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Born in 1747 in Oporto, Portugal, the wine-exporting coastal town where his father was Spanish consul-general, Gayoso always identified himself as a native of Pontevedra, site of his family’s estate in Galicia. Educated at Westminster College in England, Gayoso retained, according to his American neighbors in Natchez, “the manners and customs of that nation … especially in his style of living.” A career soldier with a flair for diplomacy and a good understanding of languages, law, economics, and politics, Gayoso advanced rapidly under Carlos III. His was the kind of talent that senior officials coveted. While serving as an officer on the warship
La España
during the Spanish siege of Gibraltar of 1779–1783, General Alexander O’Reilly (whose many accomplishments included the imposition of Spanish rule in Louisiana in 1768) recognized his linguistic and diplomatic skills and recruited him as an aide-de-camp.
43

Promoted to captain, Gayoso learned the art of civilian administration at O’Reilly’s side during his tenure as governor of Cádiz from 1779 to 1786—except when he was polishing his diplomatic talents in Lisbon, where the Spanish ambassador “borrowed” him for months at a time (and
where he also met and married the beautiful Theresa Margarita Hopman y Pereira). Not surprisingly, when the minister of the Indies cast about for the right officer to command the new district at Natchez, he found “that all the necessary qualities for this task are combined in the person of Lieutenant-colonel and Adjutant of the Plaza of Cadiz, Don Manuel Gayoso de Lemos.” Gayoso spent October and November 1787 in Madrid, studying Miró’s reports and correspondence from Louisiana and conferring with Floridablanca and Carlos Ill’s senior ministers.
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Prompted in part by Diego de Gardoqui’s inability to achieve a treaty that closed the Mississippi to American traders, in part by the pressure of American settlements west of the Appalachians, in part by the advice of New Orleans officials such as Martín Navarro and Esteban Miró, and in part by the vacillation that accompanied the death of Carlos III, Spain was lurching toward new defensive policies for the Lower Mississippi. As early as May 1788, Floridablanca had floated a trial balloon to Gardoqui. If Spain could no longer keep the Americans from using the river, Floridablanca wondered, why not

attract to our side the inhabitants of the Ohio and Mississippi, be it by alliance, by placing them under the protection of the King, or through union with his dominions under treaties which will insure their liberty, thus allowing them to export their products to New Orleans and to provide themselves at that town with goods they need from other countries.
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Gayoso was fully briefed by Floridablanca before the death of Carlos III and encouraged to communicate directly to the ministry in Spain.

After many delays—including the birth of Manuel and Theresa Gayoso’s first child, a difficult passage across the Atlantic, storms in the Gulf of Mexico, and a lengthy stop at Havana so that Gayoso could explain the nature of his mission and the evolving defensive policy to the captain-general of Cuba (Miró’s and Carondelet’s superior in the imperial chain of command)—the small brig
La Industria
moored near Grand Route St. John. On April 12, 1789, the new governor of Natchez stepped ashore to greet his old friend and comrade, Esteban Miró. The governor of Louisiana would soon return to Spain, and his successor, Carondelet, would come and go—dispatched after his six-year tenure in New Orleans to Quito, Ecuador, where he died in 1807.
46
As governor of Natchez until 1797 and then governor of Louisiana until he succumbed to yellow fever in July 1799, Manuel Gayoso de Lemos represented Spain’s best hope of controlling the Mississippi River for a few more years.

*
Wittol:
a cuckold who knows of his wife’s infidelity and submits to it.

— CHAPTER SEVEN —
Questions of Loyalty

I hope that no one can say of me with justice that I break any law of nature or of nations, of conscience or of honor, in transferring my allegiance, from the United States to his Catholic Majesty.

—James Wilkinson, August 22, 1787
1

He has compromised himself entirely, so that should he not succeed in severing Kentucky from the United States, he will not be able to stay there, unless he has suppressed those articles which might be injurious to him

a possible procedure.

—Governor Esteban Rodríguez Miró, April 17, 1789
2

That I have ever, in all my correspondence and intercourse with the Spanish government, conceded a tittle of the honour or interests of my own country, I most solemnly deny, in the face of God and man.

—James Wilkinson,
Memoirs of My Own Time,
1816
3

T
HE ROBUST
American officer who came downriver to meet Governor Esteban Rodríguez Miró in New Orleans on July 2, 1787, was a perfect chameleon. Born in 1757 at Hunting Creek, near the tidal waters of the Patuxent River on Maryland’s western shore, James Wilkinson had begun studying medicine with a local physician at fourteen. By 1774 he was enrolled at the College of Philadelphia, America’s best medical school, and was practicing at the Pennsylvania Hospital. A few blocks away, the buzz of revolutionary politics at the First Continental Congress in Carpenter’s Hall and the flash of bright uniforms in the city’s patriot encampments caught the young physician’s fancy. “Arms,” James Wilkinson
decided, would be “his profession and politics his hobby”—and thereafter he managed both with amazing dexterity
4

By December 1783, when Brigadier-General Wilkinson arrived in Kentucky as the accredited mercantile representative of Barclay, Moylan & Co., of Philadelphia, his career had already demonstrated a bent for intrigue. “Some men are sordid, some vain, some ambitious,” he once told Diego de Gardoqui. “To detect the predominant passion, to lay hold of it, is the profound part of political science.” Wilkinson knew whereof he spoke. He had served closely with Benedict Arnold in the invasion of Quebec and with Horatio Gates when Burgoyne surrendered at Saratoga, and he was deeply involved in the so-called Conway Cabal of 1777, a purported scheme to replace Washington with Gates as commander in chief. Most recently he had resigned as clothier-general of the army in 1781 amid charges of irregularities in his accounts.
5

“Not quite tall enough to be perfectly elegant,” a hostile contemporary thought, but “compensated by symmetry and [the] appearance of health and strength,” Wilkinson exhibited a face “beaming with intelligence.” His manners were “gracious and polite,” he spoke persuasively and wrote with florid eloquence and superb penmanship, and “by these fair terms he conciliated; by these he captivated.”
6
Relying on his knack for persuading someone to hear more than he actually said and, equally important, on a good memory for the prodigious array of targeted exaggeration, omission, partial truth, and insinuation that comprised his vocabulary of intrigue, James Wilkinson positioned himself as frontier Kentucky’s man of the hour.

When Wilkinson arrived in Lexington, the two major issues in the rapidly growing Kentucky district were access to markets down the Mississippi and the prospect of statehood. (The latter, in part, offered better frontier defense against the Indians than state officials in the Virginia capital at Richmond, five hundred miles to the east, were able to provide.) Vaguely authorized by a series of enabling acts passed by the General Assembly of Virginia, Kentuckians held nine or ten statehood conventions between November 1784 and the state’s eventual admission to the union in 1792. Wilkinson arrived in time to witness the third convention, in May 1785, and to win a seat in the fourth that August, which, as had become customary, petitioned the legislature of Virginia for an act “declaring and acknowledging the independence of the District of Kentucky”
7
Or so it seemed.

In May, the third convention had linked its call for separation from Virginia with the expectation of acceptance into the union as a fourteenth state. The August petition and address to the people of Kentucky and
Virginia, written by none other than James Wilkinson in what he described as the “plain, manly, and unadorned language of independence” (actually the rococo eloquence he customarily employed for intrigue), called for Kentucky independence but
not
for admission to the union.
8
By Wilkinson’s design and the convention’s inadvertence, the Kentucky resolution ignited an imperceptible spark that unforeseen events helped Wilkinson fan into the famous “Spanish Conspiracy.”

Beaming from the canvas of this 1813 oil portrait by John Wesley Jarvis, the robust face of General James Wilkinson offers no hint of the shadows in his remarkable career. Implicated in the Conway Cabal against General Washington during the Revolution, the Maryland-born Wilkinson moved to Kentucky after the war, negotiated a lucrative Spanish pension and trade privileges down the Mississippi, and schemed to separate Kentucky from the union in the 1780s. Soon after helping to secure the transfer of Louisiana to the United States in December 1803, Wilkinson began plotting with Vice President Aaron Burr to bring an expedition downriver to New Orleans, ransack the city’s banks, and thereby finance their conquest of Mexico. Participants were “as greedy after plunder as ever the old Romans were”

“Mexico glitters in our Eyes.” The plot gained momentum after Burr killed Alexander Hamilton in 1804 but eventually collapsed after Wilkinson reported it to President Jefferson and then became the principal witness at Burr’s trial in 1807. Wilkinson was summoned before a court of inquiry in
1815
on a range of charges, including neglect of duty along the Canadian border during the War of 1812. Acquitted and honorably discharged from the army, he died penniless in Mexico City on December 28,
1825. (Courtesy Historic New Orleans Collection, ace. no. 1991.3)

Entirely ignoring the omitted clauses in the Kentucky petition, on January 6, 1786, the legislature of Virginia passed another enabling act for Kentucky statehood, with a clear twenty-month schedule. A fifth convention was to meet at Danville, Kentucky, in September 1786. If that convention endorsed statehood, then Kentucky needed to adopt a suitable constitution and by June 1787 obtain consent from Congress to join the Confederation. Once these steps were taken, Virginia was willing to relinquish its authority over the Kentucky district as early as September 1, 1787.
9

The timetable could not have been more ill-fated. The Massachusetts delegation was using the Jay-Gardoqui negotiations secretly to push the southern states out of the Confederation, and when everything came to a head in August 1786 the sectional deadlock in Congress killed any hope of approval for Kentucky statehood. Later, as the Confederation Congress continued its drift toward insolvency, major issues like statehood for Kentucky were deferred until the Philadelphia convention drafted and nine states ratified the new Constitution.

Early in 1787, the two-year-old spark from James Wilkinson’s petition began to glow. That January a letter from Richmond was carried down the Ohio and Kentucky Rivers to Buck Pond, the home of fifty-seven-year-old Thomas Marshall, who had come to Fayette County as a surveyor in 1781. Marshall’s son John, then a member of the General Assembly of Virginia (and later chief justice of the United States), alarmed his father with news out of Congress that the seven northern states were threatening to barter away American navigation rights to the Mississippi River. Soon thereafter, the Scots-born and Virginia-trained chief justice of the Kentucky district court, George Muter, opened a letter from Congressman James Madison asking, “Would Kentucky purchase a free use of the Mississippi at the price of its occlusion for any term, however short?” From these and countless other sources, the dire news spread, and it provoked exactly the kind of anger that Rufus King and the Massachusetts separatists had expected. A resident of Louisville
exclaimed that news of “the late commercial treaty with Spain has given the western Country an universal shock, and struck its Inhabitants with an amazement.”
10

“I have not mett with one man,” Judge Muter hastily replied to Madison, “who would be willing to give the navigation up, for ever so short a time, on any terms whatever.” Kentucky attorney general Harry Innes, a transplanted Virginian who had attended the College of New Jersey with James Madison, read law with George Wythe, and practiced in the Old Dominion for ten years before moving to Kentucky, warned the governor of Virginia that “this western country will, in a few years, Revolt from the Union and endeavor to erect an Independent Government.” The Reverend Caleb Wallace, another of Madison’s classmates at Princeton, who was formerly affiliated with the Hanover Presbytery in Virginia and was now a judge of the district court, predicted that Kentucky would declare “absolute independence” if Congress failed to offer statehood. “Freedom from State and Federal obligations would enable us to govern and defend ourselves to advantage,” he continued, because “we should no longer be in subjection to those who have an interest different from us.” These were the voices of reasonable and responsible elected leaders who gathered in conventions to chart the district’s future. When Kentuckians gathered at court days and church services, at militia musters and squirrel hunts, however, impatient voices could also be heard echoing Wilkinson’s boast that “the People of Kentucky alone, unaided by Congress in any particular whatever, could dislodge every Garrison the Spaniards have on or in the neighborhood of the Mississippi… with ease and certainty”
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