The Gordon portraits depict the family of an Ulster merchant and planter of Scottish origin who emigrated to Lancaster County in 1738. Through trade with merchants in the British Isles and the West Indies, voracious land purchasing, and active public service, James Gordon quickly rose to prominence, which he celebrated in 1751 by commissioning a sizeable group of large, expensive portraits of himself, his successive wives, his three children, and his brother who had emigrated with him. Posed in contemporary clothing before grandiose, artificial settings of an outdated seventeenth-century portrait tradition, the sitters seem provincial.
The commission for the Gordon portraits seems to have resulted simply from the sudden availability in Virginia in 1751 and 1752 of artist John Hesselius or Robert Feke. Both appeared in the colony at this time; Hesselius emulated the style of the much more accomplished Feke. Four additional Gordon children who lived to maturity, born between 1752 and 1765, were apparently never painted.