Individual Details

James is most often seen as married to Elizabeth Gentry because of the following record:

Nicholas Gentry wrote his will 20 Apr 1777 before leaving Louisa Co; it was received for probate in Albemarle Apr 1779. He left his wife Jane in possession of his real & personal estate during her life. Gifts to sons Martin & Nathan, grandson Bartlett & granddaughter Patty, children of Martin. Sons Moses, David, & Nicholas & daughter Mary only 20 sh [Moses & David had previously rec'd land, Nicholas had land rec'd from his father-in-law, doubtless Mary had also rec'd her share], One equal share of remaining estate to Robert, Benajah, Nathan & Martin and dau Elizabeth Haggard. One-half share to granddaughters Jane Timberlake & Ann Jenkins. Executors: wife Jane, sons David & Martin. Wit: Bezaleel & Benajah Brown.
Some have interpreted this will to be that of the first Nicholas Gentry - the immigrant - but it is not - it is the will of his son Nicholas II. His daughter Elizabeth was a generation younger, born 1731, and married to James' son Nathaniel.
I have also seen a "Mabel" Gentry as married to Nathaniel Haggard. In the Gentry research, James and Nathaniel are said to have been sons of Anthony Gentry but this is also questionable - the elder James did perhaps have sons named both James & Nathaniel but he had no brother that has been proved..


Here is another explanation of the confusion regarding which James Haggard married an Elizabeth Gentry:
Journal of Gentry Genealogy, Vol 1, Issue 9, Sept 2001
http://www.gentryjournal.org/archives/jgg0109.htm
A Digression Concerning the Haggards
There are frequent references in genealogical listings of the presumed founder of the Haggard family of Virginia, as a James Haggard who landed in Norfolk County, Virginia shortly after 1700. There is an interesting story about James being hired as an indentured school teacher. James and a young lady connected with the school were said to have been attracted to each other and ran away to North Carolina in 1706 because as an indentured servant James supposedly could not marry in Virginia. James and his wife then returned to Virginia at a later time. The original source of this story, a book "The History of the Haggard Family in England and America, 1433 - 1899", published by David Dawson Haggard in 1899, quotes this story and other colorful information about James but does not name his schoolgirl wife. Since the publishing of that book, some members of the Haggard family have provided the name of Elizabeth Gentry, oldest daughter of Nicholas-I, as this wife, while others have claimed the youngest daughter of Nicholas, Mabel Gentry was the wife. Still others have reported that first Elizabeth and then Mabel were wives of James.
The story of James and his proposed marriage with Elizabeth Gentry may have some elements of truth, such as James being a schoolteacher, but most of the story is undoubtedly false considering the following facts:
The only town in Virginia in 1706 was Jamestown, so any school in which James may have taught must have been operated informally, probably by the parish, either in a local church building or in a private home on one of the plantations. At that time only boys would have received education and no girls would have been among James' students, certainly none sent from a distant location.
It is very difficult to imagine how a seventeen-year-old daughter of a small tobacco plantation owner on the western fringes of Virginia settlement, would have travelled to the coast and met James in Norfolk County.
The story of fleeing to North Carolina is particularly questionable, that state not being divided from South Carolina until 1712. The first town in North Carolina was not settled until 1705 when the Bath was founded in Pamlico Sound. The closest church where a marriage could have been performed was undoubtedly Charleston, now South Carolina. Unlike present conditions where it is just a short distance from Norfolk across the state boundary to North Carolina, in 1706 it would obviously have been impossible to travel there by land, and equally impossible by sea given the lack of coastal shipping.
Since the proposed relationship did not originate with the Haggard family book but was added afterwards, it appears to me that some Haggard/Gentry genealogist in filling out a pedigree chart, skipped a couple generations by mistake, and confused the original James Haggard with the James Haggard who was a son of Elizabeth and Nathaniel, who did indeed marry an Elizabeth Gentry.

FamilySearch tree has a very different set of children and I believe belongs to a very different James Haggard - the children are Nathaniel, Edmund and Gray (Granville) - and Zachariah.

Birth	Abt 1680	Overwharton Parish, Stafford County, Virginia
Marriage	1705	Overwharton Parish, Stafford County, Virginia -
Death	Abt 1770	Louisa County, Virginia

Child	James Haggard (1709 - )
Child	Richard Haggard (1711 - )
Child	William Haggard (1712 - )
Child	John Haggard (1717 - 1748)
Child	Mary Haggard ( - )
Child	Frank Haggard (1721 - )
Child	Nathaniel Haggard (1723 - 1806)
Child	Edmund Haggard (1725 - 1811)
Child	Gray Grandville Haggard (1728 - )
Child	Zachariah Haggard (1730 - 1760)