Following info is extracted from General Winfield Scott's autobiography. Maybe it will shed some light on his family history and give some clues to research. It reads: "According to the family Bible, I was born June 13, 1786, on the farm which I inherited, some fourteen miles from Petersburg, Virginia. My parents, William Scott and Ann Mason, both natives of the same neighborhood, intermarried in 1780. William's father, a Scotchman, of the clan Buccleuch, was the younger son of a small landed proprietor, and taking part with the Pretender, escaped from the field of Culloden (1746) to Bristol, wence, by the aid of a merchant and kinsman, he was smuggled on board of a ship bound to Virginia, and buried himself in that colony before 1747, the date of the general amnesty."
It further reads: "In my sixth year, I lost my father -- a gallant lieutenant and captain in the Revolutionary army, and a successful farmer. Happily, my dear mother was spared to me eleven years longer. And if in my now protracted career, I have achieved anything worthy of being written; anything that my countrymen are likely to honor in the next century -- it is from the lessons of that admirable parent that I dirived the inspiration. Perhaps filial piety may be excused for adding a few sentences more on the parents and collateral kindred of this lady -- the daughter of Daniel Mason and Elizabeth his wife, the only child of John Winfield, probably the wealthiest man in the colony. The latter survived his daughter, and dying intestate, about 1774, Winfield Mason, the brother of Mrs. Ann Scott, took, by descent, as the law then stood in favor of the eldest mail heir, the whole of the landed estate of the grandfather -- besides sharing equally in the personal property with his two sisters. I, his namesake, stood nearly from my birth, the principal devisee, in an uncancelled will that I read after my uncle's death, of nearly the whole of that large estate; but marriage and the birth of a child, very properly, abrogate a testament of a prior date..."
With the above said, based on family history and various newspaper obits, my GG grandparents were supposed to be somehow distantly connected to General Winfield Scott through the Winfield family line. If anyone has any further information on the Winfield connection (Brothers and or parents of John Winfield) I'd sure like to see it.