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Our Rich History: James Wilkinson, Kentucky politician, American general — and Spanish spy

By Steve Preston
Special to NKyTribune

 “In all our history, there is no more despicable character.” Theodore Roosevelt

While the formative years of the Ohio Valley and Northern Kentucky were often filled with a rogue’s gallery of characters such as Lewis Wetzel, Simon Girty, and Aaron Burr, one character stands out from all the rest, James Wilkinson.

A somewhat competent officer of the American Revolution, Wilkinson would manage to charm or destroy those who presented a chance of advancement for him. While this may seem petty and obviously self-serving, it pales to what Wilkinson did while living in the Tristate area.

James Wilkinson was born on March 24, 1757. He spent his childhood in Calvert County, Maryland. Early in his youth, Wilkinson enjoyed a privileged upbringing on his family’s property known as Stoakley Manor. Eventually, his father sold the property to cover family debts. Despite this, Wilkinson still managed to begin studying medicine at the University of Pennsylvania. Feeling himself already qualified, the 17-year-old Wilkinson dropped out of medical school after about a year and a half of studies. He soon found he did not particularly enjoy being a doctor. The outbreak of the American Revolution provided him with a new profession, soldier.

The shots fired at Lexington and Concord drew Wilkinson into the military world. He headed towards Boston. Eager to join up, Wilkinson attached himself to a Pennsylvania rifle battalion. He was commissioned a Captain due to his education. After the British left Boston, he was an aide to Nathaniel Greene. He also served as an aide to Benedict Arnold and Horatio Gates.

James Wilkinson (Wikipedia)

In a harbinger of behavior to come, General Gates gave Wilkinson the honor of delivering the news of the victory at Saratoga to Congress. Not only did Wilkinson keep Congress waiting while attending to personal matters, when he finally did appear, he inflated his own role in the victory. His disingenuous actions paid off, though. The 20-year-old Wilkinson was given the brevet rank of Brigadier General.

A drunk Wilkinson later inadvertently exposed the Conway Cabal attempt to replace General Washington. He did this at the expense of his patron, Horatio Gates. Because of this conflict, he was forced to resign as the newly appointed Secretary to the Board of War. His next military appointment was that of Clothier-General of the Army. He soon resigned due to “lack of aptitude” for the job.

The end of the Revolutionary War found Wilkinson, his wife Nancy, and their year-old child John in Kentucky. Relying on family and friends, James bought land at the Falls of the Ohio (Louisville) and also near the Licking River. He set up a store in Lexington. The newly arrived Wilkinson enjoyed a very welcoming atmosphere due to his rank, service in the war and his social connections back East. He soon found himself immersed in Kentucky politics. Wilkinson became a supporter of Kentucky’s independence from Virginia.

Wilkinson also used his charm, personality, and flattery to gain an audience in Spanish New Orleans on behalf of Kentucky merchants. But the ever-ambitious Wilkinson had a darker ulterior motive. Aside from gaining a monopoly on Kentucky trade with Spanish New Orleans, Wilkinson talked to the Spanish Governor, Esteban Rodriguez Miró, about Kentucky seceding and becoming part of Spanish North America. He said he was speaking on behalf of “notable Kentuckians” about becoming “vassals” in the Spanish Kingdom. All Spain had to do was allow access to free trade on the Mississippi River by Kentucky citizens. If Spain wasn’t interested, they’d go to Britain. This was the beginning of what became known as the “Spanish Conspiracy.” His correspondences would be in code. The Spanish would use their “cypher” number 13 to decode, thereby giving Wilkinson his spy name, Agent 13. He refused to be called anything else by his Spanish handlers.

This also became the beginning of Wilkinson’s sedition and the genesis of a lengthy professional career as a traitor to the United States. If there was any doubt left about his allegiance, that was swiftly put to rest by Wilkinson signing a Spanish document declaring his loyalty to the Spanish Crown.

Wilkinson was welcomed back in Kentucky as a hero for his efforts. He was selected to represent Fayette County at the Danville Convention where the fate of Kentucky would be settled, to become a new state or remain part of Virginia. Wilkinson was anti-constitution and anti-statehood. While this may seem radical, at the time many settlers west of the Appalachian Mountains felt that the politicians back east only had the interests of the 13 new states in mind as they built a government. But there was a big difference in Wilkinson and his colleagues, who envisioned outright secession and a running to Spanish control. Wilkinson would have to put his espionage on the backburner as an outbreak of hostilities between settlers and Native American would take precedent.

Seeking a way back into the army, Wilkinson led a regiment of Kentucky volunteers to raid Indian villages on the Wabash and Eel Rivers in present-day Indiana. While Wilkinson was raiding in the West, General Arthur St. Clair was marching America’s army up to the Wabash River in present-day Ohio. His foray to chastise the Indians met with a massacre. Surprised, the inexperienced troops were no match for the warriors they fought. The remnants of the army limped back to Cincinnati and Fort Washington.

As a result of these raids, Wilkinson was able to reenter the United States Army as a Lieutenant Colonel. And as a result of St. Clair’s disastrous defeat where he incurred over 80% casualties in America’s fledgling army, President Washington was looking for a new General. The two obvious candidates to replace St. Clair were Wilkinson and Anthony Wayne. Washington and his advisors weighed the pros and cons of each. Wayne could be rash in his decisions, vain, and open to flattery. Wilkinson was thought to be inexperienced, pompous, and to have “many unapprovable points in his character.” Whispers of his dealings with the Spanish may have been one of those points. As a result, Wayne was made commander, and Wilkinson was promoted to Brigadier-General with the promise of being second-in-command to Wayne. A Spanish spy now held the number two post in the United States Army.

James Wilkinson could be an effective military officer. His organizational skills were well developed. Instead of putting them to use improving the army, he instead used his skills to undermine Anthony Wayne. Wilkinson continued to pass along troop movements and military strategy to his Spanish handlers in New Orleans. General of the Army Anthony Wayne finally became aware of the scale and the magnitude of Wilkinson’s betrayals but died before he could move forward with outing him. With Wayne’s death, James Wilkinson became Commander of the United States Army.

With this newfound power, Wilkinson lessened his communications with Spain and instead supplemented his income by grafting traders and sutlers, who sold goods to soldiers in and around military forts like Fort Washington and other fortifications in the Northwest Territory. Financial solvency was always the impetus for his betrayals. His extravagant living made his spying just a means to an end. Bribes and grafts worked just as well as Spanish Reales and were safer.

Wilkinson, in 1794, had narrowly avoided exposure when a large payment from his Spanish handlers was sent North in the form of coins stored in barrels. The Spanish oarsmen in the boat carrying the money, which was stashed in sugar barrels, robbed and killed Wilkinson’s American contact. Wilkinson’s luck held since the oarsmen only spoke Spanish, and the only interpreter was also in the pay of the Spanish government. When translating for the courts, the interpreter strategically left out parts of the incident that incriminated Wilkinson.

Ft. Washington, Cincinnati. (Courtesy of Library of Congress)

The elitist Wilkinson considered the officers of Fort Washington mostly beneath him socially, calling many of them “drunkards” and “fools.” Despite his hidden treacherous activities and general contempt for his officers, Wilkinson got along well with most of the soldiers at Fort Washington, as well as the citizenry of Cincinnati and Northern Kentucky. Wilkinson enjoyed an extravagant lifestyle for what was then the frontier. He held lively parties and balls where he would wear his finest uniform and be a gracious host. He often entertained guests on a barge he had constructed on the Ohio River. Musicians would play, as the guests enjoyed drinks amidst the sun going down on the Ohio. His wife, Nancy Biddle Wilkinson, proved even more universally popular than Wilkinson himself. Her charm, pleasantness and her femininity made her a favorite of officers, enlisted men, and civilians alike.

While commander of Fort Washington, Wilkinson had the best accommodations and largest garden inside the garrison. His favorite locale, however, was Fort Hamilton on the Great Miami River in present-day Hamilton, Ohio. Here, he enjoyed a large officer’s quarters with a veranda overlooking the river. Away from the hustle and bustle of Cincinnati, he was free to relax and scheme unfettered. By 1799 and with the responsibility that comes with being the General of the Army, Wilkinson spent most of his time back East or visiting other military garrisons that had moved the frontier further west. Fort Washington and the line of forts up Western Ohio were no longer needed. In fact, James Wilkinson was the one who penned the September 6, 1799 letter to Alexander Hamilton, recommending the closure of the Ohio forts.

Being away from Cincinnati certainly did not diminish his penchant for intrigue or self-promotion. In 1801, near the confluence of the Ohio River and the Mississippi Rivers, Wilkinson had built a military installation he named “Cantonment Wilkinson.” It was built to strategically keep an eye on the British, French, and Spanish that still had a foothold and were a threat in the area. Some speculate it was built to revive parts of the “Spanish Conspiracy.”

Wilkinson continued to inform the Spanish of military movements. After the Louisiana Purchase, Wilkinson made the Spanish officials aware of the planned exploration by Lewis and Clark. He advised the Spanish to pursue and arrest them and the rest of the Corps of Discovery. A rightly wary Lewis and Clark skirted the far side of the river as they descended to St. Louis to embark on their great exploration of the West.

In 1805, President Thomas Jefferson appointed James Wilkinson as Governor of the Louisiana Territory. This took him permanently away from the Cincinnati/Northern Kentucky area. It did not, however, stop the intrigue. He was involved in Burr’s plot to carve out a new country in the middle of the West, including Ohio, Kentucky, and parts of Mexico. When Burr’s plan was about to be implemented and Wilkinson’s role in it defined, Wilkinson sent letters back East, blowing the whistle on the affair. Since he was implicated as well, he was also put on trial but was acquitted. Despite this, more people became aware of his behavior. The foreman of the jury that acquitted him, John Randolph, stated he was “the only man I ever saw who was villain from the bark to the core.”

Wilkinson’s last attempt at military glory was during the War of 1812. At the Battle of Crysler’s Farm near Morrisburg, Ontario, Wilkinson’s force of around 4,000 men was soundly defeated by less than 1,000 British and Canadians. This debacle led to his third court-martial. While awaiting his trial, he tried to gain back some military standing by taking 4,000 men to attack 80 men guarding the Montreal Road at the Lacolle River. This proved another disaster for Wilkinson. His forces were repulsed after the British reinforced the position. His court-martial ended, and he was once again cleared of any wrongdoing.

Through four presidents, three court-martials and four congressional investigations, Wilkinson had managed to emerge unscathed. Robert Leckie said of Wilkinson: “He never won a battle or lost a court-martial.” What he couldn’t escape was old age and the military cuts of a peacetime army. James Wilkinson was “retired” by the United States Government in the military draw-down immediately after the conclusion of the War of 1812. He settled on a plantation in the South but was financially unable to keep it. He moved to Mexico City, Mexico. His dream of owning large tracts of land near Galveston never came to fruition. He died an expatriate American on December 28, 1825 at the age of 68.

Steve Preston is the Education Director and a Curator of History at Heritage Village Museum. He received his MA in Public History from Northern Kentucky University.

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  1. Glenn S. Oncay says:

    Fascinating Story; Thank you
    I am in search of the names of the Spanish oarsman that were tried before a court with results of one being hanged. Please provide any references to this event and any holdings and access to find this information.
    Thank you

  2. Lisa Livingston says:

    Glenn , I don’t have the answer you are in search of but I believe I may know you !
    I think we attended the same elementary school . I have a friend that is currently at a library doing some
    genealogy research, and she loves this type of a challenge. I would be happy to ask for her assistance.
    As soon as she returns I will pass your information on to her . I use to live in central Louisiana as a child , I’m from there.

Reply to Lisa Livingston Cancel Reply