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TWO DANGEROUS EVENTS PENETRATE a spy’s cocoon of secrecy, the transmission of information and the receipt of payment. For Wilkinson, the problem of getting his hands on Carondelet’s munificent reward without arousing suspicion required particular care. In a letter to the governor written just before Fallen Timbers, he had recommended that the money be entrusted to two messengers. Captain Joseph Collins, a reliable but unimaginative officer from his staff, would travel to New Orleans posing as a trader in flour, and he was to be accompanied by Henry Owens, a quick-witted but unsuccessful Kentucky settler. Both understood the money to be payment for Wilkinson’s tobacco sales and, since it was in silver dollars, it needed to be shipped in utmost secrecy. When they arrived in New Orleans, Carondelet divided the twelve thousand dollars between them and sent each north by a different route.

On August 6, while the Legion was still struggling through the morasses and stinging nettles, Owens left New Orleans heading up the Mississippi with $6,000 in coins packed into three barrels of sugar in the hold of a Spanish galley. Two weeks later, on the very day that Fallen Timbers was fought, Collins took passage in a ship sailing for Charleston, carrying $6,333, a sum sufficient to pay all the expenses allegedly incurred by Wilkinson in checkmating the expedition planned by George Rogers Clark. The knowledge that this gigantic windfall was on its way and had somehow to be smuggled past watchful eyes and wagging tongues that might alert Wayne no doubt contributed to the stress that marked Wilkinson’s increasingly strident attacks on the commander.

By October, Owens had reached the Spanish fort of New Madrid. The most difficult part of the transfer, taking the money up the Ohio and past U.S. strongpoints such as Fort Massac, now began. New Madrid’s commander, Tomás Portell, and François Langlois, a militia officer in charge of galleys on the river, discussed with Owens the best way to escape detection. Langlois proposed that Owens travel openly as a trader with a new crew recruited in the settlement, but was overruled by the other two, who preferred secrecy. Accordingly in November, Langlois took a nervous Owens and his three precious casks in a Spanish boat to the mouth of the Ohio, where they transferred to a small canoe manned by six Spanish sailors. At the last moment, Langlois thought it too dangerous to allow so much money to be transported in an open boat and took the barrels back, but Owens, who stood to make about $600 from the delivery, insisted on taking the dollars in the canoe before winter came and ice blocked the river.

This very public quarrel destroyed any semblance of secrecy. Within days, Wilkinson’s courier was dead, murdered by one of the paddlers in his canoe, a Spaniard named Vexerano, for the silver dollars inside the barrels. The crime was soon known on the Spanish side because one of the paddlers hurried back to New Madrid to alert Portell, but four others including Vexerano continued up the Ohio before splitting the cash and scattering into the Kentucky countryside. Unable to speak English, and in possession of large sums of money, they immediately aroused suspicions in the closely knit rural communities they traveled through.

For Wilkinson, waiting in Fort Washington for the money, Owens’s murder was the worst possible outcome. Not only was he deprived of cash he needed to pay his debts, but somewhere at large were four criminals who could provide tangible evidence that he was being paid by Spain. In December, three of the boatmen were arrested in Kentucky and brought before the federal judge in Frankfort. Fortunately this happened to be Harry Innes, who was almost as deep in the conspiracy as his client. He immediately informed Wilkinson that the three men were under arrest and had them shipped in irons to Fort Washington in Cincinnati.

Yet with Captain Pierce, the fort’s commander, on the lookout for foreign agents, Wilkinson could not afford to keep the three Spaniards there. On the grounds that Spain had jurisdiction over them, he ordered them to be taken down to the fort at New Madrid on December 29, escorted by Lieutenant Aaron Gregg and a Kentucky lawyer, Charles Smith. But the boat got no farther than Fort Massac, where Major Doyle, equally suspicious of strange movements on the river, had lookouts posted. The boat was spotted as it tried to slip past under cover of night, and at musket point it was ordered to shore, where those on board were brought in for questioning. Smith produced a written order from Wilkinson giving them free passage, but Doyle decided that because the three prisoners had committed their crime on U.S. soil, they could proceed no farther until he had questioned them himself.

Had anyone in Fort Massac spoken Spanish, Wilkinson’s career would have been ended. Doyle was Wayne’s man, and the murderers’ evidence would have given the general incontrovertible information linking his enemy to Spain. But for the second time, luck went Wilkinson’s way. The fort was manned by monoglot English speakers, and Doyle had to send to New Madrid for an interpreter.

In January 1795, Thomas Power, a bilingual Irishman who acted as Carondelet’s confidential messenger, arrived from New Madrid to translate. Intimately aware of the sensitive information the prisoners possessed, Power carefully censored any reference to Owens’s mission from the answers they gave to Doyle’s questions. Although unaware of the prize he held, Doyle remained sufficiently suspicious to send them downriver to Louisville for trial. Still acting as interpreter, Power went with them and again doctored their replies to court officials there because, as he later admitted, “it was the wish of the Spanish officers to have the men delivered to them rather than tried in the territory of the United States, and such a wish arose from a fear of divulging the secret of Owens’ mission.” By this time the prisoners knew their lines, and all denied being concerned in the murder. Frustrated, the Louisville court at length remanded the prisoners to their starting point, Judge Innes in Frankfort.

An increasingly anxious Wilkinson let his old friend know that, to buy the prisoners’ silence, he was ready “to pay the three two hundred dollars if they should not be compensated by the Spanish government.” But Innes found a cheaper solution. In the weeks since he’d first questioned them no new evidence had come forward, and in March he discreetly concluded that the lack of witnesses made a trial impossible, and that the prisoners should be set free on condition they left Kentucky at once. In June 1795 the unfortunate Major Doyle was summoned upriver to Fort Washington, where he paid the price for his initiative by being put under arrest for disobeying Wilkinson’s orders to let the men through. At about the same time, Vexerano was arrested in New Madrid, and his execution in New Orleans later that year removed the last threat to Wilkinson of exposure by Owens’s murderers.

Nevertheless, suspicion still hung round him—the angry Doyle blamed “a base and ambitious faction” for his arrest—and Wilkinson’s money had gone missing. Most damagingly as it turned out, the distraction had prevented him from feeding anti-Wayne propaganda either to the press or to Congress during the debates on the future size of the army. Although the House voted to reduce its numbers and, as a result, to abolish the post of major general, popular opinion was swinging in favor of the Legion and its commander as the effects of Fallen Timbers made themselves felt.

At the end of 1794, the Legion had marched into the Indiana prairie, the breadbasket of many of the nations that made up the western confederation, and not only destroyed most of their farmland, but erected the looming edifice of Fort Wayne. Before the winter was over, hunger drove the confederation’s sachems and war leaders to begin negotiating a peace agreement. Whatever the ideological argument about the merits of a regular army and a militia, it was becoming obvious that, as Cornelius Sedam, a straight-talking New Jersey soldier, put it, “by many Genl. Wayne has been Sen-sured . . . [but] Saying here and Saying there has no Effect. He has Done the Business and that Settles the Dispute.” On March 3 the Senate agreed, and its vote guaranteed the Legion’s existence for another three years. Nailing Wilkinson’s ambition into its coffin, the Senate also voted to make its commander a major general.