When Charles Willson Peale painted this portrait in January 1819, Andrew Jackson was in Washington to answer congressional questions about his military conduct in Florida. The Monroe administration had sent him to deal with the Seminole Indians, who were raiding Alabama and Georgia from Florida. Believing he had permission to pursue the Seminoles into Florida and seize the territory from Spain, he invaded and executed two British subjects he thought were instigating the Indians. Many in Congress believed that Jackson had exceeded his authority.

Peale, then seventy-six, had heard rumors that Jackson might challenge his critics to a duel. The artist “felt disposed” to give him advice, “fearful that he might as a military man, seek that abominable & too prevalent custom of settling injuries by duels.” Jackson, his notoriously bad temper notwithstanding, was gentle with those he liked. He explained to Peale that duels of honor could not be avoided, and patiently sat for his portrait.