Jonathan Singleton Copley was the most prominent portrait painter of the American Revolution, even though he never truly took sides in the battle. Working between Boston and London for much of his life, he became one of America’s first internationally successful painters. He painted both American revolutionaries like Paul Revere and loyalist English subjects like George Watson, all while keeping his true political sympathies unknown. In this portrait of George Watson, a prominent colonial merchant and trader, Watson seems all business, but this portrait was likely a much more personal affair. Watson commissioned this portrait the year after his wife’s death, so he might hang it alongside the portrait Copley had painted of her the year before.