Henry Middleton remained an unmarried widower for four years after his 2nd wife Maria Henrietta’s death, but in January 1776, he became the fourth husband of Lady Mary Mackenzie Clarke Drayton Ainslie. Lady Mary was born in Scotland, the daughter of George Mackenzie, third Earl of Cromartie. She came to Charleston in 1757 as the second wife of Thomas Drayton of Magnolia plantation. Drayton soon died and she married John Ainslie, another wealthy Low Country planter, who died in 1774. Harriott Pinckney Horry, Lady Mary’s goddaughter, described her as “not handsome but elegant, very clever and shrewd, a staunch friend and a capital woman of business.” Her marriage to Henry Middleton spanned the turbulent years of the American Revolution and the death of his daughter Sarah Pinckney. Lady Mary again found herself a widow when Henry Middleton died on June 13, 1784. Two years later she journeyed to Scotland to secure her portion of her late father’s estate. She died at sea on the return voyage to Charleston in 1788.