John was born in 1737. He is the son of John Bolling and Elizabeth Blair. He married Mary Jefferson, the sister of the future President, and they were the parents of Archibald Bolling, John Bolling, Martha Bolling , Edward Bolling, Mary (Polly) Bolling, Robert Bolling, Thomas Bolling, Ann Bolling, Jane Bolling and an unnamed son that died as an infant.
John and Mary were ancestors of the controversial First Lady, Edith Bolling Wilson.
John's brother Robert wrote of him in 1764: 
John Bolling possessed some of his father's dispositions: was like him, very large, and was six feet high. He delighted for the chase, and cared very little for the ladies, until he saw his lady. His character then as suddenly changed as that of Silvio in the Pastor Fido. After many sighs &c., he married Miss Jefferson, daughter of that Jefferson who, with Mr. Fry, made a map of Virginia.
The state of things at Chesnut Grove is truly distressing. Mr B.'s habitual intoxication will destroy himself, his fortune & family. Of all calamities this is the greatest. I wish my sister could bear his misconduct with more patience. It might lessen his attachment to the bottle, & at any rate would make her own time more tolerable.
Will of John Bolling. Chesterfield Co., VA, WB 5, pp. 291-293, w. 7 Feb 1800, no notation of when the will was proved. Digital image at Ancestry.com
my wife (unnamed) - all my land in Chesterfield Co.
son Edwd Bolling - land in Goochland county
son John Bolling - land in Goochland county
son Robert Bolling - land in Albemarle county
son Archibald Bolling - land in Campbell county, land in Chesterfield county
grandson Jefferson Archer
Exrs: sons Edwd Bolling, Robt Bolling, Archd Bolling
Wit: Thos (Lasen ?), Henry Walthall, _?_ Fuqua
Bolling, John, son of Col. John Bolling, of "Cobbs", lived first in Gloucester County from which he was a delegate in the House of Burgesses in 1766-1769. Afterwards, in 1778, he was a member of the House of Delegates from Chesterfield County. He married Mary, sister of Thomas Jefferson. He was born June 24, 1737, and died in 179-."
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