James Wilkinson: Image of Respectability

Wilkinson J 001James Wilkinson (1757-1825) is one of those characters in American history that one seldom hears about.  At the end of his life, he had achieved prominence as the senior officer of the U. S. Army, a politician, and one of the worst scoundrels in our entire history.

He was born just outside Benedict, Maryland on a farm adjacent to Hunting Creek.  His grandfather was a wealthy landowner who impressed upon his son and heirs that while the size of their property was comparatively small, they nevertheless belonged to a higher social class.  James was also taught that the image of respectability excused the reality of moral betrayal.  James’ father, Joseph Wilkinson, inherited the family property but had borrowed against it to such an extent that the family was actually debt-poor.  In 1764, the property (known as Stoakley Manor) was broken up and sold.  When Joseph died, his eldest son, also named Joseph, inherited what remained.  James was left with nothing beyond this one piece of fatherly advice: “… if you ever put up with an insult, I will disinherit you.” It may have been good fatherly advice, but it wasn’t anything that James could take to the bank.

James Wilkinson received his early education through a private tutor, funded by his grandmother.  He began his study in the field of medicine at the University of Pennsylvania, which was interrupted by the American Revolutionary War.  He married well, however, taking as his bride Ann Biddle who was the daughter of a prominent Philadelphia family.  Ann was a first cousin of Charles Biddle, an associate of Arron Burr [1].  It was this connection that helped propel Wilkinson into a career as a US Army officer and politician.  James and Ann produced four sons: John (1780-1796), James Biddle (1783-1813), Joseph Biddle (1789-1865), and Walter (b. 1791).  James and Walter also served as officers in the US Army.  After Ann’s death in 1803, James Wilkinson married Celestine Laveau Trudeau, the daughter of Chares Laveau Trudeau [2] in 1810.  With Celestine, he had three additional children: twin daughters and a son named Theodore, who was born in 1819.

Wilkinson’s military service began in 1775 when he joined Thompson’s Pennsylvania Rifles. He was commissioned a captain in September and served as an aide to Nathanael Greene during the siege of Boston. Wilkinson participated in the placement of field artillery on Dorchester Heights in 1776.  Following the British abandonment of Boston, James assumed command of an infantry company in New York.  In this capacity, he was sent to augment the forces besieging Quebec, then under the command of Benedict Arnold.  His arrival coincided with the arrival of British reinforcements under General Burgoyne.  The overwhelming British force caused the collapse of American efforts in Canada.  Wilkinson subsequently became a military aide to Arnold and departed Canada with Arnold on the last boat.  In August 1776, he was assigned to the staff of General Horatio Gates (known in history as Granny Gates), serving as an aide.

In 1777, Gates dispatched Wilkinson to carry messages to Congress reporting his victory at the Battle of Saratoga.  Wilkinson kept Congress waiting for this report while he attended to personal affairs. When he finally did show up, he concocted a story about how instrumental he was in Gates’ victory.  He was so good in his story-telling that Congress brevetted him a brigadier general.  He was twenty years old.

In this capacity, he was assigned as a member of the War Board.  His advancement to flag rank over colonels twenty or thirty years his senior caused an uproar of sorts.  Wilkinson was involved (to some extent) in the Conway Cabal [3], a secret conspiracy to replace George Washington with Horatio Gates in command of the Continental Army.  In any event, General Gates soon tired of Wilkinson and compelled his resignation in March 1778.  Afterward, sympathetic members of Congress managed to have Wilkinson appointed clothier-general of the Army, but he soon revealed a lack of aptitude for the position and ended up resigning from that position as well.

In 1783, Wilkinson accepted an appointment as a brigadier general of the Pennsylvania militia and became a member of the state assembly.  A year later, he relocated to Kentucky and began a clandestine effort to separate the territory of Kentucky away from Virginia [4].  His intrigues nearly caused a shooting war.  Then in 1787, Wilkinson managed to convince the Spanish governor of Louisiana, Esteban Rodriguez Miró [5] to grant Kentucky what amounted to a trade monopoly on the Mississippi River, which Spain then controlled.  Unbeknownst to almost everyone at the time, Wilkinson had applied for, was granted, and accepted Spanish citizenship.  He agreed to represent Spanish interests in the western territories and agreed to provide information to Spain about the inner workings of the Washington establishment, particularly relating to US plans for westward expansion.  Thus, while being paid for his services in Kentucky and Pennsylvania, he was also receiving a hefty stipend from Spain.

If anything, Wilkinson was a clever man —one capable of thinking outside the box.  In 1787, he signed an expatriation declaration and swore allegiance to the King of Spain to satisfy his own commercial needs.  When the scheme was finally revealed, it became known as the “Spanish Conspiracy.”  Wilkinson initiated the arrangement in a rather lengthy communiqué [6] to the Spanish governor concerning the political future of western settlers.  He intended to convince Spanish authorities to recognize Kentuckians as vassals of Spain. It should not surprise anyone, then, that upon his return to Kentucky in 1788, Wilkinson vigorously opposed the new Constitution of the United States.  Kentucky had almost achieved statehood under the Articles of Confederation and there was considerable disappointment within Kentucky when statehood was delayed because of the enactment of the new Constitution.

In the period leading up to Kentucky’s seventh convention regarding its separation from Virginia, Wilkinson campaigned for Kentucky’s union with Spain.  He was a charming man; his charisma got him elected as a committee chairman at the convention.  He first argued for Kentucky to seek independence from Virginia, and then for the union of states.  At the time, many Kentuckians believed that joining the United States must be predicated on the US’ ability to arrange a treaty with Spain governing free navigation of the Mississippi River.

When Wilkinson was unable to gather sufficient support for his position, he approached Miró with a proposal—one favoring Wilkinson above all others.  In exchange for his efforts on behalf of Spain, he asked for a grant of 60,000 acres of land at the junction of the Yazoo River and the Mississippi (near present-day Vicksburg).  The acreage would suit him as a refuge should his supporters be forced to flee from persecution in the United States.  He also asked Miró for a pension of $7,000.00 (roughly $190,000 today) at the same time he requested money from prominent Kentuckians.  By 1788, however, Wilkinson had lost the confidence of Spanish authorities and Governor Miró was officially forbidden from giving any money to support a revolution in Kentucky.  Secretly, however, Wilkinson remained on the Spanish payroll for many years.

In 1791, Wilkinson led a force of Kentucky volunteers against native Americans.  In October of that year, he was commissioned a lieutenant colonel and appointed to command the 2ndU. S. Infantry.  In the next year, President George Washington was faced with reorganizing the Continental Army as the Legion of the United States [7].  Washington also had to decide who would lead it.

Washington’s two major candidates for leading the Legion were James Wilkinson and Anthony Wayne [8].  Wayne was chosen to serve as the Senior Officer of the U. S. Army over Wilkinson, primarily due to Wilkinson’s (then) suspected involvement with the Spanish government.  Washington, being aware of Wilkinson’s fragile sense of self, promoted him to brigadier general.  Nevertheless, Wilkinson was intensely jealous of Wayne and contemptuous, and Wayne reciprocated in kind.

Wilkinson’s pettiness led him to openly criticize Wayne’s leadership.  It was too much for Wayne, who opened an investigation into Wilkinson’s involvement with the government of Spain.  Throughout this period, Wilkinson had renewed his secret Spanish alliance and, on several occasions, notified Governor Francisco Luis Héctor de Carondeletto the intentions of both the US and France relating to western movement and occupation.  When Spanish couriers were intercepted carrying cash payments to Wilkinson, Wayne, with suspicions confirmed, attempted to court-martial Wilkinson for his treachery.  Wayne died before a judicial proceeding could be convened.

Despite Wilkinson’s treachery, he began his first tenure as Senior Officer of the Army, which lasted for about 18 months.  In 1798, the cabinet transferred Wilkinson to the southern frontier and placed him third in ranking in the Army, behind George Washington (who died in 1799) and Alexander Hamilton.  It was Hamilton who tasked Wilkinson with creating a reserve force for US Army in the lower Ohio River Valley.  The purpose of this reserve was a contingency plan to seize the lower Mississippi River and New Orleans from France [9] and its Spanish ally.  The crisis with France ended in 1800, Hamilton left the Army, and Wilkinson continued to plan for this war through 1802.

Wilkinson once more became the Senior Officer of Army in the summer of 1800, serving under President Thomas Jefferson.  At the time of the Louisiana Purchase, Wilkinson and Governor William Claiborne officiated at the transfer of the territory in 1803 —at a time when Wilkinson continued to receive a pension from Spain in exchange for information about the US intentions toward territorial expansion.  It was Wilkinson who informed the Spanish about the Lewis and Clark expedition.

In 1804, Wilkinson met with Vice President Aaron Burr and entered into a conspiracy with him.  The original idea was General Wilkinson’s but Burr, whatever his faults, was a man of action.  Making what he thought was a secret arrangement with Wilkinson, the plan called for Wilkinson to resign as Senior Officer of the Army and assist Burr detaching Texas, New Mexico, and perhaps even Mexico itself from New Spain.

In 1805, Burr made a westward trip to gain support, recruit men, and acquiring arms and shipping to carry them down the Mississippi.  By this time, he was no longer serving as Vice President.  Wilkinson, however, had overplayed his hand and began having difficulty keeping the US and Spanish officials from discovering what he was up to.  Should Spain ever reveal his secret dealings, especially the fact that Wilkinson was a citizen of Spain, the result could be a firing squad. Wilkinson realized that he was nearly at the end of his rope.  What he did next was near-brilliance, even if immoral.  He wrote a letter to President Jefferson informing him that he was on the trail of a grand conspiracy.  Jefferson was immediately interested, so Wilkinson next identified the name of the traitor: Aaron Burr.  In the minds of President Jefferson and a large part of the political elite, there could not have been a better candidate for such a charge.  Aaron Burr was already unpopular; making him into an traitorous ogre was relatively easy.

Wilkinson reported to Jefferson that in order to confirm the extent of this traitorous behavior, he would need a large sum of money. Jefferson authorized it without much deliberation.  Cunningly, Wilkinson never accused Burr of conspiring against Texas or New Spain. Filibustering was not treasonous.  He instead charged Burr with conspiring to separate Kentucky and the Louisiana territory from the United States. It was Wilkinson who ordered Burr’s arrest.

General Wilkinson was the sole source of allegations against Burr, and the government’s principal witness.  Whatever else this did —Burr was acquitted on a technicality— it effectively silenced Burr from revealing what Wilkinson was up to.  So, in addition to his dishonesty, Wilkinson was also a clever gambler.  Some historians now claim that all Wilkinson’s plots and counterplots were hatched for only one reason: to alarm Spain.  A worried Spanish government was more likely to pay Wilkinson money for information.

The so-called Burr conspiracy shook the US government. Imagine —a Vice President of the United States who conspired against his own country [10].  Best of all, no one was looking in Wilkinson’s direction.  It was a perfectly executed deception.

General Wilkinson sent edited parts of this story to Madrid, for which the Spanish paid handsomely.  Wilkinson then arranged a meeting with Simón de Herrera, Commandant of the Louisiana frontier.  Herrera had been ordered to patrol the area between the Sabine River and the Arroyo Hondo (a small tributary of the Red River) to protect New Spain’s northern frontier from American encroachment.  Wilkinson proposed that the border situation could be amicably settled.  Herrera agreed to accept a buffer zone between the Sabine River and Arroyo Hondo, which tapered the official US border by seven miles.  Since the arrangement was favorable to Spain, Herrera was happy to accept the so-called Neutral Ground Agreement.  Wilkinson might have been in serious trouble for giving United States territory away, but the clever Wilkinson had read Jefferson correctly: the last thing he wanted was a war with Spain.

General Wilkinson testified at Burr’s trial, but it was essentially Wilkinson’s own doctored evidence against Burr that saved him from being convicted of treason.  Moreover, Wilkinson’s testimony was largely regarded as self-serving —the effect of which made Burr seem to be an inept victim of an overzealous government.  He nearly indicted himself  for misprision of treason [11].  In any case, a much-worried Wilkinson imposed martial law on the city of New Orleans and had several individuals (and their lawyers) arrested and detained until after Burr’s trial.  Detention guaranteed that none of these persons could link Wilkinson to Burr.  One clear-eyed court official opined that he may have never seen a greater villain than General Wilkinson.

It wasn’t long after the end of Burr’s trial that the public became aware of Wilkinson’s likely involvement.  There were two Congressional inquiries into his private affairs.  President James Madison, succeeding Jefferson in 1809, ordered a military court of inquiry in 1811.  Wilkinson was court-martialed but exonerated.  He continued to serve as Senior Officer of the Army until 1812 when Henry Dearborn [12] was promoted to Major General over Wilkinson.

After the outbreak of the War of 1812, Wilkinson was elevated to the post of major general and led the forces that occupied Mobile, in Spanish West Florida.  The operation brought the city of Mobile into the Mississippi Territory.  After Dearborn stepped down from his post as Senior Officer in 1815, Wilkinson was assigned to the St. Lawrence River area of military operations where he led two failed campaigns.  Wilkinson was relieved of his command and appeared before a military inquiry who determined that he was not guilty of malfeasance.  Nevertheless, Wilkinson was discharged from the US Army on 15 June 1815.

iwilkio001p1Wilkinson’s military career was finished, but he was a long way from giving up his sleazy behavior.  While serving as US Envoy to Mexico in 1821, Wilkinson requested a grant of land in the province of Tejas.  He was waiting for a formal reply from the government of Mexico when he passed away, aged 68-years.  Wilkinson was buried in Mexico City —which was entirely fitting.

The full story of Wilkinson’s shenanigans was never revealed until 1854 when Charles Gavarré published Wilkinson’s correspondence with Esteban Miró.  Beyond this, Wilkinson’s activities have confounded historians ever since.  In 1865, then Governor of New York Theodore Roosevelt (himself a historian) pronounced Wilkinson a villain.  Military historian Robert Leckie [13] said of Wilkinson, “…he was a general who never won a war or lost a court-martial.”


  1. Jacobs, J. R.  Tarnished Warrior: Major-General James Wilkinson (New York: MacMillan), 1938.
  2. Weems, J. E.  Men Without Countries (Boston: Houghton Mifflin, 1969)


[1] Aaron Burr (1756-1836) was a prominent attorney, politician, and third Vice President of the United States.  He served during the administration of Thomas Jefferson’s first term of office.

[2] Charles Trudeau (also known as Don Carolos Trudeau) was acting mayor of New Orleans and the Surveyor-General of Spanish Louisiana (1780s-1805).

[3] The British Army captured Philadelphia in the Fall of 1777.  At that time, Philadelphia was the seat of the Second Continental Congress, which in light of the British advance, was forced to relocate to backwater Pennsylvania.  Many senior officers and members of Congress began to question Washington’s leadership and his management of the war effort.  Gates, on the other hand, was seen as a general who could get things done. Disaffected officers, headed by Brigadier General Thomas Conway, began a series of letters that criticized Washington behind his back.  When the matter was made public, Conway resigned, and Gates issued Washington a public apology.

[4] Kentucky County (also spelled Kentucke) was formed by the Commonwealth of Virginia from the western portions (beyond the Cumberland Mountains) of Fincastle County in 1776. The county was abolished in 1780 when it was divided into Fayette, Jefferson, and Lincoln counties.  These were collectively known as the Kentucky District of Virginia.  Kentucky was finally admitted to the Union in 1792, it’s fifteenth state.

[5] Spanish military officer and governor of Spanish-American provinces of Louisiana and Florida.  In 1779 during the American Revolution and the Anglo-Spanish War, Miró was a part of the forces commanded by Bernardo de Gálvez in campaigns against the British in West Florida.  Gálvez appointed Miró as acting Governor of Louisiana, which was part of New Spain, in 1782.  He became a proprietary governor in late 1785.  Spain had taken over this territory from France after the latter’s defeat in 1763 by Great Britain in the Seven Years’ War.

[6] Encoded with a myriad of symbols, numbers, and letters that were decoded by a reasonably complex English-Spanish cipher code-named “Number 13”.  This was the basis for Wilkinson’s pseudonym, “Agent 13.”

[7] Reorganization of the Continental Army also required an expansion, replacing state militias with professionally trained officers and enlisted men.  Between 1792-1796, the LUS was composed of four sub-legions, each with its own infantry, cavalry, and artillery.  The catalyst for this reorganization/expansion was the defeat of General Arthur St. Clair’s defeat on the Ohio frontier in1791 and the need to assert US sovereignty over the Miami Indian territory in northern Ohio and Indiana.

[8] Wayne (1741-1796) was known for his fiery personality and fearless conduct in battle, which earned him the sobriquet “Mad Anthony.”  He was born in Pennsylvania and was eventually buried there but also served the State of Georgia as a member of the US House of Representatives.

[9] The Quasi-War was an undeclared war fought almost entirely at sea between the USA and France from 1798 to 1800 during the presidency of John Adams.  After the French Monarchy was abolished in September 1792 the United States refused to continue repaying its large debt to France, incurred during the American Revolution.  The US made the argument that its debt was owed to the King of France, not the French Republic that replaced the monarchy. France was understandably outraged but added to this the Jay Treaty between the US and Great Britain.  France authorized privateers to conduct attacks on American shipping, seizing numerous merchant ships, and ultimately leading the U.S. to retaliate.

[10] Burr was not the last high-ranking politician to conspire against his country for personal gain.

[11] A finding of guilty would be imposed upon someone who has knowledge that treason is being committed but does nothing to stop it.

[12] Colonel Dearborn was advanced to Major General and assigned to serve as Senior Officer of the U. S. Army in 1812.  By this time, he had already had a distinguished career as a warfighter, member of congress, US Minister to Portugal, and Secretary of War.

[13] Leckie (1920-2001) was a historian and author who served during World War II with the 1stMarine Division in the Pacific.

About Mustang

Retired Marine, historian, writer.
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6 Responses to James Wilkinson: Image of Respectability

  1. Andy says:

    We tend to think of the men of this era as larger-than-life stalwarts who built this country by their heroic deeds. This guy was an ass. He was interesting, but as ass, nonetheless.

    Liked by 1 person

    • Mustang says:

      One of the lessons we should all have learned from history is that land speculation was the entire purpose of the British (and other European country’s) colonies from the very beginning. It was true in the early colonial period, true in the founding era of the United States, true in the westward migration of early Americans, true in Mexican Tejas, true in the aftermath of the Mexican-American War, and it is true today. People will do almost anything to acquire wealth, and an expedient way to accomplish it is through land acquisition and land sales. So, I think you are right to say that many of these “founding” stalwarts were “in it for themselves,” but that in and of itself isn’t necessarily a bad thing. What is bad, in many cases, is how far they were willing to go in order to achieve it. Wilkinson did have the appearance of respectability, but you’re right … he was a real ass —and, got away with it. I think Leckie nailed it pretty well.

      Thanks for weighing in, Andy …

      Semper Fi


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