James Wilkinson was born to an upper-class family on March 24, 1757, in Maryland. He entered Pennsylvania State University to study medicine; however, his education was interrupted due to the American Revolutionary War. Throughout the war, he served in the Pennsylvania Rifle Battalion as captain and eventually was promoted to 5th and 8th Commanding General of the United States Army. He became the first Governor of Louisiana Territory in 1805 and served in this position for two years; he was later removed after accusations of abuse and court-martialed by President Madison but was found innocent. In the War of 1812, Wilkinson was promoted to Major General. After two failed campaigns in the war, he was removed from service but subsequent investigation cleared him of wrongdoing. Wilkinson published an autobiography in hopes of clearing his name. Wilkinson died on December 28, 1825.

Winthrop Sargent was born on May 1, 1753, in Gloucester, Massachusetts. After graduating from Harvard University in 1771, Sargent served on his family’s merchant ship. During the American Revolutionary War, he served with the Gridley Massachusetts Regiment and was promoted to captain lieutenant in Knox's regiment. After the war, he served in the Northwest Territory. In June 1786, Sargent was appointed as a surveyor to lay out the new territory's townships. He was appointed by Congress as secretary of the Northwest Ordinance of 1787. President John Adams appointed Sargent as the first Governor of the Mississippi Territory in 1798 and served as governor until 1801. He died on June 3, 1820 in New Orleans, Louisiana.