Virginia Winns Part 6: Competing Theories About the Hanover Winns

There is a lot of speculation about the Winn family of Hanover County, Virginia on the web. You can find it on trees posted at, at the Winn DNA Project website, and Winn message boards. I get a perverse kick out of this, because there is very little that the few extant Hanover records (and records from counties between Hanover and the coast) actually prove about the Hanover Winn family in the first half of the 18th century.

In fact, a mere three deeds contain a good bit of what we can actually prove about the early Hanover Winns. Here they are:

  1. 3 January 1733, John Winn of St. Paul’s Parish, Hanover Co., carpenter, to Benjamin Hawkins, same, for 2,000 lbs. tobacco and £15 current money, 140 acres grantor purchased from Richard Leak of Hanover. Witnesses were Richard Winn, Phebe Winn, and John Winn.[1]
  2. 19-20 January 1733, deeds of lease and release from Richard Winn and his wife Phebe of St. Paul’s Parish, Hanover, to John Winn of the same, £82 for 517 acres with plantation on Chickahominy Swamp in Hanover purchased by said Phebe in her widowhood by name of Phebe Pledger from John Hogg of New Kent. Witnesses were John Winn, Ann Wheeler, and Mary Pledger.[2]
  3. 31 Jan – 1 Feb 1733, deeds of lease and release from John Winn of St. Paul’s Parish, Hanover, to Richard Winn of the same, £100 for 517-acre plantation on Chickahominy Swamp in Hanover purchased by Phebe Pledger from John Hogg of New Kent. Richard and Phebe Winn sold to John Winn 19-20 Jan. last. Elizabeth Winn, wife of John, relinquished dower. Witnesses were John Winn, Ann Wheeler and Mary Pledger.[3]

OK, what do these three deeds tell us?

  • the three Winn men (Richard, John, and John Winn) who appeared in these deeds were undoubtedly family.
  • all three men were of legal age by 1733, so they were all born by 1712.
  • the first John Winn, grantor in deed #1, may have been unmarried in 1733 because relinquishment of dower wasn’t mentioned.
  • the second John Winn, grantor in deed #3, had a wife named Elizabeth.
  • Richard Winn’s wife was Phoebe, and she was previously married to a Mr. Pledger.
  • the witness to two of the deeds, Mary Pledger, was surely related to Phoebe in some fashion.

We can consider these matters proved by these deeds, except perhaps for the question whether John Winn, the grantor in deed #1, was married.

With this information in our arsenal, let’s get down to brass tacks: where did these Hanover Winns live before they came to Hanover?

There are two competing theories among Winn family history researchers about the origins of the Hanover Winns. Please keep in mind that both theories are speculative, which is why we are calling them “theories.” If a statement in the remainer of this article has documentary proof, the statement has a footnote containing a citation to a source. If there is not a citation to a source, then the statement is speculative. Following the principle of “belt AND suspenders” (meaning you can never have too many safeguards), I will put FACTS in regular typeface, like this. I will put speculation in italics.

As a wise distant cousin likes to say: family history without proof is fiction. PERIOD. If you claim you were descended from President George Washington, that’s fine. But please be aware that Washington had no children with his wife Martha Dandridge Custis, so your DAR application will be a bit tricky.

Here are the competing speculative Winn theories …

The Gloucester Theory.

The Abingdon Parish Register of Gloucester County records the baptism of Richard Winn, son of John Winn and his wife Elizabeth, in 1704.[4] The Gloucester Theory (this is speculation!) is that the Richard born in 1704 was the same man as the Richard Winn of Hanover County who married Phoebe Wilkes Pledger some time before 1733. According to the Gloucester theory, Richard’s parents John and Elizabeth Winn were the grantors in deed #3, above. John, the elder of the two John Winns in the three deeds, died in Hanover without leaving any record. That is believable, because Hanover probate records prior to 1785 are virtually nonexistent. The younger John Winn, who was the grantor in deed #1 and the witness in deeds #2 and #3, was Richard’s brother. John’s birth wasn’t recorded in the Abingdon Parish register for any one of several plausible reasons.

The Gloucester Theory can’t account for the gap in the records between 1704 and 1733, instead pointing to the state of the Gloucester records and the burned counties between Gloucester and Hanover. The Gloucester Theory would chart the early Gloucester/Hanover Winn family like this:

1 John Winn and wife Elizabeth (maiden name unknown) lived in Abingdon Parish, Gloucester County around the turn of the century. They moved to Hanover County some time before 1733.

2 Richard Winn was baptized in 1704 in Abingdon Parish, Gloucester. He married Phoebe Wilkes Pledger, widow of a Mr. Pledger.

2 John Winn’s birth year is unknown, although he was definitely born by 1712. He was in Hanover county, unmarried by 1733.

As a practical matter, the Gloucester Theory starts with known facts – the Abingdon Parish registry and the Hanover deeds – and simply weaves a plausible story to explain the provable facts. But it is nonetheless speculative. Absent a family Bible or other compelling evidence, it may be impossible to prove this theory. The Gloucester courthouse has burned three times, most recently in 1864. Colonial records for Hanover County are also sparse, and that’s putting it mildly. Records for King & Queen, New Kent, and King William counties (located between Gloucester and Hanover), where the family of John and Elizabeth Winn might have lived in the three decade gap between 1704 and 1733 – assuming the Gloucester Theory is correct – are similarly difficult.[6]

The Middlesex Theory

We don’t have to go far for this theory: just to the north of Gloucester County, across the Piankatank River, to Middlesex County. Christ Church Parish, which had the same boundaries as the county, has these entries for six children of Richard and Sarah Winn:

  1. Mary Winn born 16 Xember 1696-97.
  2. Sarah Winn born 17 January 1698-99
  3. Richard Win, son of Richd and Sarah Win, baptized 28 Sept 1701.
  4. Elizabeth Winn, dau of Richard and Sarah Winn, baptized 18 Apr 1703.
  5. John Winn, son of Richard Win and wife Sarah, baptized 20 Jan 1705.
  6. Jane Winn, dau of Richard and Sarah Winn, baptized 15 Feb 1707.

The Middlesex Theory (this is speculation!) is that the Richard Winn (b. 1701) and John Winn (b. 1704-05) in Middlesex are the same men as the grantors/grantees in Hanover deeds #2 and #3, above. The Middlesex Theory doesn’t account further for Richard, the father of those six children. The last entry I found for Richard in Middlesex (which has quite extensive colonial records) was in 1710, when he served on a jury, so he probably left Middlesex after that.[7] The Middlesex Theory doesn’t attempt to explain the gap between 1710 and 1733. The theory just postulates that Richard and Sarah Winn’s sons Richard and John migrated to Hanover County by 1733. Richard married Phoebe Wilkes Pledger some time before 1733. Also some time before 1733, John Winn married Elizabeth (maiden name unknown). Elizabeth died, and then John married as wife #2 Mary Pledger, who witnessed deeds #2 and #3.

The Middlesex Theory would produce this chart:

1 Richard Winn and wife Sarah ______ who lived in Christ Church Parish, Middlesex County, in the late 1690s.

2 Richard Winn b. 1701 m. Phoebe Wilkes Pledger before 1733.

2 John Winn b. 1705 m. #1 Elizabeth LNU before 1733 and m. #2 Mary Pledger after 1733.

There is one glaring problem with the Middlesex Theory that I wish someone could explain satisfactorily. Who is the second John Winn who witnessed deeds #2 and #3? If you’re going to weave a credible story, you really need to account for all the players.

The Middlesex Theory says that Richard (grantor in deed #2) was born in 1701, and John (with wife Elizabeth, grantor in deed #3) was born in 1705. That would make Richard and John about 32 and 28, respectively, when they executed those 1733 deeds. Neither one of them was old enough in 1733 to have a son John who was able to write, much less witness a deed. There is nothing speculative about that: the second John Winn was unquestionably also of legal age.

The options are narrowing, aren’t they? The second John Winn was definitely not a son of either Richard and Phoebe or John and Elizabeth. The second John Winn wasn’t the father of Richard m. Phoebe and John m. Elizabeth & Mary, since the Middlesex theory identifies a Richard as the father of Richard and John father. But the second John was clearly family.

Cousin seems to be the last remaining reasonable possibility. Oh, boy … where did he come from? And where did he go? There was only one Winn family in the Christ Church Parish register and in Middlesex County. Somebody out there has to have some idea.

Which of the two theories is your pet? The vast majority of Winn researchers have adopted the Middlesex Theory. In fact, I can no longer find anyone with a tree posted on who still claims descent from John and Elizabeth of Abingdon Parish, but my search skills stink. There were a few around on the web at one time. I suppose they have all been shouted down by the Middlesex Theory advocates.

In that regard, some Winn researchers state the Middlesex Theory as fact. This ought to merit the genealogical equivalent of the death penalty, or at least permanent loss of credibility.

Unfortunately, YDNA doesn’t help, if you look closely at the DNA results. There are (as nearly as I can tell) two participants in the Winn Family DNA Project who claim descent from Middlesex Winns. The others who are their matches apparently claim only provable ancestry (and good for them!), but not back to Middlesex. What is the proof of those claiming descent from Richard and Sarah of Middlesex? Gee, it would be nice to know, wouldn’t it?

In my own family tree software, my Winn line ends with Richard and Phoebe Wilkes Pledger Winn of Hanover. The Gloucester Theory seems to me to weave a better story in terms of reconciling all the known facts. But … it’s still just speculation. Call me prissy and old-fashioned. Guilty!

I’m hoping somebody who reads this will post a comment with more evidence one way or another.

At least one compiled family history (Jarvis-Winn) has more to say on the Hanover family. It was written by a pair of descendants of John Winn of Hanover County. The authors were both born in the 1800s, and the evidence they compiled appears to have been substantial. I’ll get to that in the next post on the Winns, in which I’ll share a picture of a fabulous oil painting sent to me by my friend and cousin Sandra Wynne Irwin.

* * * * * * *

[1] Rosalie Edith Davis, Hanover County, Virginia Court Records 1733-1735: Deeds, Wills and Inventories (1979), at 19.

[2] Id. at 13-14.

[3] Id. at 16-18.

[4] Robert W. Robins, The Register of Abingdon Parish, Gloucester County, VA 1677-1780 (Arlington, VA: Honforn House, 1981).

[5] Here is a link to part 2, a link to part 3, a link to part 4, and a link to part 5. Whew! If you click on all of those, you will have opened a bunch of tabs. <grin>

[6] New Kent county deed books begin in 1865. King & Queen County deed books begin in 1864. The King William County clerk’s office burned in 1885 and most records were destroyed. This is where family lines go to become unprovable.

[7] Ruth and Sam Sparacio, Middlesex County, Virginia Order Book 1708 – 1710 (McLean, VA: The Antient Press, 1998), abstract of Order Book 4: 290.

11 thoughts on “Virginia Winns Part 6: Competing Theories About the Hanover Winns”

  1. Hi, Robin.

    My name is Jessica Richmond and I happen to be a direct descendant of Edward Buxton Lindsey myself, or so I thought. Have you found any information to back this lineage up? I am a little confused when looking at my own line and I am hoping you can help.

    According to my tree, and to many others on, my lineage is as follows:

    William Lindsey (1767-1817) MARRIED Mary Polly ? (1776-1878)


    Edward Buxton Lindsey (1797-1872) MARRIED Rachel Murphy (1803-1830)


    Rachel Lindsey (1830-1867) MARRIED John Jefferson Lowry (1823-1896)


    John Harvey Lee Lowry (1864-1950) MARRIED Mary Luellar Waters (1869-1948)

    1. Hi, Jessica! I’m betting you are descended from Edward Lindsey of Benton County, Tennessee who m. Rachel Murphy. Is that right? Yes, I have a ton of information to back my own lineage up.

      I’m also going to bet that a Benton county tombstone erected by a descendant is the only proof any of the trees on have that the Edward Lindsey who married Rachel Murphy had a middle name of BUXTON.

      Long story. Let me know whether you’re from the Benton county line and what you find about Edward’s middle name. And I’ll send you a long email.


  2. Thank you once again for this valuable contribution to all of us Winn researchers, Robin. It’s a model genealogical article, cogently argued, clear, logical — almost like a case a well-trained attorney might make. 🙂

    I appreciate what you do here, because I have dealt with this very same problem with my OTHER Hanover County families. So I know what it’s like to take those very sparse records and try, painstakingly but with far too little information, to extend a Hanover County line in this period back beyond that burnt-records county.

    The line I’ve probably tussled with most there is my Thomson line. I had to tussle with it because it had become so tangled, with five different men named Thomas Thomson (various spellings of the surname) living in Hanover at the same time, who had to be separated by estate records, tax records, land records, court records, vestry records — any scraps of information I could find.

    Once I had separated my Thomas Thomson from the others and began to try to figure out something about his past, there were some strong clues that the cluster of families connecting to him in Hanover records had roots in New Kent County, Virginia. But nothing in the way of substantial evidence to form a clear link between him and Thomsons in New Kent from early in the colonial period.

    All this is to say that I know how difficult this is, from my own experience working on a parallel Hanover project — and I’m all the more grateful to you for that reason.

  3. Bravo!!! Thank you so much ! I’m still reading and rereading the Virginia Winn post.
    I wish I knew more about the Lindsey clan of Benton, TN . My ancestor John Winn b 179? in SC was in first Stewart Co, 1820 Henry Co, 1830 there after in Benton Co, TN 1840 he never moved that I know of the county line just changed ( he did move after he remarried after in 1846 but stayed in the same county and area)he was a neighbor to a John Lindsey for many many years and I always thought there may have been a connection but I never found one. Later generations of my Winn family did marry into the this Benton Co, TN Lindsey family.

  4. Robin, I only recently was able to connect my ancestry to the Winns, using circumstantial evidence showing Medkip (Medcalf) Thompson’s wife Judith to be a probable daughter of Michael Holland and Phebe Winn in Amelia County. So, I was thrilled to find your well reasoned and documented arguments about the Winn Family. You have not only saved me an incredible amount of work (except a little fact checking), but you have saved me from pursuing what are clearly some dead ends. We all need to approach this work with healthy skepticism and a willingness to avoid adopting what is mere consensus.

    By the way, although I actually find your exposition of the Glouchester Theory compelling, I will follow your lead and leave the origin of Richard Winn of Hanover unproved.


    1. Eric, thanks for letting me hear from you! I haven’t tried to track Phebe Winn Holland’s children. Would you be willing to share their names/dates/spouses?

      Also, I found this deposition testimony in my Amelia Co. database. Another Winn researcher sent it to me years ago. I have never seen the original, so it definitely falls in the category of needing a little fact checking to make sure it’s genuine. If it is, you’ve probably already seen it, but … just in case … here ’tis:

      Deposition executed 3 Jan 1764 by John Nance, presumably to prove gifts of slaves to children of Michael Holland:

      “About 8 or 9 years ago [1755-1756], I heard my son Giles say that Michael Holland had given his daughter Mary, two Negroes, Patt & Nann. After that time, I heard Michael Holland say that he had given his daughter Mary the same 2 Negroes, & sometime since the wife of said Holland was apprehensive that no gift should be good unless it was recorded. Holland’s wife wanted one r_____ to her brother Winn to have the above gift recorded in court. I spoke to the said Winn concerning that affair & he promised he would have it done. I told Mrs. Holland what Mr. Winn had said, and she asked her husband Michael if he was willing that the gift should be recorded & the said Holland agreed to it in Aug. or Sep, 1762. But 5 weeks before Michael Holland’s death, he, Michael Holland, came to my house, & as we sat at dinner in the yard, he said what a fine thing it was to have a small family, for his was so large that he wished that his children were old enough to go for themselves. I, getting up from the table, went into the house. As I stepped out again, I heard my daughter, Elizabeth, say to Michael Holland, what you intend the blacks shall go to the whites. Yes, said Michael Holland, I have given my daughter Mary 2 & I intend to give Joseph 2. I said to Michael, you don’t divide them equally, you should have given Mary a girl & boy and Joe a girl & boy. No, said Michael, Mary seemed to make choice of them 2 & them I have given her.” Signed John Nance, Jan 3, 1764

      Reportedly at Amelia Deed Book 8: 314.

      Please let me know if you break the code on the origin of Richard Winn of Hanover!


      1. Yes Robin, I have seen this deposition.

        Michael Holland died intestate and although Phebe Winn maintained her dower rights, Joseph, his first-born-son son, was heir-at-law for all his real property. Under colonial inheritance law, however, the right of primogeniture, because of an intestate death, applied only to real property. Joseph had to share the value of his father’s (Michael) personal property with the other siblings . Thus sibling Mary sued to record her existing ownership of two slaves to avoid diluting her total inheritance and Joseph also sued to record ownership of another two slaves to minimize the number of slaves in Michael’s estate and thus the value of the estate that he had to share with his siblings.

        Michael Holland and Phebe Winns children:
        Joseph b. abt. 1745 d. Aug 16, 1779, spouse Mary (maiden name unknown)
        Mary b. abt 1746
        Keturah (probable) b. abt 1747
        Judith (probable) b. abt 1748 d, 1795, spouse Medkip (Medcalf) Thompson b. 1748 d. abt Oct 17, 1789
        George b. Bef. 1749
        Zachariah Holland (probable) b. abt 1750

        Interestingly, George Holland and Medkip Thompson were both separately ordered bound out in 1763, Medkip because he was a poor orphan, and they both ended up in the household of a William Sneed — slave patroller/slave catcher. I think this is how Medkip became enmeshed in the Holland family.


        1. Eric, thanks for sharing the info about the Hollands.

          I need to go back to Henning’s, apparently, because I thought that Virginia had abandoned the common law of primogeniture and enacted its own “Intestate
          Descent and Distribution” statute by the mid 18th century as to both realty and personalty. Apparently my memory is wrong. I should probably do a blog piece about the evolution of descent and distribution laws, but … geez … I got OUT of the law business! Hahahaha …

          Interesting family, the Hollands. Thanks again for sharing.


          1. Robin,

            I just thought of my previous post when I came came across this essay regarding primogeniture in the southern states ( which includes this particular reference and source for Virginia.
            “In Virginia:
            In Virginia (VA) the entail was abolished in 1776; however, primogeniture was not eliminated in VA until 1785. The VA law, unlike the NC law of 1784, provided for equal sharing of real property among all the heirs – both male and female. [See C. Ray Keim, Primogeniture and Entail in Colonial Virginia, William and Mary Quarterly, Volume XXV, No. 4 (October 1968), Pages 550-551]”

            So, until 1785, if someone died intestate in Virginia, his real property (land) went to his first born son, and his personal property (stuff, including slaves) was split among all his heirs (male and female).


  5. Hello Robin, Just found your blog and am devouring every Winn article. I would like to request that if the Winn Surname Project has proof that Sub Group K and Sub Group M are not related then their reasoning should be explained. I ran a sort on 111 markers, which is the most accurate and could not find the deviations between the K and M subgroups. Which STR marker is different? Which chromosome is mismatched? If theories are to be made using DNA then more information should be provided. After all, don’t we require sources for our paper trails? I have my father’s Ydna at the Gresham Surname Project on FTDNA and it is very interesting, but only if it is backed up by a paper trail. I uploaded his raw data to GEDMATCH and asked another close Gresham dna match to do the same for more in depth comparisons. Winn descendants can do the same. Either we need a documented male descendant of the Puleston Winn line still living in Wales to compare to or a direct male descendant of Robert of Canterbury still living in England to use for comparison to our Sub Groups M and K. Direct female descendants can have their Ydna extracted on GEDMATCH to use in lieu of a male Y descendant. Your wonderful logical analytical mind is a joy! I am grateful for your research on the Daniel Winn line..

  6. I am researching the Zachariah Johnston b. 1742 in Augusta County. I am looking for two of his missing sons, William Johnston born 1766 and George Johnston 1777. George moved to Lexington and disappeared. Anywho, I came across a William Johnston b. 1766 at Cave Hill Cemetery in Lexington. He was married to an Elizabeth Winn, with a son named Dr. James Chew Johnston (same crypt). Anyhow, there are 14 other Winns there: Arminta Winn d. 1856, Elizabeth Winn B/d unknown, etc. Thought it might be helpful to someone. The Chew connection came from William Johnston’s will. It is correct. Dr. James Chew Johnston was the only child.

    James Chew may be Elizabeth Winn’s maternal grandfather. The 1700 Johnstons always named in that order. With Chew as a middle name, this is not the Zachariah Johnston line, more than likely the William Johnston and Ann “Nan” Chew line. I hope this is helpful to someone.

    By the way, was Jessamine County KY named after the Winn’s Jessamine Plantation?


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