James Wilkinson: America's Greatest Scoundrel

By Thomas Jewett This moniker belongs to James Wilkinson; a man who lied and cheated throughout his entire life. He was a traitor who sold his citizenship to a foreign country. He was a spy and a fomenter of rebellion. And, he was also the ranking general in the army of the United States while he committed these deeds. James Wilkinson, America's Greatest ScoundrelJames Wilkinson was born in Benedict, Maryland, in 1757. He began his career in the army in 1775 when he enlisted under Benedict Arnold’s command. It was rather apropos that Arnold was Wilkinson’s mentor. He was given the rank of captain because of his education. He was with Arnold in the unsuccessful attempt to take Montreal. Wilkinson obtained the rank of Major in 1776 and was transferred to Horatio Gates’ staff. With Gates, who thought he was an outstanding officer, he was promoted to a Colonelcy, and appointed Adjutant-General. During this time, Wilkinson would first show his true colors as a scoundrel. During the battle of Bemis’s Heights in 1777, a Colonel John Hardin, under very dangerous circumstances, had penetrated enemy lines to spy on British positions. On returning to the American lines Hardin reported his findings to Wilkinson. Wilkinson went right to Gates with the information, but made himself out to be the hero of the daring adventure. This information led to Burgoyne’s surrender, and Wilkinson was rewarded by being allowed to bear the victory’s tidings to the Continental Congress. Gates in his message to Congress also recommended that Wilkinson be promoted to Brigadier-General. For some reason, Wilkinson was rather tardy in carrying the dispatch and Congress censured him for the delay. Later, Wilkinson would be brevetted to Brigadier and made Secretary of the Board of War. This Board of War, of which Gates was a member, was a hotbed of conspiracy to have Washington removed as Commander in Chief of the Continental Army. This plot has become known as the Conway Cabal, named for General Thomas Conway who wrote a letter to Gates severely criticizing Washington. Wilkinson, supposedly in his cups, repeated a phrase purportedly from this letter to William Alexander. (It has been conjectured that Wilkinson purposively leaked this information so he could gain some advantage for himself.) Alexander repeated it to Washington, who then sent the quotation back to Gates. Gates would ultimately apologize, but those officers tarnished in the affair lost influence and position. Wilkinson resigned his brevet commission and the only job he could find was as Clothier-General of the Army. He was forced from this position when charged with irregularities in his accounts. It is reported that he attempted to instigate a duel between Cabal and Alexander in the aftermath of the affair. Duly unemployed, Wilkinson tried his hand at farming in Pennsylvania. Past history aside, he was also given the rank of Brigadier General of the Pennsylvania Militia. It can be assumed that he was not very successful in either venture since he moved to the Kentucky Territory in 1784, hoping to improve his financial situation. His status as a veteran and general put him in the forefront of frontier Kentucky society. By 1785 Wilkinson was deeply involved in the politics of Kentucky and its efforts to achieve separation from Virginia. He was in the forefront of fomenting dissatisfaction in joining the Union. New Orleans, under Spanish control, had closed the port to American commerce and many Kentuckians could see little value in an alliance with the United States. Hoping to make his fortune in the Mississippi River trade Wilkinson obtained a commercial concession with Spain and an annual pension of $2,000.00 from the Spanish government. For this, all he had to do was sell out his country. As part of the bargain Wilkinson campaigned for Kentucky to become an independent country allied to Spain. He so pleased his Spanish masters that his stipend was increased to $4000.00 in 1787 when he swore allegiance to Spain and became Spanish Secret Agent #13. It is during this time that Wilkinson destroyed the reputation of one of the giants of the American Revolution, George Rogers Clark. Clark was seen as a threat by the Spanish. They believed that General Clark was a possible western strongman capable of invading Spanish territory. Wilkinson convinced the Spanish Governor that he alone could thwart Clark. Wilkinson also coveted two important posts held by Clark: General of the Militia and Indian Commissioner. Wilkinson spread rumors that Clark was a “sot” and drunkard and could not be trusted to Virginian officials. He was so effective that Clark lost his positions, fortune, and reputation. Wilkinson was named Indian Commissioner. Foreign bribes and trading concessions did not seem to help Wilkinson’s financial affairs. He applied, in 1791, for reinstatement in the army and was appointed a Lieutenant Colonel under the command of Anthony Wayne. He would lead a force of Kentucky Volunteers on a successful campaign against Ohio Valley tribes and because of this would be promoted once again to General. Wilkinson would spend his four years under Wayne, publicly quarreling with his superior and privately questioning his sanity and intelligence. He was so effective in his smear campaign that Wayne became known as “Mad” Anthony Wayne. Wilkinson was with Wayne at the Battle of Fallen Timbers and it was reported that he intentionally delayed sending a supply train to his commanding general in an attempt to undermine Wayne. This duplicity was ignored and he was given command of Detroit in 1796. When Wayne died, Wilkinson became the Commander in Chief of the U.S. Army because of his time in grade. A Commander who was still in the pay of Spain and who was characterized by General Knox as an individual with “conduct tarnishing the military reputation of our country.” In 1798, the citizens of Detroit protested his greed so much that Wilkinson was transferred and named Commander of the Army’s Southern Department. After arriving in the South, Wilkinson wheeled and dealed in land speculation and Army contracts. During this time he was put under surveillance by the government, which was later withdrawn by Jefferson. In fact, Jefferson so fully trusted Wilkinson that in December of 1803, the President commissioned him to take possession of the Louisiana Purchase on behalf of the United States with William Claiborne. While in New Orleans Wilkinson would reestablish his contacts with the Spanish and was reported to have received a $12,000 bribe. With this money he purchased a boatload of sugar and took it to New York to sell. While in New York he would meet with Aaron Burr, Jefferson’s vice-president. Wilkinson and Burr were old acquaintances, both having been on Arnold’s staff during the Revolutionary war. The two, aware that war between the United States and Spain over boundary disputes was a possibility, made plans to invade and colonize Spanish territory in the West. They also schemed to establish and independent “Empire of the West” on a Napoleonic model with New Orleans as capital. Wilkinson was now plotting against his paymasters. The plot may have been more Wilkinson’s than Burr’s. Burr was quoted as describing Wilkinson as “the projector” of the conspiracy and as having said that he “would never have thought of such designs but for the importunities of Wilkinson.” While in the East, Wilkinson would contact the Spanish ambassador and inform him of the Lewis and Clark Expedition. He inferred to the Spanish envoy that the American force would be infringing in Spanish territory and that troops should be immediately sent to capture them. Several hundred Spanish horsemen would scour the plains that summer, acting on this intelligence, to no avail. Burr was dropped by Jefferson from the presidential ticket but not before he convinced the President to appoint Wilkinson as governor of Northern Louisiana. This position would allow Wilkinson to move freely about the West without suspicion. The conspirators could now begin to put their plan into effect. In August 1804 Vice President Burr contacted Anthony Merry, Britain’s Minister to the United States. Burr informed Merry that Louisiana was ready to break with the U.S. and once it did all the western country would follow suit. All he needed was a half a million-dollar loan and a British naval squadron at the mouth of the Mississippi River. The British might have entertained the requests but Prime Minister Pitt died and in the new English leader was adverse to the plan. Having failed to secure British aid, Burr journeyed West to gain support for the enterprise. While in the West he would meet Wilkinson at Fort Massac in the Illinois country to finalize plans. Burr continued to New Orleans and in 1806 was welcomed by many like-minded individuals. By this time rumors about Burr’s activities had filtered to the East and had even been published in newspapers. Meanwhile, the border conflict with Spain had intensified. Jefferson ordered Wilkinson, to the Sabine River on the Spanish border. Jefferson wanted the Spanish pushed back across the river, which would mean invading Spanish territory. This did not fit into the conspirator’s plans. Their ploy was for Burr and Wilkinson to attack Spanish territory together in the name of the United States and then declare themselves rulers of the conquered lands. Burr, at the time, was nowhere near the Sabine. Wilkinson vacillated and against direct orders negotiated a neutral zone between the opposing forces. This was easy for him to accomplish since he was in the pay of the army he was to attack. For this service he demands 150,000 pesos from the Spanish government for refusing to fight, which was never paid. Burr sent a coded letter (to become known as the infamous “Cipher Letter” at Burr’s trial) to Wilkinson, which stated he was ready to initiate their plan. He then set out in August 1806 to collect supporters for his army. This caused the trickle of rumors to become a torrent. Wilkinson became fearful and as usual opted to save his own hide. On October 9, 1806 Wilkinson sent a letter to Jefferson outlining Burr’s actions but painted himself as being innocent. Jefferson ordered Burr’s arrest. The former Vice President was apprehended near Nachez, Mississippi while trying to escape to Spanish territory. In May 1807 Burr was tried for treason. Chief Justice John Marshall, a Jefferson foe, found the defendant not guilty. Wilkerson avoided indictment because he had Jefferson’s protection. Jefferson, though, could not ignore Wilkinson’s ineptitude in his role as Governor of Louisiana. The populace of the area became so angry at his administration that troops had to be deployed to restore order. Meriwether Lewis replaced him. Jefferson’s successor, Madison, was not so disposed toward Wilkinson. He had Wilkinson court martialed in 1811 for mismanagement, complicity with Burr, and with being in the pay of Spain. Wilkinson was barely acquitted for lack of evidence, which would later become accessible after he was out of the army. During the War of 1812 Wilkinson was transferred to the Northern Department. He was given command of an army of more than 7,000 men and was to take Montreal. On November 11, 1813 he was stopped in his advance by a force of just 800 British soldiers at the Battle of Chrysler’s Farm. Incredibly, the following March, this time at the head of 4,000 men he was repulsed by 180 of the enemy. He would face a court of inquiry and unbelievably was exonerated for his ineptitude. But, this was the last straw; Wilkinson was discharged from the service at the end of the war. He was not through with Spain though. Using the guise as an agent of the American Bible Society, he traveled to Mexico City and bilked the government out of a Texan land grant. He lived in Mexican Territory the rest of his life, dying in 1825, reportedly from the effects of smoking opium. How could such a man rise to a position of power and maintain it in view of a continuous record of avarice and deception? Wilkinson was a consummate flatterer who ingratiated himself with the powerful and a master at denigrating those who stood in his way. Jefferson was, perhaps, most at fault in keeping this traitor in positions of authority. Wilkinson was “a good Democratic Republican” and that was all Jefferson wanted to know. Whatever the reasons, James Wilkinson stands as one of America’s greatest scoundrels.
Tom Jewett is presently an Assistant Professor at McKendree College. He retired from Southern Illinois University-Edwardsville three years ago and holds the title of Professor Emeritus from that institution.