US Hall of Shame: General James Wilkinson, the Donald Trump of the US Military

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James Wilkinson Key Life Events

• Infantry officer and then military aide for Benedict Arnold during the invasion of Canada.
• Ordered to deliver news of the victory at the Battle of Saratoga to Congress, but purposely delayed reporting the news and went home instead. When he finally delivered the news, he boasted and embellished his own role so much that he was promoted to general and to the Board of War despite being only 20 years old.  
• As an aide to General Horatio Gates, takes part in the Conway Cabal aimed at replacing George Washington with Horatio Gates as Commander-in-Chief. Wilkinson writes a drunken letter that gives away details of the scheme, ushering in its failure. In retaliation, Gates compels Wilkinson to resign. 

• In 1787, Wilkinson traveled to Spanish-controlled New Orleans to open trade for his personal business. American trade was restricted, so he swore allegiance to the King of Spain so he could make more money.
• In 1788, strongly opposed the US Constitution, probably because a weaker government would allow him to get away with more shenanigans. 
• Chairman of the committee to separate Kentucky from Virginia. He disagreed that a new state automatically joined the US and was hoping to side Kentucky with Spain. When it seemed like KY would be forced to join the US, he attempted to get money and land in the Yazoo from Spain for pro-Spanish Americans to flee to. 
• In 1791, Wilkinson led a controversial raid that unites the tribes during the Northwest Indian War, giving them the centralization to defeat the US Army under Gen. St. Clair soon after. During Wilkinson's raid peace initiatives were planned and he ruined these. 
• Pres. Washington makes Mad Anthony Wayne the Senior General of the US Army. Wilkinson was considered the alternative for this spot, but Washington knew of rumors that Wilkinson could be in Spanish pay. Wilkinson continuously spread negative info about Wayne in newspapers (anonymously) and in letters to politicians as he was passed over for the top spot. Wayne learns that a Spanish courier is caught with payments meant for Wilkinson and is on the verge of court-martialing him before his sudden death. Wilkinson becomes the Senior General on Wayne's death.
• Wilkinson is replaced as Senior General when John Adams makes former Pres. George Washington the senior general and, at Washington's urging, Alexander Hamilton as 2nd in command. Wilkinson falls to 3rd in line. 
• Wilkinson became Senior General again following Washington's death and Hamilton's resignation in 1800. Wilkinson would serve the top spot from 1800 to 1812. Wilkinson maintained his connection to Spain to receive payment and would clue the Spanish in on events, such as the Lewis & Clark expedition. 
• In 1804 and 1805, Aaron Burr and Wilkinson engaged in what became the Burr Conspiracy. Wilkinson was a perfect participant as he was both the Senior General and the Gov of Louisiana territory. Wilkinson is all in on the plan until late 1806 when it seemed likely that the plot would be exposed or that Wilkinson's own Spanish-connections would be exposed. He writes Pres. Jefferson and alerts him of Burr's conspiracy, while projecting his own innocence. At the Burr trial, Wilkinson's obvious self-serving behavior and tampered evidence sees him nearly given a treason trial of his own. To prevent evidence against him, he places New Orleans under martial law and arrests people who may have known of his connection to Burr. Wilkinson is not court martialed for his Burr Conspiracy activities but he is removed as Gov of Louisiana Territory. 
• In 1811, several officers called for Wilkinson's removal as encamped troops were reporting heavy casualties due to endemic diseases. Wilkinson refuses to relocate the troops or improve their camp equipment while making sure he is personally away from the diseased areas. This is sometimes called the Wilkinson Affair by some historians. Pres. Madison considers court martialing and removing Wilkinson, but he's convinced not to do so as Wilkinson is popular in Pennsylvania. 
• Madison finally removed Wilkinson as Senior General in 1812 after Wilkinson led two failed campaigns during the War of 1812. He was discharged from the military in 1815. 
• Following his military service, he was made Envoy to Mexico. He died in 1825 in Mexico City while attempting to get a land grant in Texas for himself. His Spanish connections were strongly rumored throughout his life, but the US Gov consistently gave him the benefit of the doubt. It wasn't until several decades after his death that they were proven. Here's some interesting quotes about Wilkinson from Wikipedia:
  • Theodore Roosevelt, condemned him in print: "In all our history, there is no more despicable character."^[5] Historian 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."^[45]