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The story is not entirely credible, and no evidence suggests that Miró took at face value, even though Wilkinson promised that he wrote “as a good Spaniard.” But the reminder that Spain could not afford to ignore Kentucky’s disaffected settlers served Miró’s purpose. Convinced that the threat they posed to Louisiana had to be neutralized, he regarded Gardoqui’s intervention as a piecemeal solution. His preferred strategy remained that put forward in Wilkinson’s memorial. That plan was Miró’s plan, just as Wilkinson was Miró’s man, and the Louisiana governor still pressed Madrid for a favorable response.

ADDING URGENCY TO Wilkinson’s appeal was a misfortune that had blasted his first hopes of growing rich from trade. In September 1788, the Speedwell, the ship carrying the cargo of luxuries that Clark, Dunn, and Wilkinson intended to sell to Kentuckians, left New Orleans. Its voyage upriver was slow, and she had only just entered the Ohio River in November. There she was caught by ice that formed unseasonably early that winter. Before her precious cargo could be off- loaded, the hull was crushed, and she sank to the bottom with Wilkinson’s investment of more than $6,000.

To recoup the expense, he assembled another, larger fleet to take goods down the Mississippi. Short of funds, he was forced to borrow from wealthy speculators such as John Lewis of Louisville, and the boats were sent south as soon as the ice began to break in the spring of 1789. When they arrived in New Orleans, the governor of Louisiana—“the man I love and the friend I can trust”—immediately agreed to buy 235,000 pounds of Wilkinson’s tobacco, “on the grounds” as Miró informed Madrid, “that it was important to keep the General contented.”

To calm Wilkinson’s fears that he was being displaced, Miró also found time in his fourteen-hour working day to write and assure him “that I still continue to hold you as the principal actor in our favor,” and to submit for his consideration Sevier’s proposal that the settlers in Tennessee should become Spanish subjects. “I hope that, gathering all the information which you may deem necessary,” Miró continued, “you will give me your opinion on this affair, in order that I may shape my course accordingly.” He signed himself “your most affectionate friend.”

Despite this reassurance, Wilkinson felt it necessary to see Miró in person and in June 1789 followed his boats down to New Orleans. He arrived to discover that his trading ambitions had suffered a second devastating blow. His partner, Isaac Dunn, had killed himself days earlier from despair at his wife’s infidelity and his own debts. Later, Wilkinson estimated his losses from the tragedy to have amounted to ten thousand dollars. He may have exaggerated, but not by much. At the end of the 1789 season, when Joseph Ballinger, a courier from New Orleans, arrived with two barrels of silver to pay the farmers of Lincoln County for the tobacco they had entrusted to Wilkinson, there was not enough to cover what was owed them. Their anger and abuse began the erosion of Wilkinson’s popularity in Kentucky.

The financial loss made him still more dependent on Miró’s goodwill, but to his alarm the royal council in Spain showed itself hostile to his secessionist plans. Its first direct reaction to his memorial was only delivered to New Orleans early in 1789. Both the eighteen-month delay and the woolly quality of the response help to explain Spain’s inability to deal with the swiftly changing events in the Mississippi basin. Demonstrating its failure to understand the central point of Wilkinson and Miró’s strategy, that access to the river was the key to political influence in the region, the council declared that the Mississippi should be opened to American trade, subject to a mere 15 percent duty on goods sold. Although this eliminated much of the settlers’ incentive to put themselves under Spanish rule, the council also declared that migration to Louisiana was to be encouraged. Finally, in a direct rebuff to Wilkinson and Miró, a ban was placed on any help being given to Kentucky’s secessionist movement.

The need to counter the damage of this new policy kept Wilkinson in New Orleans during the summer of 1789. Amid efforts to disentangle the legal mess left by Dunn’s suicide, he and Miró spent three months discussing the proper strategy for Spain to follow. The outcome was a second memorial, written in September. That it was a joint collaboration, not just with Miró but with the free-trade philosophy of Navarro, was apparent from a striking passage extolling free enterprise over Spain’s mercantile economy that restricted trade to its own colonies and ships: “Our navigation being confined at present to Spanish vessels, and our commerce to a few Spanish ports and islands, rivalry [i.e., competition], which is the vital principle of commerce, is dead, and the immediate consequences follow; our merchandise in dry goods [i.e., textiles and clothing] is now sold at from 75 per cent. to 150 per cent. more than in North America, and the freightage of one cask of tobacco from New Orleans to any part of Europe costs as much as four casks from any part of the United States to the same place.”

Their solution was to urge the council to make New Orleans a free port open to all trade from the sea, although river traffic would still be restricted. But by now the United States had both free enterprise, and, since the inauguration of George Washington as president in April, a democratic, federal government that “although untried and of doubtful success,” as Wilkinson grudgingly put it, “has inspired the people in general with the loftiest hopes.” Nevertheless, he believed a window of opportunity existed before this new, formidable entity could unify the conflicting ambitions of east and west. “To seize this interval,” he declared, “and to take advantage of the occasion are certainly the true policy of Spain, are my longings, are my desire.”

Some requirements remained unchanged—the Mississippi had to be closed, immigration encouraged, influential men given commercial advantages to illustrate the advantage of Spain’s protection—but the secessionist cause now had to overcome the effects of U.S. patronage. Many of Kentucky’s “notables,” once loudly in favor of independence, had fallen silent after being appointed as federal judges, revenue officers, or tax officials, so Spain should be ready to buy their loyalty back and pay them “to accomplish the above- mentioned separation and independence from the United States.” For a cost of twenty thousand dollars a year, Wilkinson estimated, Spain could procure the support of the most influential men in Kentucky. The alternative, as he bluntly predicted, was that “instead of forming a barrier for Louisiana and Mexico, [the settlers] will busy themselves in conquering the one and attacking the other.”

In a separate document, he provided a list of twenty-two people who should be offered bribes. Nearly all were either friends, such as Harry Innes, who, although a federal judge, “would much prefer to receive a pension from New Orleans than one from New York,” or enemies he wanted to buy off, such as Humphrey Marshall, once his partner but now suing him over a failed land deal, and thus “a villain without principles, very artful and could be very troublesome.” As though conscious that he was serving his own purposes, Wilkinson stressed his zeal and loyalty to Spain’s interest. In one passage, he suggested openly switching sides and asked Madrid to grant him “a military commission, because I know that the force of my genius inclines to the science of war, and that in this capacity I can afford the strongest proofs of fidelity, loyalty, and zeal.”