The issues in this post are either uncontroversial or I just don’t know the answer. This is a humbling thing to admit, but good for the soul. Let’s jump to the bottom line(s). Whatever evidence is available follows this list, if you like that kind of thing.
- Phoebe Pledger, a widow, definitely married Richard Winn of Hanover County before early 1733. The conventional wisdom says that Richard moved to either Amelia County or Caroline County, or he may have stayed in Hanover. The answer is uncertain.
- Phoebe was almost certainly a daughter of Joseph and Elizabeth Wilkes of New Kent and Hanover counties.
- The identity of Phoebe’s husband before she married Richard Winn, Mr. Pledger, is tougher. Some researchers believe her husband was Joseph Pledger of Abingdon Parish, Gloucester Co. The slender Pledger evidence is interesting but inconclusive.
- Was Phoebe the mother of all Richard’s children, or did he have a prior wife? If there is evidence of an earlier wife, I haven’t found it. For a discussion of the siblings – Col. Thomas Winn and Daniel Winn of Lunenburg, and Phoebe Winn Holland, John Winn, and Susanna Winn Irby of Amelia, as well as (perhaps) Samuel Winn the scoundrel, see Part 2, Part 3, and Part 4.
Now on to the proof … or lack thereof.
Phoebe Pledger, widow, married Richard Winn by 1733.
This one is a piece of cake. Here’s the evidence that Phoebe was married to a Mr. Pledger and that she subsequently married Richard Winn. It’s as solid as proof can get, especially in a burned county like Hanover where surviving 18th-century records are scarce as hen’s teeth.
On 19 and 20 Jan 1733, Richard Winn and his wife Phebe of St. Paul’s Parish, Hanover, executed deeds of lease and release to John Winn, also of Hanover, £ 82 for 517 acres with plantation on Chickahominy Swamp in Hanover, purchased from John Hogg of New Kent by Phebe in her widowhood by the name Phebe Pledger. Witnessed by John Winn, Ann Wheeler, and Mary Pledger.
For future reference, note that there are two John Winns in this deed – the grantee and a witness. Also a witness Mary Pledger.
Did Richard and Phoebe Pledger Winn stay in Hanover? Or did they move to Amelia or Caroline county?
The odds are virtually nil that Richard moved to Amelia County. In a deed identifying him as Richard Winn “of Hanover,” he bought some land in Amelia County in 1744. He never lived on it, because his tithables continued to appear in the Amelia County tax lists with the designation “Richard Winn’s list” or “Richard Winn’s Quarter.” “List” and “Quarter” both mean that Richard owned land and had tithables living on the property, although he didn’t reside there himself. Instead, Richard’s son John began appearing on the tax list with Richard’s enslaved persons in 1751. Richard probably died before that date, but not in Amelia. There is no will for him there. He never appeared in an Amelia court order book, served on a jury, or did anything constituting evidence that he was present in Amelia County. The Amelia colonial records are virtually intact. If Richard had lived there, we would not have been able to miss him.
As of November 1744, Richard Winn still lived in Hanover. After that, he did not appear in the St. Paul’s Parish vestry book, which is the primary extant source for that county during the 1740s and 1750s. That suggests that Richard either died or relocated after 1744.
Some Richard Winn was in Caroline County in person by 14 Mar 1745/46, when he acknowledged a deed there. A Richard Winn (the same or a different man? I don’t know) had acquired land in Caroline in 1735; a Minor Winn also appeared in the Caroline records that year. I haven’t yet waded through all the Caroline order books, a tedious business, so I don’t have a good feel for the Caroline Winns.
The Richard Winn who lived in Caroline died there in 1748. His will was witnessed by a Robert Durrett, and Richard Mauldin provided security for the executor. There don’t seem to be any connections between the Durrett, Mauldin and Winn families in Hanover County, but the Hanover records are so sparse that doesn’t prove much. Those two men may have been family, though. Has anyone found any Durrett/Mauldin/Winn connections anywhere? If so, that might be significant evidence about Richard Winn of Caroline.
Richard of Caroline had a son Benjamin, the only child identified by the Caroline records. If Richard of Caroline is the same man as Richard of Hanover, then we could add Benjamin to Richard and Phoebe’s list of probable and possible children. Perhaps someone who reads this has some evidence whether Richard of Hanover is the same man as Richard of Caroline — and will let the rest of us know. I’m still uncertain.
Who were Phebe Pledger Winn’s Parents?
A Hanover agreement is the only evidence of Phoebe’s parents I have found. Here it is:
Court record of 6 Aug 1734, agreement between Joseph Wilks of Blissland Parish, New Kent, planter, to Richard Winn of St. Paul’s Parish, Hanover, planter, £11.8.3 “in consideration of said Richard Winn finding him what land he shall have occasion to work during his natural life (and the life of Elizabeth his wife), which land shall be a part of the tract of land where … said Richard Winn now lives and shall build upon said land all the necessary buildings fit and convenient for him and also in consideration of the said Richard lending to said Joseph ……. slaves ……..etc.” Witnesses: John Bowles, Robert Mosby, John Winn. Proved 7 Nov 1734 by Jno Bowles and John Winn. Joseph Wilks gave £200 bond to perform his obligations, bond witnesed by John Bowles, John Winn, Robert Mosby, and John Winn.
There may be several ways to interpret that agreement. I take it as indicating that Joseph Wilkes was old, Richard and Phoebe were taking care of him and his wife Elizabeth, and the Wilkes were Phoebe’s parents. Other Winn researchers see this agreement as evidence that Joseph Wilkes wife Elizabeth was Richard’s mother, who married Joseph Wilkes after her Winn husband died. Maybe so, although I disagree. The principle of Occam’s Razor suggests that the more complicated explanation is less likely than the more simple one.
The Amelia tax records establish another Wilkes-Winn connection, a plus for Occam’s Razor. Joseph Wilkes and John Wilkes were tithables on the Amelia property of Richard Winn and Richard’s son John at different times, possibly in a capacity as property overseer. I don’t know how they were related to Phoebe, although I imagine they were related in some fashion. John Pledger married Patience Crenshaw, another family with several Winn connections.
I hope by now your interest has been piqued by the fact that there were two men named John Winn who were of legal age in Hanover County in 1733-34. See the 1733 deeds of lease and release (a John Winn party and a John Winn witness) and the Winn-Wilkes agreement (two witnesses named John Winn). Who were the two John Winns? Let’s talk about them in the next Winn post in this series, when we will look at some records for various Winns in Goochland, Henrico, Middlesex, and Gloucester.
Who Was Phoebe Wilkes Pledger’s Husband before Richard Winn?
I don’t know. Some researchers think he was the Joseph Pledger who appeared in the vestry book Abingdon Parish, Gloucester County, when the birth of his daughter Mary was recorded in 1719.
That could be. Susanna Winn Irby, probably Phoebe’s youngest child, was born between 1730 and 1740. It’s possible that Phoebe was also a mother of a child born in 1719. What do you think?
I have scoured records of counties between the York and Rappahanock Rivers for the late 1600s and early 1700s looking for Pledgers – any Pledgers. Here are ALL the records I have found prior to the time a Philip Pledger began regularly appearing in Amelia records:
- 26 Apr 1708 deed for land in York County, John Keene of New Kent to Hon. Daniell Park, witnessed by George Keeling, John Eaton, and Joseph Pledger. Joseph also witnessed Keene’s performance bond.
- 19 Nov 1708 processioning report in the St. Paul’s Parish vestry book, Hanover County: “The lands of Daniel Parke Esqr, Henry Chiles Gent … being made one precinct … Overseers … made this return on the back of yee Ordr, viz. November 19th 1708, … fully Executed … there were prest [sic, present] every of the within mention’d Persons, except Colo Parke; who was represented by Joseph Pledger. Vestry book at 163, Chamberlayne at 209.
- 18 Oct 1719: Mary Pledger, daughter of Joseph Pledger (wife not named) was baptized in Abingdon Parish, Gloucester County, on 18 Oct 1719.
- 19 and 20 Jan 1733, Mary Pledger witnessed the deeds of release between John Winn and Richard Winn.
The Joseph Pledger who witnessed Daniel Parke’s deed in New Kent (where grantor lived) was surely the same man as the Joseph Pledger who represented Col. Parke at the processioning of Parke’s land in Hanover. Is he the same man as Mary Pledger’s father, who lived in Abingdon Parish, Gloucester? Is this one or two Joseph Pledgers in these three records during 1708 – 1719? It’s a fairly limited geographic area, so my gut hunch is that these records were all the same man. Was he Phoebe’s husband? I don’t know.
How about Mary, Joseph’s daughter, born in 1719 … was she the same woman as the Mary Pledger who witnessed the 1733 Hanover deeds conveying Phoebe Pledger Winn’s former land? She would have been only 14 at the time, too young to prove a deed in court. Do we have one or two Mary Pledgers in these limited records? The Mary Pledger who witnessed the deeds was surely related in some fashion to Phoebe.
Many online trees and websites claim that a Mary Pledger married one of the two John Winns of Hanover County. One John Winn in the Goochland/Henrico/Hanover area did have a wife named Mary (more on them later). Somebody out there must have some evidence – something beyond a bare, unsourced claim – about a Mary Pledger marriage to John Winn, right? I’m still looking.
Was Phoebe Wilkes Pledger Winn the Mother of All Richard Winn’s Children?
I don’t know that, either! She was undoubtedly at least the mother of Susannah Winn Irby, born during the 1730s, and Phoebe Winn Holland. Was she also the mother of Col. Thomas, Daniel, and John Winn of Amelia? None of them named a daughter Phoebe, although Daniel, in all fairness, had only one daughter (Marticia). Was Phoebe the mother of Samuel Winn the Scoundrel and Benjamin Winn of Caroline County? I don’t know. If Phoebe was the mother of the Mary Pledger born in Abingdon Parish in 1719, then all of her Winn children were born after 1720. And that’s about all I can say for sure without speculating.
See you on down the road …
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 Rosalie Edith Davis, Hanover County, Virginia Court Records 1733-1735: Deeds, Wills and Inventories (1979), court records at 13-14, deeds of lease and release from Richard and Phebe Winn to John Winn.
 Amelia County Deed Book 2: 82-83, 15 Nov 1744 deed of lease and release from Stith Hardaway to Richard Winn of Hanover County, 388A in fork below Little Nottoway River and Lazaritta Creek adjacent Epes line.
 Family History Library Film 1,902,616, Amelia County tax list for 1746: Richard Winn “list,” 2 slaves, 2 tithes (so the enslaved persons were the only tithables); Amelia county tax list for 1748, Richard Wyns “Quarter,” the rest unreadable; 1749 tax list, Richard Winn’s list, John Wilkes, Harry, and Flowrey(?), 3 tithes (so there is presumably the overseer, John Wilkes, and 2 enslaved persons); 1750, Richard Winn’s list (adjacent Philip Pledger on the tax list), tithables Harry, Florey, Jenny, 3 tithes (enslaved persons only); 1751 tax list for John Winn, 5 tithes, listed with Joseph Wilks, Harry, Flora and Jean. The fact that the same enslaved persons appeared on Richard Winn’s list in 1750 and with John Winn’s in 1751 is powerful evidence that John Winn was a son of Richard.
 See note 2.
 John Frederick Dorman, Caroline County, Virginia Order Book 1740-1746, Part Three, 1744 – 1746, (Washington, D.C.: 1973), abstract of Order Book 1744-46: 577, 14 Mar 1745/46, Richard Winn acknowledged his deed to his son Benjamin Winn.
 John Frederick Dorman, Caroline County, Virginia Order Book 1732-1740, Part Two, 1734/35-1737 (Washington, D.C.: 1966), abstract of Order Book 1732-40 at 300, 13 Jun 1735, Minor Winn was a defendant in a lawsuit (which means he resided in the county); at 316, John Martin and wife Rachel acknolwedged deeds of lease and release to Richard Winn, 14 Nov 1735 (Richard need not have been living there).
 John Frederick Dorman, Caroline County, Virginia Order Book 1746-1754, Part One, 1746/47-1748 (Washington, D.C.: 1968), abstract of Order Book 1746-54: 123, entry of 9 Dec 1748, will of Richard Winn presented by Benjamin Winn, executor, proved by Richard Mauldin who swore he saw Robert Durrett witness the will. Bond by Benjamin Winn, Richard Mauldin was his security. Based solely on the Amelia County tax lists, 1748 might be a bit too early: Richard of Hanover may have still been alive in 1750, when he was taxed in Amelia County. Had the Amelia County tax assessor known that Richard had died, the tithables would have been designated as Richard Winn’s estate.
 See note 6.
 Rosalie Edith Davis, Hanover County, Virginia Court Records 1733-1735: Deeds, Wills and Inventories (1979), abstract of court record of 6 Aug 1734 at pp. 148-49, agreement between Joseph Wilkes of New Kent and Richard Winn of Hanover.
 See note 3.
 See notes 2 and 9.
 Vestry Book of Petsworth Parish, Glouchester County, Virginia 1677 – 1793, transcribed by C. G. Chamberlayne, Richmond, VA, 1933, entry of 18 Oct 1719: Mary, daughter of Joseph Pledger, was baptized.
 See, e.g., Amelia County Deed Book 2: 183, deed dated 18 Jul 1745 from John Ellis to Philip Pledger, for love and affection for Philip who married his daughter Nanny Ellis adjacent Irby. Recall that John Ellis was the father of Sarah Ellis Winn, the unfortunate wife of Samuel Winn the Scoundrel.
 Mary Marshall Brewer, York County, Virginia Land Records 1694 – 1713 (Lewes, Delaware: Colonial Roots, 2006), abstract of York Co. Deeds and Bonds 2: 282.