Isham Randolph, c. 1724
As a young man, Isham Randolph (1685–1742), third son of dynasty founder William Randolph I, rejected Virginia plantation life for what neighbor William Byrd II called Randolph's "own element, the Sea." Byrd was instrumental in 1710 in winning for him command of the Henrietta, a merchant ship with a ten-man crew and four guns. In the same year Randolph sold his Virginia land and took a house in London. For the next decade he worked the tobacco trade on the James River that he had sailed as a child. In 1717 he married Londoner Jane Rogers. By 1720 he quit the sea and was listed as a London merchant. Around 1725, he resettled in Virginia his growing family of three, soon to be nine, children. Before leaving England, Randolph apparently sat for this portrait. Though its surface is now abraded, the painting displays a quality of conception and execution that suggests the hand of a London-trained artist of talent.
The impression generated by this image is a sense of the sitter's sophistication, proper rearing, and confidence. This portrait and Randolph's biography give credence to the statements of 1724 by historian Hugh Jones that at least some prominent Virginians by then had markedly "improved in wealth and polite living" and "live[d] in the same neat manner, dress[ed] after the same modes, and behave[d] themselves as the gentry in London."
Randolph's daughter Jane would marry Peter Jefferson; Thomas Jefferson was their son.