General Matthew Clarkson was born in New York in 1758. After the beginning of the American Revolutionary War in 1775, he joined the New York Fusiliers as a gentleman-private, fighting with the regiment in the Long Island campaigns. He was assigned to the Northern Army in 1777 and went on to serve in numerous important engagements throughout the war. Clarkson was a founding member of the Society of the Cincinnati, a hereditary-patriotic society which sought to preserve the ideals and loyalties of the officers of the Continental Army. This portrait shows Clarkson proudly wearing the Society’s eagle on his lapel. Clarkson served as a member of the New York State Assembly between 1789 and 1790, where he introduced a bill for the gradual abolition of slavery in the state, though slavery was not abolished in New York until 1827. As a Regent of the University of the State of New York, he was presented at the court of French King Louis XVI, and later served as State Senator between 1794 and 1795. Clarkson owned considerable amounts of land in New York and, in 1819, the town of Clarkson, in the north west of the state, was established in his name.

James Frothingham trained in the Boston studio of Gilbert Stuart, one of America’s foremost painters of the late-18th Century. Stuart is reported to have said that ‘no man in Boston but myself can paint so good a head’ as his pupil (see W. Dunlap, History of the Rise and Progress of the Arts of Design in the United States, II, New York, 1834, p. 216). Frothingham had a prosperous career and went on to become an important painter in his own right. In 1831, he was elected an Academician at the National Academy of Design in New York. The present painting is a copy after Stuart's portrait dating to circa 1974, now in the Metropolitan Museum of Art, New York (inv. no. 38.61). The present portrait was commissioned from Frothingham in the mid-19th Century by the sitter’s grandson, Dr. John Clarkson Jay, a New York physician and noted conchologist, remaining in the family until 2013.