John Baylor, c. 1722
Grandson of a planter who traded profitably in several Tidewater counties, and son of a planter and burgess from Gloucester and then King and Queen counties, John Baylor III (1705–1772) was third-generation Virginia aristocracy. As heir to a dynasty, he was sent to England for early education at Putney Grammar School, followed by study at Cambridge. There, presumably at about age seventeen, he commissioned this portrait, an example of provincial English art. It is thinly painted, without a great deal of virtuosity, as distinct from the lavish London portrait of Robert Carter III—which is of the same type—as are contemporary portraits produced in Virginia. Nonetheless, the painting served quite well its purpose of documenting the sitter's successful passage through English society.
Most striking about this image is the young sitter's confident, even haughty attitude, which is conveyed by his assertive deportment and costume. Still but a boy, Baylor wears an adult wig and carries a sword. To judge from this image, he had been well instructed in England to take his privileged place in society. In Virginia in 1726 he patented a large tract of land in Caroline County and built a one-and-a-half-story, wooden H-plan house, now lost, a structure relatively large for its time and place. There this portrait hung. Baylor named his estate Newmarket after the famous racecourse near Cambridge in England, where he had learned about horse breeding and racing. He devoted his adult life in Virginia to the former, with more financial success than most who invested in horses.