Colonel Robert Bolling (December 26, 1646July 17, 1709), sometimes called Robert Bolling, Sr., after he gave a son his own name, was a wealthy early American settler planter and merchant. Ancestry and early life Robert Bolling was the son of John Bolling (b. 1615) and Mary Carie (née Clarke) Bolling. He was named after his grandfather Robert Bolling; his grandmother was Anne Clarke. He was born at Tower Street, All Hallows, Barking Parish, in London on December 26, 1646. His father John, was one of the Bollings of Bolling Hall, near Bradford, England. Robert's ancestry could be traced to Robert Bolling, Esquire, who died in 1485 and was buried in the family vault in the church of Bradford. On October 2, 1660, at the age of fourteen, Bolling arrived in the colony of Virginia. In 1674, he married Jane Rolfe, daughter of Thomas Rolfe, the son of Pocahontas. They had one son, John Bolling (January 26, 1676 – April 20, 1729). Jane Rolfe Bolling is believed to have died shortly after their sons birth. John Bolling married Mary Kennon, daughter of Richard Kennon and Elizabeth Worsham, and they had seven children. Second marriage In 1681, after his first wife died, Col. Bolling married his second wife Anne Stith, daughter of John Drury and Jane (Gregory) Stith. They had the following children together: Robert Bolling Jr. (1682–1749), married Anne Mary Cocke. Robert was the grandfather of Beverley Randolph, the eighth Governor of Virginia. Robert and Anne were also the great-grandparents of Anne Custis – wife of Robert Edward Lee. Stith Bolling (1686–1727), married Elizabeth Hartwell. Captain Edward Bolling (1687–1710), married Ms. Slaughter died of smallpox at sea. Anne Bolling (1690–1750), married Robert Wynne. Drury Bolling (1695–1726), married Elizabeth Meriwether. (Elizabeth's brother Nicholas Meriwether was a great-great-grandfather of Captain Meriwether Lewis the explorer.) Thomas Bolling (1697–1734). Agnes Bolling (1700–1762), married Richard Kennon. The descendants of Robert Bolling's first marriage are sometimes referred to in family history forums as "Red Bollings" due to the Native American lineage of Jane Rolfe's grandmother Pocahontas. These "Red Bollings" include prominent descendants such as Edith Bolling Wilson, wife of U.S. President Woodrow Wilson. Bolling's great-grandson, Robert Bolling, was one of the most prolific poets in colonial Virginia. The descendants of his second marriage are referred to as "White Bollings". Career and death As a successful merchant and planter, Bolling acquired a large estate, Kippax Plantation. He was