Virginia Winn Series Part 7: Portrait of Mrs. John Winn of Hanover County

My friend and cousin Sandra Wynne Irwin sent to me an image of this wonderful oil painting.

She’s absolutely charming, isn’t she, despite the poor quality of this reproduction?

The Smithsonian catalog identifies her as Mrs. John Winn of Hanover County, Virginia. The portrait was painted during 1735–1740. The artist reportedly lived in Hanover at one time during that period (more on that below). Thus, this lovely woman’s husband was almost certainly one of the two John Winns who appeared in two 1733 Hanover County deeds. If you’ve forgotten the two frustrating John Winns in those deeds, check out Part 6 of this Winn series.

The conventional wisdom is that Mrs. Winn’s maiden name was Mary Pledger, per the Middlesex Theory (see also Part 6). That’s what you will consistently find online, although there are still a few holdouts who believe that Mary Pledger married John Winn of Amelia County as his first wife. He was a son of Richard and Phoebe Winn of Hanover County: Richard, according to the Middlesex Theory, was John Winn’s brother.

None of the trees I have looked at offer any evidence that Mary Pledger married John Winn. So far as I know, the only evidence is the fact that she witnessed those two John Winn/Richard Winn deeds in Hanover. That’s good, so far as it goes, but … is that all we’ve got?

Undeterred by my inability to uncover conventional evidence, I have been deep-diving into an odd combination of sources, including the Smithsonian American Art Museum Catalog, an old issue of The Virginia Magazine of History and Biography, and a compiled family history writen in 1932 titled Ancestors and Descendants of John Quarles Winn and His Wife Mary Liscome Jarvis. All in an effort to find proof of Mrs. Winn’s identity. No luck, but it was fun looking, so I’m sharing the deep dive.

The Smithsonian American Art Museum Catalog says this  in relevant part about the painting

“Portrait of Mrs. John Winn of Jassamine Lawn, Hanover County, Virginia, (painting).

Artist:                     Charles Bridges, active circa 1735-1740, painter.

Dates:                      Circa 1738.

Medium:                Oil on canvas

Dimenensions:  49 x 40 (inches)

Subject:                  Portrait female – Winn, John, Mrs. (Mary Pledger) – full length

Owner:                    Anonymous Collection

Provenance:       Formerly in the collect of the family of Mrs. John Winn; Girard Burwell Lambert, Millwood, VA until 1948; Mr. and Mrs. Frank E. Christopher, Millwood, VA, 1948; Sotheby Parke Bernet, New York, NY Sale (Sept. 18, 1976), lot 279; Anonymous Collection; Sotheby Parke Bernet, New York, NY Sale 4999 (Jan. 1983), lot 182; Craig & Tarlton, Raleigh, North Carolina until Nov. 5, 1985; Christie’s, New York, NY Sale Raleigh-6034 (Nov. 5-6, 1985), lot 261

Remarks:            Mary was the second wife of John Winn (baptised Jan. 20, 1707-died ca. 1789), a substantial landowner and planter in Virginia. Mary and John married in 1738 and lived on his Hanover County plantation “Jessamine Lawn.” They had five children, the eldest of whom was born ca. 1749. This portrait of Mary Winn is believed to be her wedding portrait painted in 1738. In 1738, the artist Charles Bridges also lived in Hanover County, Virginia. The painting descended through the family to Girard Burwell Lambert, “Carter Hall,” Millwood, Virginia, the great-great-great-grandson of the sitter. Mr. and Mrs. Frank E. Christopher acquired the painting in 1948 when they purchased “Carter Hall.” The painting was listed as attributed to Charles Bridges in both the 1983 Sotheby Parke Bernet sale catalog and in the 1985 Christie’s sale catalog. IAP files contain additional information supporting Charles Bridges as the artist of the portrait.

References:      Sotheby Parke Bernet, Sale 499 (Jan. 27, 1983), lot 182;m Christie’s, Sale Raleigh-6034 (Nov. 5-6, 1985), lot 261; Winn, B. Meredith, Jr., 2011

The information offered in “remarks” obviously echoes the Middlesex Theory, identifying Mary, the subject of the portrait, as nèe Pledger, and as the second wife of John Winn of Hanover (see, again, Part 6).

“References” shows the Smithsonian’s sources. They include B. (Bernard) Meredith Winn Jr., who provided information to the Smithsonian in (apparently) 2011. Mr. Winn is presumably a descendant of John and Mary Winn of Hanover, or is surely from a related line. If he has taken a YDNA test, he is probably a decent match for the lines of Col. Thomas Winn and Daniel Winn of Lunenburg, John Winn of Amelia, and Minor Winn of Fauquier. I do wish he would upgrade his test to “Big Y” so all of his distant cousins, myself included, could pinpoint the location in the U.K. from which the Winns migrated. I especially wish he would share any evidence he might have about the Hanover Winns circa 1730–1789, because he might have something besides the Christ Church parish register and those three darn Hanover deeds. Perhaps he has a family Bible, or at least a family oral tradition.

I don’t have the nerve to track down someone who is probably about my age (i.e., old and increasingly cranky) and ask him to produce some proof about the identity of his ancestress. Even the most hardcore genealogist has her limits.

Please just keep in mind that what the Smithsonian Catalog says isn’t evidence of Mary Winn’s maiden name.

There is another Winn compiled family history which deems the identity of Mrs. John Winn unproved. Otherwise, it shares the Middlesex Theory, tracing John Winn’s ancestry to Richard and Sarah Winn of Christ Church Parish, Middlesex County. For that view, see Ancestors and Descendants of John Quarles Winn and His Wife Mary Liscome Jarvis (Baltimore: Lord Baltimore Press, 1932). The authors were David Watson Winn (1857-1926) and Elizabeth Jarvis Winn (1891-1965). Note that both of these authors were a century closer to these Winns than we are, and they had considerable documentary evidence.

The Jarvin/Winn book doesn’t identify the maiden name of Mary Winn, wife of John Winn of Jessamine Lawn, Hanover County.

The entire book can be downloaded here. Do read the Foreword, which talks about their remarkable sources. At one time, they apparently had an opinion written by John Marshall, the first Chief Justice of the Supreme Court. See, e.g., Marbury v. Madison, a famous case I had to brief about 10 times in law school.

Finally, there is an interesting article about Mrs. John Winn’s portrait and the artist in a 1952 issue of The Virginia Magazine of History and Biography[1]. It offers no opinion on Mrs. Winn’s identity, which is understandable: the article is primarily about the artist, Charles Bridges. Here is a link to the article.

It is a lonnnnggg read. It has reproductions of a number of paintings by the artist, mostly members of the Byrd family, which are fun. Here, edited somewhat, is what The Virginia Magazine has to say about the portrait of Mrs. John Winn. It also echoes the Middlesex Theory, except it does not identify Mrs. Winn as Mary Pledger, probably because the source for the family information was the Jarvis/Winn compiled history.

“Mrs. John Winn

Subject: The portrait is said to represent Mary, second wife of John Winn, of “Jessamine Lawn,” Hanover County. He was baptized Jan. 20, 1705, died c. 1789. The date of their marriage is unknown, but they had five children, the eldest born in 1749 or earlier. (See Ancestors and Descendants of John Quarles Winn, Ed. D. W. Winn, Baltimore, 1932).

The identification may perhaps be correct, although there seem to be no documents supporting it. If correct, the subject may have been painted as early as 1740, before her marriage, since she appears as a young woman in her early twenties and it is not certain that she had any children before 1740.

Description: The subject is a pleasing young woman shown standing full-front against a dark background beside a table on which her right hand rests … [t]he picture has been largely repainted, so that the costume does not show Bridges’ technique, but the tilt of the head and the rendition of the features so much resemble the painting of the heads of the young women of the Byrd family so as to make the attribution of this portrait to Bridges seem at least possible.

Owner: Mr. Frank E. Christopher, Carter Hall, Millwood, Va. The portrait was acquired before 1938 by Mr. Gerard B. Lambert who then owned Carter Hall, and was sold with the residence to Mr. Christopher in 1948. Its earlier provenance is not recorded.”

The author of the Virginia Magazine history was writing in the early 1950s, so the “Owner” information is clearly out of date.

In any event, I hoped you enjoyed a break from the usual post at this blog! Can’t beat a fabulous oil painting …

And that does it for me with the Winns, unless I recover sufficiently to elaborate on some of the Lunenburg or Amelia Winns, a crowd that doesn’t require so many speculative theories!!!

* * * * * * * * * *

[1] Henry Wilder Foote, “Charles Bridges: “Sergeant-Painter of Virginia” 1735-1740,” The Virginia Magazine of History and Biography 60, no. 1 (1952), at 3-55.

22 thoughts on “Virginia Winn Series Part 7: Portrait of Mrs. John Winn of Hanover County”

  1. Robin,

    Virginia Winn part 7
    The research that you have done on these early Virginia Winns is a gift to all that are researching the Winn family. Thank you ? !

    1. Hopefully, some more Winn researchers will comment and share their family Bibles or other proof. You know there has GOT to be more “out there” than is available to us average researchers who only have the county records. Glad you’ve enjoyed the articles, and thank you again for sending me that wonderful portrait and for sharing with me your extensive knowledge of these families. xoxoxox

  2. Great research. I am a descendant on my mothers side of Daniel Winn and John Winn who you identify as John 1795. I have done considerable research and may have some info tom help you. Please contact me by EMAIL.

  3. I am disappointed that this is not the wife of my John Winn b. CA 1732 in Hanover Co VA to Richard Winn Jr. the older brother of this John Winn. I have copies of the Middlesex County Church records. However these records are great. I’ll take what I can get. My mother was a Winn and the only grand child of her Winn Line. I am desperately searching for an obituary for John Winn Sr. that I mentioned above. I am trying to prove he was the John Winn of Amelia Co who served in the house of Burgess and the Delegate to the Statehood Conventions in VA. I believe I have proof, but an obit that lists his service and his family would be great. Anyone have a membership to Or access at a nearby library? My Winn Line: Richard Winn Jr.1701; John Winn 1732-1781 Amelia Co VA; John Winn 1759 VA-1838 OH; Douglas I. Winn 1788 KY-1853 MO; Thomas R. Winn 1819 OH-1889 MO; Napoleon S. Winn 1843 MO-1918 MO; Lloyd A. Winn 1891 MO-1974MO; Margaret B. Winn; Me

  4. I wanted to comment, on the comment, that Mary Wilkes Pledger might be the wife of John Winn of Amelia Co VA. He was too young to have married her especially as a first wife. Being born Ca. 1732 and the painting was done 1735-1740 John Winn of Amelia Co would have been 3 to 8 years old! This is not likely his wife. His Uncle John Winn of Hanover County where the painting would have been done would have been 30 to 35 years old being born to Richard Sr. in 1705. John Winn Jr. of Hanover Co clearly married Mary Bowles according to the John Winn Jr. Bible. I have a copy of the original and the transcript that was published in the Hanover Co Historical Society bulletin. At any rate John Jr. of Hanover would not have been born yet, nor John Jr. of Amelia Co either.

    1. I am trying to verify my deceased brother’s research. I have been searching for information on John Winn and Mary Bowles as he has identified them as you stated but only mentions a family Bible in Elk Mtn VA ancestor. Other than his mention, yours is the first One I’ve come across online. I am wondering if you would be willing to share the information you have obtained on this lineage? Let me add that my only resource is via the Internet as I am homebound (totally disabled) which eliminates any travel to obtain documentation. I would be happy to send you email information if you are willing to share your information. Let me thank you in advance for your consideration. Deborah Winn

  5. I don’t believe that you’ve mentioned this, but if you have I apologize for not discovering it in your blog, yet…
    Anyway, I am wondering if you, or anyone else reading this blog, might have run across an Ann Winn who married William Webber III on 1 August 1764 in Goochland County, Viriginia. The marriage is recorded in the Douglas Register. The family seems to have resided in St. James Northam Parish, where William Webber died in August 1794. William Webber III and his wife Ann Winn had at least the following children: Philip (names for William Webber III’s father), Benjamin, John, Mary , Keturah, Susannah Winn, Charles, William IV, and Archer. I’ve also seen a son named Archibald attached to this family, but it’s possible that Archer and Archibald may be the same person. Ann Winn Weber is sometimes placed as a daughter of John Winn and Mary Pledger, but my impression is that their daughter Ann was married to Nathaniel Holman and no one else. Any information, thoughts, theories, or suggestions on who this Ann Winn was and where she fits in the Winn family would be much appreciated. Thanks.

    1. Jeff, I haven’t mentioned the Ann Winn m. William Webber III in 1764. I found only two brief mentions of Winns in Goochland County records (although I evidently failed to look at marriage records). (1) Richard, who witnessed a 1739 deed, Robert Wade of Hanover, grantor, to ________ (can’t read my notes). That deed may well have been and probably was executed in Hanover, since that is where the grantor lived. So, as you know, did Richard Winn m. Mary (possibly Wilkes) Pledger. (2) John and his wife Mary appeared in three early Goochland deeds. John purchased a tract of 400A which was right on the Goochland/Hanover County line in 1735/36 from Humphrey Parish, no known connection to the Winns. John conveyed the same tract back to Parish in May 1738; his wife Mary Winn released dower. In 1739/40, John patented another 400A Goochland tract on Byrd’s Creek, north side of the James, which he promptly sold to John Horn, no known connection. Mary was again named in relinquishment of dower. In the three conveyances, John is described as “of” Goochland, Henrico, or Hanover County. These are probably all the same man. Perhaps those deeds are the basis for placing Ann as a daughter of John Winn and Mary?

      Will you please let me know what you learn? I haven’t spent any significant time on the Hanover Winns save for the 1730s deeds among Richard and the two John Winns that continue to puzzle me.

      Good luck!

  6. I am B. Meredith Winn, Jr., and I live about 5 miles from Jessamine Lawn. Some things to notice about John: There appear to be 3 Johns in a row each having married a Mary. I am in the descendancy line from Hezekiah who had Minor, who had the second Hezekiah (my great great Grandfather). I have “proofs” that the Hezekiahs are grandfather/grandson in my line. (you may laugh at my use of the word “proof”.My grandmother (born shortly after the civil war) used to say “There were two Hezekiah’s.” Her stories fit perfectly. My proof of Mary Pledger being related to the painting was this: Her grandson named his firstborn son “Charles Bridges Winn.” about 1807

    1. Bernard, thank you for the information! I would call your “proofs” “evidence,” but would agree that they “prove” your Hezekiahs and Mary Pledger! Now I need to rework that article to include your information. Glad to hear from you!
      Robin (descended from Richard and Phoebe Wilkes Pledger Winn of Hanover Co.)

    2. Hello Mr. Winn,
      I have been researching my family (Snead, Sneed, Sneyd, Sneyde) history since my father passed in 2020. I came across an extensive family tree on which lists my great-great-great-great-great-great grandmother as Jane Winn, wife of John Snead, as well as the daughter of Mary Pledger and John Winn. It also lists Jane as the sister of Hezekiah, that you mention. This is all from just a few weeks of research online, so I have no “proof” or even know how accurate this family tree is.
      Any information you have, if you ever get time, I’d love to look at it and learn more.

      If accurate, I’d say we are (very, very) distant cousins. I have not read much about Jessamine Lawn, but I came across a transcript of a will from 1793 that was written by John Snead (Jno. Snead is apparently how it was signed) that mentions Stonyrun, land he gave to his son Augustine Snead. The end of the transcript says the following: “June 19, 2018 abstracted from photocopy of copy signed by Jno Snead “I believe this is a true copy except the words is spelled Some Better” and a transcription written out by the grandfather of Susan Clardy who was in possesion of both in 1997; by Mary Herzog”.

      I don’t know who Susan Clardy or Mary Herzog are, but would be amazing to see a copy of that will. The names listed in the will match names of John and Jane’s children on the family tree I am looking at.

      Thanks to everyone for all the information I have been able to read through on this blog. If anyone ever has anything of interest or anything to share, my email is

      Colton Thomas Snead (named after my great grandfather, Thomas Kendrick “TK” Snead)

      1. Hello Colton,

        I just looked at this website today. Bernard Winn died in September 2020. I had communicated with him by email about our Winn relatives; specifically about Winn’s Baptist Church which is on donated Winn property. Bernard was my third cousin. I am confused about the relationship of the “John Winns”. My father was also a John Winn. Would like to know more about the Winn DNA tests. I know that we are Poleston Winns.

    3. My husband is a descendant of John Winn and Mary Pledger. You mention that you live 5 miles from Jessamine Lawn, does the plantation home still exist? If so, are there any pictures of the structure?
      Thank you. Audrey Parkinson

      1. Audrey, I saw you shown as a new subscriber this morning. I was going to send you an email saying “welcome” and asking whether you are a Winn, Willis, or Rankin (the most frequent followers) — but you just answered that question! In my experience, people rarely read the comments. With your permission, I will try to hook you up with Bernard via private email if he doesn’t respond in a few days.

  7. I am in possession of a copy of the Winn Bible that belong to John Winn Jr. of Hanover who married Mary Bolling. If anyone else want this, send me an email: I have a transcription and a digital copy of the original.

    Perhaps someone has found the graves of John Winn Sr. of Amelia County and his wife Susanna Irby. If anyone knows of a portrait of either one or a family Bible for these two please let me know. I have been accepted into the SAR on them with an acceptable proof and I have found a 3 generation document that ties the Father to his son John Winn & Myrtilla and to his daughter Myrtilla and his son Douglas Irby Winn and John Winn Jr. (III). Also maybe someone has a document that lists a middle name for these two as Joseph? This was being used without proof to my knowledge.

  8. I might add that the three generation document was a suit that was filed by Grand daugher, Myrtilla, against her brother, Douglas Irby Winn, who was the executor of his grandmother’s estate when she left it not to her son John Winn Jr., but his children, Susanna’s grand children. Myrtilla who suffered injuries from being thrown from a horse sued her brother in probate court for her share. She one the suite, but died from her injuries before she could collect. Thus the document ties 3 generations together across three states: Virginia, Kentucky, and Ohio.

  9. By the way, that should have been won the suit. By the way, I write this on the anniversary of my Grandmother Lydia Paxton Blackburn Winn’s birthday. Should would be 102 years old today!

  10. Robin

    I don’t believe that we ever got to connect

    This is Chris Winn, I also competed a big Y about 2 years ago and have made a lot of connections (including winn’s in LA from the 1800’s)

    I really would like to connect when you can.


    Let’s connect and I’ll share what I have with you, I’d love to know the connection.


  11. The name John Winn was very popular in Colonial Times and afterwards. I have yet to see any middle names for these early John Winns. The John Winn of Hanover County was related to the John Winn of Amelia County. The John Winn of Hanover County sent his child John Winn to study law, etc. with the John Winn of Amelia County. This is proved by the Tithe Tax Rolls. The cousin appears in the tax rolls when he first turns 16? and then disappears and then a John Winn Jr. reappears when his own son turns 16.

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