The Greatest Traitor in United States History

From a speech delivered to the Society of 1812 in Houston, Texas

Who was the greatest traitor in United States history? The first name that often comes to mind is Benedict Arnold. Benedict Arnold was an able military leader who switched sides during the War of Secession from Britain. The major turning point was after he managed obtaining command of West Point and then offered to surrender it to the British. His plan was found out when a courier was intercepted carrying a letter containing his plans. Once found out, he managed escaping capture by General George Washington and joined the British forces.

Even prior to the West Point episode there were allegations of corruption brought by his peers. Since he was an able military commander, these charges were dismissed or ignored. Although the term traitor has become synonymous with Benedict Arnold, there was another General whose conduct was even more treacherous.

General James Wilkinson served in the Continental army under Benedict Arnold. He also was ambitious and often self-serving. During the war, he developed enemies in political circles when he kept Congress waiting in the aftermath of the Continental victory at Saratoga. Wilkinson was smart enough to keep good relations with his peers. Although he irritated some Congressmen, he befriended many of the generals. He was one of the major conspirators in the Conway Cabal, which involved deposing of General George Washington and replacing him with General Horatio Gates. This plan amounted to a mutiny in the ranks of the Continental army. His involvement alienated him from Washington and brought him to court, where the case was dismissed. This was one of the first of his many victories in courts.

Wilkinson was very interested in Texas. After the war with Britain, he ventured into Spanish territory and began a series of dealings concerning land along the Mississippi. While in Spanish territory he swore allegiance to Spain in 1787. Wilkinson was given the designation of “Agent 13”. He kept his allegiance secret while at the same time maintaining cordial relations with American colonists in Kentucky. Part of his mission from Spain was to keep Kentucky out of American hands. He raised his own private army and built an outpost known as “Cantonment Wilkinson”. (This amounts to his own colonial version of Blackwater and setting up a large base of operations). This outpost was located in the present day state of Illinois.

After the Kentucky mission failed, he pressured the Spanish authorities to give him lands belonging to the Yazoo Indians in Mississippi. Wilkinson’s ambitions included advising the American adventurer Philip Nolan on what to do in the Texas territory. He sent Nolan into the territory, but also alerted Spanish authorities to the presence of an American intruder. Nolan was wise enough to stay in correspondence with Vice President Aaron Burr about Texas and his activities.

Vice-President Aaron Burr was working behind the scenes to organize an “unofficial” invasion of Texas. He wrote encoded messages to Wilkinson, who was then stationed in St. Louis, about the planned invasion. Somehow the Spanish discovered where Nolan was hiding out in Texas and ambushed him. Although some of his followers survived, Nolan was killed. Spain considered adventurers like Nolan “pirates”. Spanish authorities felt threatened by the misplaced ideas of liberties that the American States had.

As Wilkinson continued working on his Yazoo deal, his plans changed due to events in Europe and the Louisiana Purchase. In Europe, Napoleon invaded Spain and placed a relative on the throne of that nation, which distracted Spain from its colonial lands.

After securing the Louisiana Purchase, President Jefferson appointed James Wilkinson as Governor of the new territory. Jefferson also specified that Wilkinson must move his location to New Orleans. Although Wilkinson protested, which may have been for show, he moved to New Orleans. While serving as Governor, he gave secret orders to Zebulon Pike who was sent by the government to reconnoiter the new land acquired by the States. Wilkinson ordered Pike to veer off course into the Texas territory.

Pike and his party, which included a British spy, ventured off course and veered into the territory of Texas. His party was intercepted near the Rio Grande and brought to Santa Fe. Pike used the cover story that he was looking for the source of the Red River. While in jail, he discovered that many of the population wanted Mexico to be free from Spanish rule. He also heard news that an American officer (Walter Burling[1]) had been making trips to Mexico City. This was odd. It was unheard of that an American military officer was travelling that far in the interior of Mexico. Spain often considered such actions akin to spying and did not tolerate foreigners in their nation. Pike also gained some knowledge from the translator working with him. The man serving as translator for Pike was also a cartographer, which may have helped Pike gain knowledge of the area. Pike was released by Spanish authorities, and the incident was played off as an explorer getting lost in the wilderness.

[1] Prior to his service, Burling was a business man in Santo Domingo. He left that enterprise when the French Revolution and subsequent rebellions made the area unsafe. He manned the military installations in Haiti until the revolution subsided. Burling was later appointed to a justice position by Governor Claiborne of Louisiana.

By the time Thomas Jefferson finished his first term and Aaron Burr was elected Governor of New York, defeating Alexander Hamilton. Burr engaged in his episode with political rival Alexander Hamilton. Hamilton was an advocate of strong central government which Burr opposed. Hamilton accused Burr of planning the secession of New York from the Union, which Burr denied. Hamilton challenged Burr to a duel according to the traditional rules. Although dueling was illegal in New Jersey, since they were citizens of New York, they chose New Jersey as the location of the duel. After their duel, Burr returned to Washington to finish his term. He gave an emotional speech in the Senate prior to leaving. Burr departed with a collection of over 100 men on his journey to Texas. He had acquired leased land in Texas with the help of Baron de Bastrop and was going there with ‘armed farmers’ to take possession.

As Burr departed for his journey, Wilkinson met with the military Governor of Texas, supposedly to settle a boundary dispute. He hurriedly concluded the meeting and quickly traveled to New Orleans, leaving Captain Walter Burling. Burling travelled to San Antonio where he picked up a caravan of draft animals carrying some undisclosed items. Some historians claims it was payoff monies, yet Burling denied it being such, yet did not reveal what the contents were.

Burr was intercepted by Wilkinson, who made charges that Burr was guilty of treason for about to incite issues with the Spanish. The whole Hamilton duel episode was avoided. To support his claims, Wilkinson produced a handwritten copy of the coded letters, which he had altered to make them worse than what was originally there. Since he did not have the originals, the case was dismissed. Burr had also been in secret correspondence with ministers of Britain and Spain in Washington City. Burr was acquitted in the episode.

After collecting items in San Antonio, Walter Burling was later sent to Mexico City assuring Spain officials that Wilkinson just took steps to avert a conflict between Spain and the United States, and ask for a reward for those actions. He also smuggled out some cotton seeds from a strain that was particularly productive, taking them to his plantation in Natchez, Mississippi.

Wilkinson was also a key player in the Republic of West Florida episode. The British and American colonists used the manufactured crisis of Indian unrest to take over the territory from Spain. By stirring up the Indians, the colonists had reason to take arms and set up a government to protect them. After declaring independence, they were annexed by the United States in 90 days.

When the War of 1812 broke out Wilkinson was ordered to lead American troops in an assault on Canadian positions. His campaign failed. Wilkinson continued episodic involvements with Texas expeditions. He eventually died in Mexico in an opium den. He was known as the “General who never won a battle, but never lost a court case”.

Although Benedict Arnold is often seen as the greatest traitor, his second in command also switched sides, accepted monies from foreign governments to sabotage American policy, attempted a coup against General Washington, raised his own private army, and played the role of double agent. It also seems that he did not loose a public relations campaign either.