The name Fortune is not used by the Gilliam family until after Capt. Hinchea Gilliam married a Fortune. (It has been said that this Fortune is the daughter of a Walter Flood; however, the Will of Walter Flood dated 1722 refers to his granddaughter, Fortune, as Fortune Flood, not Fortune Gilliam. By 1722 Hinchea Gilliam and Fortune would have been married for several decades, so there is some debate as to whether she was a Flood or not.)
Hinchea Gilliam and Fortune have one granddaughter named Fortune, the daughter of Charles Gilliam and Mary Jones, his wife. It has been erroneously stated that Mary Jones, wife of Charles Gilliam was Mary Clanton:
“Charles and Mary (CLANTON) GILLIAM are listed in the "Albemarle Parish Register" as being the parents of five children: Fortune (b. 1742), Lydia (b. 1744), Phoebe and John, twins, (b. 1751) and Jordan (b. 1757)." [James L. McLemore, III, pp. 69, 70].
That is not the case. Mary Clanton, daughter of John Clanton, mentioned in the Will of John Clanton dated 1781, married John Gilliam son of Hinchea Gilliam and Mary Johnson, his wife, not Charles Gilliam.
Charles Gilliam, the father of Fortune Gilliam born 1742, married Mary Jones, not Mary Clanton:
Surry County VA Court Records, 1712-1718, Book VII
The last will and testament of Arthur Jones Deced was presented in Court by Prudence Jones his Execrx. who made oath thereto and being proved by the oaths of William Briges and Wm Beech, Witnesses thereto is admitted to record and on the mocon [sic] of these said Prudence Jones and her performing what is usual in such cases certificate is granted her for obtaining a probate thereof in due form.
Surry County Deeds, Wills, etc., 1715-1730
18 Mar 1723
Charles Gillum and wife, Mary Gillum, of Isle of Wight county to John Doby of Surry County for 20 pounds current money. . . 90 acres on south side of Nottoway River in Southwarke Parish (being part of 400 acres granted to Henry Jones and lately in the tenure of Robert Webb in right of his wife Prudence Webb, now deceased, who was the mother of said Mary Gillum. Mary Gillum's father was Arthur Jones, decd., whose will was dated 22 Jan 1715).
Charles (X) Gillum
Mary (X) Gillum
Rec: 18 Mar 1723
It also should be noted that it has been said that James McLemore Jr., son of James and Fortain, married a Jones, a Nancy Jones.
Now, back to our topic, if John and Margary had a daughter Fortune born between 1665-1771, and knowing naming patterns, and the Gilliam’s preference for using given names over and over again; it is quite surprising that there are no Fortune Gilliams until 1742 (seventy years later).
Given the above, the lack of primary sources, and the fact that a Fortune is not represented in the settled of the estate of Margary Gilliam Briggs in 1688, leads me to believe that it is very unlikely that there was a Fortune Gilliam, daughter of John and Margary.
It appears, rather, that James Macklemore’s wife Fortain was a member of one of the families in Virginia at the time that was using the name Fortune such the Jordans—Charles Gilliam and Mary Jones, even name a child Jordan Gilliam.