My guess is that the invidual you have listed as Lucy Olive Drake (who married Samuel Shepard Ligon) is very likely a daughter of the individual I have as Ann Southall (who married ?James? William Drake),
Amelia County, Virginia Will Book 6, Pages 220-221. Transcribed 25 August 1988, Susan Shields Sasek:
[Page 220] . . .
"Item I lend unto my daughter Ann Drake twenty five acres of Land which land I purchased of Archer Perkinson in Amelia during her life & at her death to be"
"be equally divided among all of her children. Item my will and desire is that after the above mentioned legacies are [rais]ed that a division take place equally among my children & that part of my Estate that shall fall to my daughter Ann Drake to be deposited in the hands of my Exors that shall be hereafter named to be given to her as they shall [can't read] [can't read] stand u[can't read] and if their [sic] should be any of her part remaining at her death my desire is that it be equally divided among her children."
This will was signed on 15 Aug 1801 & recorded 2 Nov 1801. (I have my transcription & a copy of the will online: http://freepages.genealogy.rootsweb.com/~sassytazzy/southall/death/wills/willjamessouthall1801.html
I've never been able to find a marriage record for this Ann Southall and until recently didn't know anything else about her other than what her father stated in his will.
A fellow Southall researcher recently sent me a copy of a 1906 letter from Hon. Herman H. Southall to a "cousin" in Petersburg, VA (probably Martha Southall Butterworth, but she is not named in the letter). On the first page of this letter, he states that "Ann Southall married James Drake" and then lists a few of her children: Rebecca (md "Walls of NC"), Elizabeth (md "Bowery of Charles City Co." VA), Lucy (md "Liggon of NC"), Mary (md "Parker") and according to the transcription "Deedra? and Theoderick Drake".
According to the book "Marriages of Amelia County, Virginia 1735-1815", compiled by Kathleen Booth Williams, published by the Genealogical Publishing Co., Inc., Baltimore, 1979 (first published in 1961). According to Ms. Williams, she copied "the Register, Index to Marriage Bonds" at the "Clerk's Office at Amelia; then, as many original bonds, consents and Ministers' Returns as one may consult were checked."
In the next paragraph, she states that 2 drawers of old records are closed to the public by Court order as they are too fragile, and that the "bonds in these drawers were copied by the Clerk, each on a separate sheet of paper and each is signed by him." Ms. Booth states that the first part of the Register was compiled by Mr. Stephen L. Farrar, Sr., "who was Judge of Amelia County from 1898 to 1907," he was then appointed "County Clerk and Clerk of the Circuit Court of Amelia. It was during the following years he compiled the Register." According to Ms. Booth, the first part of the Register is in Mr. Farrar Sr.'s handwriting and his son ("Mr. Farrar, Jr.") completed where Mr. Farrar, Sr. stopped, taking the Register through marriages of 1950.
On page 69 of this book is the entry:
"11 November 1809. LIGON, Samuel and Lucy H. Drake, dau. of William Drake. Sur. John Southall. p. L-1"
"28 January 1808. BOWRY, William and Elizabeth B. Drake, dau. of William Drake, who consents. Wit. to consent, Thos. Worsham, A. Coleman and Jesse Southall. Sur. Thomas Worsham. p. B-5" (note that the 1906 letter from Hon. Herman H. Southall stated that Ann Southall married James Drake & that among her children, Lucy Drake married a Liggon of NC and Elizabeth married Bowery of Charles City Co. VA.
Henry H. Southall (my ancestor) was one of the executors of James Southall's will (the other, Daniel, was living in NC, Henry was still in Amelia Co., VA). In the general index (of grantors) to Amelia Co., VA deeds, I found the following entry: Grantor: Henry H Southall (Exr), James Southall (by Exr); Grantee: James W. Drake; Deed Book: 23 Page: 555 Year: 1813.
Henry H. Southall and Daniel Southall (executors of James Southall's 1801 will) were brothers of Ann Southall Drake, and of Jesse Southall (all of these children are mentioned in the will, among others). I do not believe that all of James Southall's children are listed in his will by name and it is possible that another of his sons is named John Southall (note John Southall was security for marriage Lucy Drake and Samuel Ligon).
Information from another Southall researcher is that Ann Southall married James W. Drake -- I don't have anything to prove that though. I also have not seen the name "Olive" given to any of the Southalls.
Since I've only recently received this information, I haven't done any of my own research along these lines; however, I thought I'd post the information I have for your records -- hopefully it will help you.
I have a Southall web site online -- if you'd like to see any of the records there, here is the url:
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