Most Americans have heard of Benedict Arnold who was a traitor to the American Revolution. Arnold was found out before he could turn over the fort at West Point to the British and escaped before he could be detained. Arnold was given a commission of general in the British army, and after they lost the war, he was exiled to England. Like Arnold, James Wilkinson was an officer in the Continental Army. After the war Wilkinson sold out to the Spanish Empire and led a double life for about 40 years. He actually did damage to the young USA but avoided exposure and execution due to excellent spy tradecraft and amazing luck. Wilkinson was a traitor against his own country and in my “Charlie Brown” definition was assuredly an American Rogue of the worst kind.
James Wilkinson was born in 1757 in Charles County, Maryland into a plantation family. His family was well-to-do, but not in the same social and financial league as the Virginia Washingtons, Jeffersons, and others. By 19 years old, Wilkinson was a junior officer in the Continental Army and played an important part in the victory at Saratoga. General Horatio Gates was the American commander at that battle and Gates chose Wilkinson to negotiate the terms of surrender of British General Burgoyne’s army of 6,000 men. He was picked for this job because he was ambitious, very charismatic, had strong persuasive powers, was charming, and very self-confident. (Great traits for a spy !!)
Wilkinson impressed his superiors, including Gates, Benedict Arnold and Nathaniel Greene, and at age 20, he became the youngest American-born general in the Army. Before the war ended, he had betrayed them all. He was also engaged in a bitter personal rivalry with General “Mad” Anthony Wayne until 1796 when Wayne died. In 1778, Wilkinson became involved in the so-called “Conway Cabal”, a plot to replace General Washington. Wilkinson eventually ratted out General Gates’ connection to the plot while trying to downplay his own involvement; however, he still was forced to resign. Despite his involvement in the plot, the following year, with Washington’s approval, Wilkinson was appointed Clothier General. In 1781 he was forced out again amid allegations of corruption.
At this point, I should point out that after the Constitution was ratified, the new nation was fragile with no guarantee that it would survive, much less expand. Our founders now had to make it work, and there was not universal agreement on how to do that. There was considerable dissention at all levels, and failure threatened every political choice. Also, there were powerful and hostile foreign forces on the North American continent – Britain in Canada, France in Louisiana, and Spain in Florida and on the western border. The Spanish empire was by far the largest and was active using American traitors to help oppose any expansion of the new country.
In the USA, discussions were already in progress about the admission of Kentucky (part of Virginia) into the union. This was not as simple as we have been led to believe because powerful and conflicting internal and foreign interests were involved. At the same time the new government was struggling with the question of the place of a “standing army” in a democratic state.
With all this as backdrop, in 1784 Wilkinson set out for Kentucky to make his fortune. Spain controlled traffic on the Mississippi River where they bordered American territory. The Spanish severely limited American access to markets in New Orleans by charging high tariffs on the river.
Wilkinson wrote a memo to the Spanish authorities hoping to obtain a monopoly on commercial movement on the Mississippi. More importantly, he became a traitor by signing a document “transferring allegiance from the United States to his Catholic Majesty”. At this point Wilkinson became a “pensioned” spy for the Spanish Crown. This began a life of duplicity and treason by a man that was known to his handlers as “Agent 13”. He was probably the most successful spy in American history.
While in Kentucky, Wilkinson engaged in efforts to persuade others to favor not only separation from Virginia, but from the new United States itself. Leaving Virginia had been a popular position in Kentucky under the Articles of Confederation. At that time the Spanish were forceably controlling commercial traffic on the Mississippi River to New Orleans, and the weak government in Philadelphia had been unable to correct the problem. What will surprise many is that support for seceding from the new Union was very popular too, and these opinions were being pushed by the traitor Wilkinson and other Spanish agents. They enflamed the situation by telling Kentuckians they would get a better deal from the Spanish, which was what many already believed. Ultimately, Kentucky was admitted to the Union under the new Constitution in 1792 after 10 years of effort by loyal Kentuckians.
By 1791, Wilkinson was back in the American army while still serving his Spanish masters. This made him privy to information that was even more valuable to the Spanish for use against the Americans. In five short years Wilkinson become the nation’s ranking Army officer, which was similar to today’s Chairman of the Joint Chiefs. Obviously, this gave him access to even more sensitive information and enlarged his power base.
Wilkinson managed to make himself seem indispensable during the presidencies of Washington, Adams, Jefferson, and Madison even though there were strong rumors of his treachery. This inability to consider the widely accepted opinion that Wilkinson was a servant of Spain allowed him to regularly feed valuable information to his Spanish handlers. For example, he reported that President Jefferson was planning to dispatch Meriwether Lewis and William Clark on an expedition into the Louisiana Territory through lands still claimed by Spain. He urged the 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.” The Spanish followed his advice and it was only luck that prevented their forces from intercepting the Americans. Had they succeeded, American history would have turned out very differently.
Wilkinson also recommended that the Spanish build strong defensive lines to prevent American westward expansion, another idea that the Spanish acted on. He submitted a paper outlining steps the Spanish could take to oppose American westward expansion. Apparently unaware of the extent of Wilkinson’s treachery, and at the suggestion of Aaron Burr, Jefferson rewarded him for other services by appointing him Governor of Louisiana. A position he held in 1805 and 1806. This was like putting the fox in the henhouse !!
The tension between the USA and Spain had increased considerably following the American purchase of the Louisiana Territory from France in 1803. The border between Spanish Texas and the western edge of Louisiana was in dispute and was threatening to erupt into war. The Spanish reinforced the area with more than 1,000 troops, and occupied area that the USA claimed. President Jefferson ordered General Wilkinson to move to counteract the Spanish. Wilkinson replied that with his available forces he would “drive our opponents before me”. Militia forces in Kentucky and Tennessee under Andrew Jackson and John Adair were also very anxious to join the fight against the hated Spanish if hostilities began.
It was during this period that Aaron Burr twice traveled to the west, secretly recruiting officers for an independent western American government. Such a move would have confirmed Spain’s worst fears about the security of Mexico. Burr envisioned occupying New Orleans and taking Spanish Texas. Wilkinson was in cahoots with Burr initially, and if he had moved against the Spanish on the border, New Orleans would have been unprotected and easy pickings for Burr. This situation changed when Wilkinson decided Burr was destined to fail and reported the conspiracy to President Jefferson. This revelation also exposed his collusion with Burr. In the treason trial that followed, Chief Justice John Marshall rightfully ruled strictly in line with the Constitution that conspiracy was not treason and Wilkinson and Burr both walked.
This was the beginning of the end for Wilkinson, although he continued to lead American troops during the War of 1812. He occupied Mobile in Spanish West Florida and conducted two operations, which were unsuccessful, against Canada. The president eventually lost faith in Wilkinson and sacked him. Wilkinson then migrated to the newly established, but short-lived Mexican Empire. Once in Mexico, he tried to convince the Mexican Government to split Mexican Texas into two parts and let him govern the eastern half. The Mexicans wisely chose not to do this. Wilkinson died and was buried in Mexico in 1825.
Proof of Wilkinson’s treachery did not surface until 1854. Further research was done in the 20th century, which exposed the extent of his spying. Since many contemporaries suspected that he was on the Spanish payroll, it seems impossible that he could have been so successful for about 40 years without being found out and hanged. He was always fearful of exposure, and faced four or five public inquiries, two or three court martials, and each time was found not guilty.
Wilkinson’s success was a combination of many factors starting with his charisma. It has been noted that he was very smart, very persuasive, charming, and super confident. He also impressed powerful people, even though he eventually betrayed most of them. His spy tradecraft was impressive. He rarely met with his handlers, and communicated with them only in code–a code that to this day has not been broken. He was paid in American silver dollars, which were easily laundered through banks and real estate deals. The coins were often smuggled to him from New Orleans in small wooden kegs designed to transport sugar and coffee. These kegs were weighed carefully to reflect the proper weight of the supposed contents. He also had forged documents that would back up his cover stories for the influx of cash.
Luck was certainly a major factor in his success. One example of luck was when his messenger transporting about $ 3,000.00 was murdered by his boatmen. The murderers then went on a spending spree, but were caught and held for trial, which meant that Wilkinson was likely to be exposed by their testimony. However, the murderers spoke no English and the court interpreter was another American traitor working for Spain. He, of course, covered for Wilkinson. The Spanish had a surprisingly large spy network in the USA at the time.
Another very important factor was that Wilkinson was an effective military commander who served the nation even while he betrayed it. He provided America with military stability and some victories. The presidents he served looked at results rather than unproved evidence and used him where they believed he could be the most valuable. He usually maintained good relations with the presidents, especially Jefferson, which is where it counted.
One reason early presidents counted on him was the perceived hazard of a standing military force in a democratic nation. Wilkinson agreed through practice that such a force should be fairly small with officers loyal to the American Republic and the people rather than to a person or political group. All other post-revolutionary states in the hemisphere did not confront this situation, and all eventually suffered military coups. Our founders were correct to be concerned and took the proper steps to give us a military that has remained under civilian control for almost 300 years. Historically, this has been one of our strengths by assuring and protecting a stable system of government.
The establishment of our Republic and all the development that followed, was put in serious jeopardy by the treachery 0f Wilkinson. We should always be vigilant against subversion from within. In my opinion, turning on America is the worst crime that can be committed, and all traitors should be hanged.