The son of Henry Middleton of Middleton Place and younger brother of Arthur Middleton, signer of the Declaration of Independence, Thomas inherited The Oaks plantation in Berkeley County, South Carolina. Like many other young Charlestonians of his social standing, Thomas was sent to England to continue his education, but returned at the approach of British hostilities in January 1774. This portrait is one of several of Middleton family members West painted between 1770 and 1772. Besides a few patrons from Philadelphia, the Middletons were the only other Americans West painted after he moved to England. Stylistically, Thomas Middleton's portrait is among those works by West that demonstrate the influence of Anton Raphael Mengs, whom the artist met and copied during his travels to Rome.