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 Ancestry.com, 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:
- 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.
- 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.
- 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.
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. 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.
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:
- Mary Winn born 16 Xember 1696-97.
- Sarah Winn born 17 January 1698-99
- Richard Win, son of Richd and Sarah Win, baptized 28 Sept 1701.
- Elizabeth Winn, dau of Richard and Sarah Winn, baptized 18 Apr 1703.
- John Winn, son of Richard Win and wife Sarah, baptized 20 Jan 1705.
- 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. 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 Ancestry.com 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.
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 Rosalie Edith Davis, Hanover County, Virginia Court Records 1733-1735: Deeds, Wills and Inventories (1979), at 19.
 Id. at 13-14.
 Id. at 16-18.
 Robert W. Robins, The Register of Abingdon Parish, Gloucester County, VA 1677-1780 (Arlington, VA: Honforn House, 1981).
 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.
 Ruth and Sam Sparacio, Middlesex County, Virginia Order Book 1708 – 1710 (McLean, VA: The Antient Press, 1998), abstract of Order Book 4: 290.