In 1749 the Nottoway Indians returned to the court house. Isle of Wight County had been divided and the court was now in Southampton County, Virginia. Some of the names of the Chief Men are the same as appeared on the 1735 deeds. Among the new names are George Skipper and Watt Bailey. In 1723 a George Skipper was sued in Chowan County by George Allen for absconding with his indentured servant, Mary Bailey. The court record says he ran away with Mary Bailey on December 17, 1719, and harbored and entertained her until August 30, 1722. The trial began in July, 1723. George was in jail when the trial began, but we don't know if he had been since August of 1722. Allen sued for four hundred and ninety-three pounds and won, but only got ten pounds. George got ten days, five pounds fine, and court costs. Curiously, Mary sued George for her travel expenses and was awarded sixteen shillings, eight pence. Named in the suit as justices of the peace directed to take depositions are two of the Indian trustees, Thomas Cock and John Simmons.
This is much discussed on message boards, and some assumptions are made about Mary Bailey but again without sources. It is said that she was Watt Bailey's daughter and George Skipper's wife eventually. This might be true, but which George Skipper? In 1728 George Skipper and wife, Mary sold land in Bertie County, North Carolina, and it seems logical that if he was sufficiently enamored of Mary Bailey to "entertain" her illegally for three years, that he would likely marry her when she was free of indenture. Let's not forget, though, that she also sued him. Maybe it was just a spat. It is also perfectly feasible that she was the daughter or sister of Watt Bailey. The problem is we don't know when George Skipper, the son of 1668 George Skipper was born. Typically one expects the first son to be born while the father is in his twenties. If we assume that 1668 George was in his twenties when he patented the land at Potacassi Swamp and had son George, who I'll call Senior, shortly thereafter, then George, Sr. would be near fifty in 1719 and would seem a little old to be gallivanting with a servant girl, but again, they were Skippers. Still this seems to identify the culprit as George, Jr. who might be coming of age around 1719. The fact that no George Skipper was present at the signing of the 1735 deeds causes some confusion however. We might expect that he appeared as a Chief Man fourteen years later when he had come of age, but if that were the case he would have been too young in 1719 to be "harboring and entertaining" Allen's servant girl. The earliest reference I have found to George Skipper, Jr. is an abstract of a 1724 court case when he was again sued by a Bailey, although which Bailey is not recorded. His absence in 1735 may have been due to other reasons, or he may not have ascended to the rank of Chief Man.
There are twelve 1749 deeds. The Chief Men who signed each of them are Frank, Sam, Watt Bailey, John Turner, George Skipper, and John Will. They are called bluntly Indians. It does not say some Indians and the white man with the big nose. The list of the Chief Mens' names is simply followed by the appositive, Indians. Assuming 1668 George was an English immigrant, George, Jr. must be only one quarter white. Ten of the deeds are dated January 1, 1749, the fifth in sequence is dated January 2, 1749, but the sixth through the eleventh are again dated January 1. The last is dated in its text ________ September, 1749, but the memorandum at the end of the deed is dated January 1, 1749. The deeds do not appear on consecutive pages of the deed book, and unrelated deeds in between have wide date spreads. Parcels in both the Circular and Square reservations were sold. A transcript of the first deed in the sequence follows. Images of the sale of a parcel from the Circular and Square Reservations are attached.