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James Wilkinson: The Man Who Double-Crossed the Founders of America

The notorious statesman's ability to get out of tight pinches while benefitting himself is beyond compare.

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  • Photo Credit: Wikimedia Commons

Being appointed senior officer of the U.S. Army, territorial governor of Louisiana and major-general of the Continental Army (aged only 20, with no combat experience) would normally be hallmarks of a great American.

James Wilkinson, however, wasn’t a great American. Wilkinson was a crook, traitor, liar, master manipulator, social climber and egotist, aggressive toward anyone questioning his motives or actions. Accusations didn’t offend a sense of general principle (he had none), but because he had so much to hide. Attack was his favorite defense.

Joining the Continental Army in 1775 only a month after its formation, Wilkinson’s rise owed more to understanding, flattering, and manipulating his superiors than to any military talent. Commissioned a captain, he didn’t stay one for long. He served under Benedict Arnold in the failed Canada expedition before becoming aide to General Horatio Gates in August 1776.

Related: "Villainous Perfidy": Benedict Arnold's Betrayal of George Washington 

Wilkinson’s talent for fickleness soon showed itself. Arriving late with the dispatches that announced victory at Saratoga (having put personal matters before military duty), Wilkinson betrayed Arnold. He credited Gates with winning Saratoga, embellished his own role for maximum effect, and abandoned former mentor Arnold to impress Gates. That didn’t win him many friends–nor did being breveted brigadier-general over more deserving officers. At only 20 with nearly no combat experience to speak of, he’d already risen higher than he deserved. The irony of betraying Arnold probably amused Wilkinson no end. 

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  • Horatio Gates (left) and Aaron Burr (right)

    Photo Credit: Wikimedia Commons

His ties to Gates didn’t last. Wilkinson accidentally betrayed the ‘Conway Cabal,’ a loose group of officers plotting to replace Commander-in-Chief George Washington with Gates. Gates was furious, especially when Wilkinson tried to blame others. Their partnership ended acrimoniously as Wilkinson resigned. Only a year later, Wilkinson was appointed clothier-general in 1779, but he resigned again in 1781, officially because he lacked aptitude. Unofficially, Wilkinson found the work tiresome and the pay insufficient. 

Wilkinson then became brigadier of the Pennsylvania militia, while also serving two terms in the State Assembly. Moving to Kentucky in 1784 (at the time, part of present-day Virginia) he also began treasonously serving Spain. Rivalry between colonial Spain and Washington was heated. Wilkinson, ever the opportunist, happily served both.

Related: The Culper Ring: The Revolutionary Spies Who Helped Win the War 

In April 1787, he made a deal with Esteban Rodriguez Miró, Spanish governor of Louisiana (then a Spanish possession). In exchange for Kentucky’s exclusive trading rights with New Orleans, then a Spanish colony, Wilkinson covertly promoted Spanish interests and sold American secrets. Signing an oath of allegiance to Spain, Wilkinson secretly became known as ‘Agent 13.’

Returning to Kentucky in 1788, Wilkinson involved himself in local politics. He advocated Kentucky seek independence from Virginia and ally themselves with Spain, effectively removing Kentucky from the Union. Kentucky joining the United States was only the second option. By any reasonable definition, this was the highest form of treason.

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Another deal with Miró beckoned. Wilkinson wanted 60,000 acres of land along the Yazoo River near present-day Vicksburg for services rendered, but also a hideout if his Kentucky scheme failed. Wilkinson also wanted annual pensions for himself and other prominent Kentuckians. His Spanish paymasters, losing confidence in Agent 13, refused. Only Wilkinson got his pension. Miró was also forbidden to finance Kentuckian revolution. 

Wilkinson rejoined the military. After leading Kentucky volunteers against Native Americans, he became Lieutenant Colonel of the 2nd U.S. Infantry. Again, he rose quickly. Washington appointed Anthony Wayne as Senior Officer of the U.S. Army, making Wilkinson a Brigadier to salve his ego. The Wayne-Wilkinson feud became bitter and personal. 

Related: 7 of the Best American History Books 

Wayne investigated Wilkinson’s Spanish links and even began the process to have him court-martialed. When Wayne died in December 1796, the threat seemed to die with him. Despite growing suspicions, Wilkinson still replaced the deceased Wayne as senior officer. He now ran the army he was betraying until transferring to Southern Command.

Wilkinson returned as senior officer (and his treason with Spain) in June 1800, remaining in that post until January 1812. Appointed the first territorial governor of Louisiana in 1805, Wilkinson’s treachery continued as he informed Spain of the Lewis and Clark expedition, even suggesting they be hunted down by Spanish cavalry. Fortunately for Lewis and Clark, Spanish cavalry never found them.  

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  • James Wilkinson

    Photo Credit: Wikimedia Commons

Implicated in former Vice President Aaron Burr’s conspiracy to establish an independent nation made up of western U.S. States and territories, Wilkinson entirely blamed Burr: producing a doctored letter purportedly from Burr but in Wilkinson’s handwriting. The Grand Jury ruled Burr had intended treason but committed no overt act of war. Concealing this treasonous plan almost undid Wilkinson too, but a lack of hard evidence prevented his indictment. Ironically, having seen through Wilkinson’s subterfuge, jury foreman John Randolph described him as “a mammoth of iniquity… The only man that I ever saw who was from the bark to the very core a villain.”

Burr resembled a victim more than a conspirator, later escaping to Europe. Wilkinson, perceived as exactly the opposite, came off very badly. Things were also getting considerably worse for him. 

Other heavy blows quickly followed. Wilkinson was removed as Territorial Governor in 1805 accused of heavy-handed administration and abuse of power. Two Congressional inquiries, a military Court of Inquiry in 1809 and court-martial in 1811 further diminished his standing. Wilkinson’s reputation was permanently tarnished. Historian Robert Leckie described him as “a general who never won a battle or lost a court-martial”, while historian Frederick Turner was less kind: “the most consummate artist in treason that the nation ever possessed”.

Related: Lysander Spooner: The Man Who Took on the U.S. Postal Service—and Won 

Wilkinson’s career ended sourly. Two failed campaigns in the War of 1812 saw him investigated again, this time for incompetence. Wilkinson was cleared yet again but discharged on June 15, 1815. He went to Mexico in 1822 hoping to become advisor to Emperor Agustin, but Agustin abdicated in 1823. Wilkinson himself died on December 28, 1825 in Mexico City and was not unmasked as one of America’s worst traitors until 1854 by historian Charles Gayarré.

Some historians argue to this day about Wilkinson’s true motives, with one faction pointing out the futility of his attempts to separate Kentucky from the burgeoning Union as a sign that he wasn’t truly trying to betray the United States. However, the payments from Spain that went on for years, Wilkinson’s willingness to betray friends to get ahead, and his failures in military service paint a rather damning picture of a man ready to bend the rules to get the best for himself. Wilkinson’s name remains one of the most cursed of the post-Revolutionary era.

All photos: Wikimedia Commons