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==Kentucky ventures==
After his resignation from the Continental Army, Wilkinson reluctantly became a [[brigadier general]] in the [[Pennsylvania militia]] in 1782 and also a state assemblyman in 1783, due to the wishes of George Washington.<ref name="Linklater"/>{{rp|62}} He moved to [[Kentucky]] (at that time, just three counties still belonging to Virginia) in 1784, and he was active there in efforts to achieve independence from [[Virginia]]. In Kentucky, Wilkinson in 1788 vigorously opposed the new [[U.S. Constitution]]. Kentucky had very nearly achieved statehood under the old [[Articles of Confederation]], and there was widespread disappointment when this was delayed because of the new constitution.
In April 1787, Wilkinson made a highly controversial trip to [[New Orleans]], which was the capital of [[Louisiana (New Spain)|Spanish colonial Louisiana]].<ref name="Linklater" />{{rp|80}} At that time, Americans were allowed to trade on the [[Mississippi River]], but they had to pay a hefty [[tariff]].<ref>{{cite book|last=Slaughter|first=Thomas|title=The Whiskey Rebellion|year=1986|publisher=Oxford University Press|location=Oxford|pages=55}}</ref> Wilkinson met with Spanish Governor [[Esteban Rodríguez Miró]] and managed to convince him to allow Kentucky to have a trading monopoly on the River; in return he promised to promote Spanish interests in the west.<ref>Buescher, John. "[http://teachinghistory.org/history-content/ask-a-historian/24290 Trailing Lewis and Clark]". [http://www.teachinghistory.org Teachinghistory.org]. Accessed 12 July 2011.</ref> On August 22, 1787, Wilkinson signed an expatriation declaration and swore allegiance to the King of Spain to satisfy his own commercial needs.<ref name="Linklater"/>{{rp|86}} The "Spanish Conspiracy", as it is known, was initiated by Wilkinson's "First Memorial", a 7,500-word report written before he left New Orleans for [[Charleston, South Carolina|Charleston]], to the Spanish concerning the "political future of western settlers" and to convince Spain to "admit us [Kentuckians] under protection as vassals".<ref name="Linklater"/>{{rp|85}} This was encoded with myriad symbols, numbers, and letters that was decoded via a complex English-Spanish cipher code-named "Number 13", which became the basis for his pseudonym, "Agent 13".<ref name="Linklater"/>{{rp|88}}▼
Leading up to Kentucky's seventh convention regarding separation from Virginia in November 1788, Wilkinson attempted to gauge the support for Kentucky to seek union with Spain. Wilkinson's ability to win people over with his charm and seeming sincerity got him elected committee chairman at the convention. He advocated for Kentucky to seek independence from Virginia first, and then to consider joining the [[United States|Union of states]] as a second step. For many, joining the Union was conditional upon the Union negotiating with Spain to arrange free navigation on the Mississippi River, a contentious point which many doubted the eastern states would act upon.
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General Wilkinson may not have been a competent commander in conventional operations in the [[Battle of Crysler's Farm]] and the [[Battle of Lacolle Mills (1814)|Battle of Lacolle Mills]], but he excelled at guerrilla warfare tactics. Before the [[Battle of Bladensburg]], General Wilkinson helped conceive a strategy of using the militia dominated forces as guerrilla fighters against the incoming British attack on the Capitol. Wilkinson and other American commanders tried to convince the American government to use all the militia in hit-and-run tactics, ambushes, and harassment against the British forces by the flanks and rear. But President James Madison and James Monroe disapproved of the plan. Madison and Monroe wanted to fight a set piece battle by placing the militia in linear defensive formations to fight the British head on. This led to ultimate disaster and defeat as the British easily routed the militia and burned the Capitol.<ref>"Neither Victor nor Vanquished: America in the War of 1812" by William Weber Page.136.</ref>
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▲In April 1787, Wilkinson made a highly controversial trip to [[New Orleans]], which was the capital of [[Louisiana (New Spain)|Spanish colonial Louisiana]].<ref name="Linklater" />{{rp|80}} At that time, Americans were allowed to trade on the [[Mississippi River]], but they had to pay a hefty [[tariff]].<ref>{{cite book|last=Slaughter|first=Thomas|title=The Whiskey Rebellion|year=1986|publisher=Oxford University Press|location=Oxford|pages=55}}</ref> Wilkinson met with Spanish Governor [[Esteban Rodríguez Miró]] and managed to convince him to allow Kentucky to have a trading monopoly on the River; in return he promised to promote Spanish interests in the west.<ref>Buescher, John. "[http://teachinghistory.org/history-content/ask-a-historian/24290 Trailing Lewis and Clark]". [http://www.teachinghistory.org Teachinghistory.org]. Accessed 12 July 2011.</ref> On August 22, 1787, Wilkinson signed an expatriation declaration and swore allegiance to the King of Spain to satisfy his own commercial needs.<ref name="Linklater"/>{{rp|86}} The "Spanish Conspiracy", as it is known, was initiated by Wilkinson's "First Memorial", a 7,500-word report written before he left New Orleans for [[Charleston, South Carolina|Charleston]], to the Spanish concerning the "political future of western settlers" and to convince Spain to "admit us [Kentuckians] under protection as vassals".<ref name="Linklater"/>{{rp|85}} This was encoded with myriad symbols, numbers, and letters that was decoded via a complex English-Spanish cipher code-named "Number 13", which became the basis for his pseudonym, "Agent 13".<ref name="Linklater"/>{{rp|88}}
This was during the period of the [[Mexican War of Independence]] against Spain, which was won in 1821. In that year, Wilkinson requested a [[Mexican Texas|Texas]] land grant. While awaiting the Mexican government's approval of his land scheme, Wilkinson died in [[Mexico City]] on December 28, 1825, at the age of 68. He was buried in Mexico City.<ref name="Joseph2007" />▼
Wilkinson's involvement with the Spanish (as Agent 13) was widely suspected in his own day, and it was proved in 1854, with Louisiana historian [[Charles Gayarré]]'s publication of the American general's correspondence with [[Esteban Rodríguez Miró]], [[Louisiana (New Spain)|Louisiana]]'s colonial governor between 1785 and 1791.<ref name=":0" />
==Last years==
▲After the end of his military career, Wilkinson unsuccessfully sought to be appointed as [[U.S. Ambassador to Mexico|U.S. Envoy to Mexico]]. This was during the period of the [[Mexican War of Independence]] against Spain, which was won in 1821. In that year, Wilkinson requested a [[Mexican Texas|Texas]] land grant. While awaiting the Mexican government's approval of his land scheme, Wilkinson died in [[Mexico City]] on December 28, 1825, at the age of 68. He was buried in Mexico City.<ref name="Joseph2007" />
==Later view==
Some 65 years after the general's misdeeds, then-Governor of [[New York (state)|New York]], [[Theodore Roosevelt]], condemned him in print: "In all our history, there is no more despicable character."<ref name="Stewart"/> Historian [[Robert Leckie (author)|Robert Leckie]] characterized him as "a general who never won a battle or lost a [[court-martial]]", while [[Frederick Jackson Turner]] called Wilkinson "the most consummate artist in treason that the nation ever possessed". [[George Rogers Clark]] biographer Temple Bodley said of Wilkinson, "He had considerable military talent, but used it only for his own gain."<ref name=":0">{{Cite book |last=Broadwater |first=Robert P. |url=https://books.google.com/books?id=TPBZDgAAQBAJ&pg=PA158 |title=American Generals of the Revolutionary War: A Biographical Dictionary |date=2012-02-23 |publisher=McFarland |isbn=978-0-7864-6905-5 |pages=158}}</ref> It has been speculated but never proven that Wilkinson had Anthony Wayne assassinated by poison. Wilkinson is documented secretly undermining him throughout his later career, benefited from his death, and would replace him as commander after his death.<ref>{{Cite web|url=https://allthingsliberty.com/2013/08/was-general-anthony-wayne-murdered/|title=Was General Anthony Wayne Murdered?|first=Hugh T.|last=Harrington|date=August 20, 2013|website=Journal of the American Revolution}}</ref><ref>{{Cite web|url=https://historynewsnetwork.org/article/159602|title=Why I Believe Meriwether Lewis Was Assassinated | History News Network|website=historynewsnetwork.org}}</ref>
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