James Wilkinson is the most fascinating American historical figure you likely know nothing about. Americans nearly deify their heroes from the founding period (Washington, Jefferson, Hamilton), and even emphasize the infamy of their villains as larger than life (Benedict Arnold, Aaron Burr). But Wilkinson was a strange amalgamation of both these things. For that, as well as other issues, he has been largely forgotten despite the outsized role he played in the early history of America.
Wilkinson made his first marks on history during the Revolution. An aide to Nathanael Greene during the Siege of Boston, later personal aide to Benedict Arnold during the failed Canadian campaign, and finally personal aide to General Horatio Gates, Wilkinson was involved with some of the most significant men and events of the Revolution. After the Battle of Saratoga, Gates sent Wilkinson to officially inform the Continental Congress of the victory, and he used that opportunity to creatively embellish his own role in that victory, and was breveted a Brigadier General at the tender age of twenty. But through casual bragging at a dinner party he managed to entangle himself in the infamous Conway Cabal, which eventually resulted in his fighting a duel with General Gates and resigning from the army. By the age of twenty he had already established both his reputation for military competence and as a man of suspect character.
But it was Wilkinson’s career after the Revolution that is most fascinating. He moved to Kentucky, where he both failed as a businessman, and became a secret agent in the pay of the Spanish government. As part of what became known as the Spanish Conspiracy, Wilkinson attempted to influence Kentuckians to separate from the United States and join the Spanish Empire. Yet, despite being widely suspected of being an agent of Spain, he was once again made a brigadier general and made second in command to General Mad Anthony Wayne when Washington reorganized the army to fight the Northwest Indian War.
After the army’s victory at the Battle of Fallen Timbers which brought that war to an end, Wilkinson feuded with his commander, filing formal complaint against him with President Washington. Wayne, in turn, opened an investigation into the allegations that Wilkinson was an agent of Spain, and prepared to launch a court martial against him, but Wayne died suddenly, and instead of court martial, Wilkinson became the senior officer of America’s army. America’s top general was also the top secret agent for a competing foreign power.
But it was the Burr Conspiracy that brought Wilkinson to the apex of both glory and infamy. Originally collaborating with Burr, planning to use command of the army to help the conspiracy succeed, Wilkinson had a change of heart. Perhaps fearing that Burr could fail and that he himself would then be ruined, Wilkinson turned against him and informed President Jefferson of the conspiracy. After double crossing Burr (and thus saving his country) Wilkinson became entangled in the ugly and high profile trails of the former Vice President, and his act of subverting the conspiracy tarnished his reputation more than any of his actual intrigues with the Spanish power ever did.
In addition to these accomplishments, intrigues, double crosses and treasons, Wilkinson served as the first governor of the Louisiana Territory (during which time he tipped off the Spanish about the Lewis and Clark Expedition), was a United States Indian agent who negotiated several treaties with the Chickasaw and Choctaw, and was promoted to Major General during the War of 1812, where he gained control of the Mobile District of West Florida (the only territorial gains of the war), but his campaigns in Canada ended disastrously.
Wilkinson is, without a doubt, one of the most interesting figures in American history. His long career of service and treasons to his country, his uncanny ability to avoid being found guilty of his intrigues despite being widely suspected, the fact that the three first presidents all found it expedient to make use of his talents despite being aware of his reputation — all of this adds up to a fascinating story. It’s almost a crime that he is as forgotten as he is, but this excellent biography goes a long way toward amending that oversight. Highly recommended.