James Wilkinson

Although largely forgotten now, Major General James Wilkinson committed more acts of treason than his former mentor, Benedict Arnold, ever did. Wilkinson shrewdly endeared himself to those in power, despite being considered an "unprincipled imbecile" by his contemporaries. Every president from Washington to Madison trusted him, and he was put in charge of the entire army. Unbeknownst to them, Wilkinson was a valued spy for the Spanish government. Wilkinson is also believed to have conspired with former vice president Aaron Burr in a plot to separate the western territories from the rest of the United States to create their own kingdom. When Burr was arrested, Wilkinson turned on his co-conspirator to save himself. Although Wilkinson was court-martialed, he was acquitted. In the end, charm could not save him from two failed invasions of Canada, and his military career ended in disgrace. Only after his death did his treason become known.