General James Wilkinson, the Spanish Spy Who was a Senior Officer in the U.S. Army During Four Presidential Administrations

To celebrate National Library Week during this time of social distancing, we encourage you to explore the collections of the Library of Congress online. One of the great things about exploring the collections of the Library of Congress is its ability to surprise you. In that spirit, I wanted to share something I came across in the digital collections of our Manuscripts Division. You are looking at a drawing of a rock carving that was sent to Thomas Jefferson by General James Wilkinson, who served as a senior officer in the United States Army under Presidents Washington, Adams, Jefferson, and Madison. What is so interesting about finding an item written by Wilkinson is that he was later revealed to be Agent 13, a spy selling secrets of the United States to the Spanish crown.

President Theodore Roosevelt later described Wilkinson as follows: “In all our history, there has been no more despicable character.” Wilkinson was under suspicion of being a “Spanish pensioner” throughout his life. Born in Charles County, Maryland, Wilkinson trained as a medical doctor, but soon found his calling as a soldier during the Revolutionary War.

Chronically short of money due to his lavish spending, Wilkinson sought to supplement his income by becoming a spy for the Spanish. Wilkinson’s early efforts focused on an attempt to separate Kentucky and Tennessee from the United States to deliver them to Spain. Wilkinson also informed the Spanish about the Lewis and Clark expedition (Linklater, p. 208). Though the Spanish did not manage to locate them, one can imagine that if the Spanish did catch up with them, Lewis and Clark would have simply disappeared. Wilkinson’s information also helped the Spanish delay the annexation of Texas by the United States (Linklater, p. 236).

Wilkinson was very nearly caught on two occasions. In order to pay Wilkinson, the Spanish floated coins hidden in coffee and sugar barrels up the Mississippi and Ohio Rivers (Linklater, p. 155). The Spanish-speaking boatmen figured out that there were coins hidden in the barrels, murdered the courier, and spread out across the Kentucky countryside. After they were apprehended, they were brought before a magistrate in Frankfort, Kentucky. The magistrate sent for an interpreter named Thomas Power, who unfortunately for the boatmen, was also a Spanish spy (Linklater, p. 146). When the magistrate asked the boatmen to account for themselves, they responded by explaining to Power that the coins were a payment for Wilkinson from the Spanish crown. Power “interpreted” their testimony by explaining to the magistrate that the men stated they had committed a cold blooded murder and were motivated by greed. As a result, one of the boatmen was hung, and Wilkinson was spared.

Wilkinson was also nearly identified as a key participant in the Aaron Burr conspiracy. Burr’s precise objective is still unclear, ranging from an attempt to separate the West from the United States to a plot to depose President Jefferson, but what is clear is that Wilkinson became nervous that Burr’s conspiracy would fail, and sought to minimize the appearance of his involvement and portray himself as a savior of the Republic to Jefferson. In order to minimize the appearance of his own involvement in the conspiracy, Wilkinson doctored a ciphered letter that implicated Burr and then turned that letter over to the Jefferson administration. Wilkinson’s sanctimonious attitude at Burr’s trial rankled one observer who described him, based on his considerable girth and garish uniform of his own design, as a “mammoth of iniquity.”

Despite widespread suspicions about his loyalties, how did Wilkinson retain his position? First, Wilkinson was an effective military commander, but also federal administrations in the early United States feared that if they did not command the loyalty of the army, it could threaten to depose them. Wilkinson’s ability to control the army, and maintain its loyalty to democratic, civilian institutions, made him a valuable asset despite the cloud of suspicion that hovered above him (Linklater, p. 195).

One such demonstration of Wilkinson’s loyalty to the authority of the civilian government was illustrated by banning the queue hairstyle in the army. This hairstyle (which looks something like a braided pig tail that is greased with flour and lard, if you are looking for a new look) was popular among members of the army as a signal that they were warriors. It also become associated as a sign of partisan loyalty to the Federalists. After Jefferson took office, Wilkinson sought to ingratiate himself by issuing a controversial order that banned the queue in the army (Wilkinson, p. 501). This was met with resistance by a Revolutionary Army hero named Colonel Thomas Butler who resisted the order to the point of facing a court martial (Wilkinson, p. 501). While he awaited punishment for his defiance, Butler died of yellow fever in New Orleans (Wilkinson, p. 512). Supposedly, Butler wrote in his will: “Bore a hole through the bottom of my coffin, right under my head, and let my queue hang through it, that the damned old rascal will see that, even when dead, I refuse to obey his (Wilkinson’s) orders” (Linklater, p. 355).

In 1854, long after Wilkinson’s death,  letters were discovered in a Spanish archive that confirmed Wilkinson had indeed been a spy operating on behalf of the Spanish crown, leading to the description of him as an “Artist in Treason.”

A subtle reminder of Wilkinson’s questionable legacy can still be observed while driving through Frankfort, the capital of Kentucky, where Wilkinson laid out the grid for many of the early streets. Wilkinson brazenly named one of those streets for a Spanish governor who was paying him, Mero Street (the correct spelling of the governor’s name is Miro), which intersects with Wilkinson Boulevard.

Sources:

Andro Linklater. “An Artist in Treason” (2009).

James Wilkinson. Colonel Thomas Butler and General Wilkinson’s “Roundhead Order.” The Pennsylvania Magazine of History and Biography Vol. 17, No. 4 (1893), pp. 501-512.