into September, that launched the Spanish Conspiracy.

Two months into their negotiations, on August 22, 1787, James Wilkinson wrote and signed a formal document “transferring [his] allegiance, from the United States to his Catholic Majesty.” “Born and educated in America,” Wilkinson wrote,

I embraced her cause in the recent revolution, and steadfastly I adhered to her interests until she triumphed over her enemy. This event, having rendered my services no longer needful, released me from my engagements … and left me at liberty, having fought for her welfare, to seek my own. Since the circumstances and policy of the United States have rendered it impossible for me to attain this desired object under her government, I am resolved, without wishing them any harm, to seek it [with] Spain.
19

During the course of his secret talks at the government house on St. Louis Street, Wilkinson also wrote a lengthy essay describing the western situation and his plan for Kentucky’s separation from the United States and subordination to Spain.

New Orleans can be a gossipy village, but Miró and Navarro protected Wilkinson and their negotiations about Kentucky separatism with a cover story to dispel “the excessive curiosity of the prominent men of this capital.” They “insinuated that Wilkinson came as a commissioner of the settlements to solicit a general permission to send down their produce.” The disinformation spread quickly, “the good effect of which is that nobody has imagined anything else.”
20

Ostensibly, Wilkinson’s
Memorial
(as the document has come to be known) recommended to Miró and Navarro “what ought to be the policy of the Spanish Court at this critical juncture.” In fact, with their help, the
Memorial
was written so that they could forward it to Spain. It opened with a review of the rapid growth of the western settlements, their dependence on the Mississippi River to counterbalance “those commercial advantages which their Brethren on the Atlantic enjoy,” and the American Confederation’s inability to protect western interests. Kentucky independence was inevitable, Wilkinson contended. When it came, Spain would have two options. On the one hand, “an accommodating deportment” could entice Kentucky to become “subservient to the interest of Spain.” On the other, “hostile restraints” would surely “drive them into the arms of Great Britain.”
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“If Spain drives the Americans into the arms of Great Britain,” Wilkinson warned, “she immediately endangers her Louisianian territories, and eventually her Mexican provinces,” but “if she attaches the Americans to her interests,” Kentucky would serve as “a permanent barrier against Great Britain and the United States.” As things stood, it was essential that Diego de Gardoqui “absolutely refuse to Congress the Navigation of the Mississippi,” Wilkinson advised, “for should this Gentleman form a treaty by which the Americans may become intitled to the independent enjoyment of this Navigation, he will destroy the power which Spain now enjoys over the American settlements, and entirely defeat our principal” objective. It was “an absolute Fact that these Settlements will… look up for protection to that power which secures them this most precious privilege.” Therefore, let Spain “carefully preserve this right to herself, until she can employ it in exchange for such concessions as she may think proper to demand from the western settlers of America.”

Opening the river
“generally”
to American trade—Wilkinson underlined the word—was contrary to Spain’s best interests, and his own: “The prohibition of intercourse by the Mississippi… should be still supported, generally, with as much rigor as ever,” he advised, but with one or two carefully chosen exceptions. “In order to conciliate and prepare the Minds of the western Americans for the grand object of these speculations,” he wrote, “it may be politic … to offer indulgence to men of real influence.” If Miró and Navarro could grant special trading privileges to one or two prominent Kentuckians (men like Brigadier General James Wilkinson leapt to mind) surely that valuable “indulgence”
monopoly
is such an ugly word!) “would attach the leading characters in that Country to the interest of Spain.” What’s more, the benefits of trading privileges would surely trickle down from the favorites, “cheer the People with the hope of a free and friendly intercourse,” dissuade them from “outrage
and hostility,” and pave the way for a “transition from the renouncement of the federal Government of America to a Negociation with the Court of Spain” that would be “natural and immediate.”
22

“Know then,” Wilkinson’s
Memorial
asserted, “that the leading characters of Kentucky… urged and intreated my voyage hither, in order to … discover … whether [Spain] would be willing to open a negociation for our admission
to her protection as subjects”
(Wilkinson’s emphasis). Accordingly, if Miró and Navarro agreed to the propositions they had helped him write, Wilkinson promised to return to Kentucky and “exert my political weight and influence to familiarize and recommend to the Body of the People among whom I live those views which constitute the design of my present voyage, and which have already fixed the attention of the discerning part of that Community.” His final request was for “the most inviolable secrecy” in all that he proposed.
23

“Gentlemen,” he reminded Miró and Navarro, “I have committed secrets of an important nature, such as would, were they divulged destroy my Fame and Fortune forever. … If the plan should eventually be rejected by the Court, I must rely on the candor and high honor of a dignified Minister to bury these communications in eternal oblivion.”
24

How rare and pleasant are the moments when national and personal interests honestly mesh. How generously Wilkinson offered to send down from Kentucky cargoes comprising

Negroes, live Stock, tobacco, Flour, Bacon, Lard, Butter, Cheese, tallow, [and] Apples [in] the amount of fifty or sixty thousand Dollars … which articles may be sold for my account, and the proceeds held by his Excellency the Governor, as a pledge for my good conduct until the issue of our plans is known, or I have fixed my residence in Louisiana.

How intelligently—the very next day—Miró and Navarro encouraged their undercover agent by accepting his trade proposal, “though not to exceed half of the sum he had suggested.” How shrewdly the governor and intendant protected the crown by investing their own money, as silent partners, in the cover operation of buying tobacco at $2 per hundredweight in Kentucky and selling it for $10 in New Orleans. And later, when Wilkinson’s first shipment arrived and he asked for immediate payment rather than leaving his money on account, how sensibly Miró “determined to gratify him on this occasion.” Compared to “the mischief that might arise from vexing him” or the “impediments that a lack of
money would doubtless put in the way of his operations,” how wise of Governor Miró to forgo “the greater security we might have in keeping his money in the treasury.”
25

On Monday, September 17, 1787, thirty-nine members of the Constitutional Convention in Philadelphia signed their newly drafted plan of government and recommended it to Congress and the states. By replacing the Confederation Congress with a more vigorous national government, their handiwork eventually contributed to the opening of the Mississippi and the demise of Wilkinson’s Spanish Conspiracy. Two days later, in New Orleans, General James Wilkinson bade farewell to Miró and Navarro and boarded a ship for Charleston. Among his papers was the key to one of Spain’s “most incomprehensible ciphers” so that he could communicate with Miró when he got back to Kentucky. The chosen code happened to be Number 13 in the series of Spanish ciphers, which led to Wilkinson’s designation as Agent 13 in his continued dealings with Spain during the next fifteen years.
26

In forwarding Wilkinson’s lengthy
Memorial
to the ministry in Spain, Miró and Navarro asked permission to support Wilkinson’s plans to separate Kentucky from the United States and to encourage Americans to settle in Louisiana as subjects of His Most Catholic Majesty. It suited Wilkinson’s purposes to regard both aspects as integral to his plans, but the governor and the intendant had equally good reasons to see them as distinct alternatives. Wilkinson, after all, was not alone in his ability to detect a predominant passion and lay hold of it. He had given Miró and Navarro plenty of reason to suspect that his grand promises cloaked a more selfish and less ambitious short-term interest in monopolizing the riverborne trade out of Kentucky—they suspected that his “grandiose undertakings” were meant to disguise “a means of realizing a profitable commercial speculation.”
27

In letters both to Miró and to Gardoqui, Wilkinson vigorously urged the Spanish to keep the river closed to American trade—despite the outrage that he had expressed and fomented in Kentucky on the eve of his first visit to New Orleans. Ostensibly his goal was “to alienate and eradicate american principles and connexions” among his Kentucky neighbors, but Miró and Navarro were not blind to the fact that by keeping the river closed to others, the value of Wilkinson’s special trading privileges increased. Only time would tell which goal figured more prominently in Wilkinson’s heart. The Spaniards watched him closely, and they soon concluded that Wilkinson was a better informant than agent provocateur.
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