Hooray! A query via email …
Answer #1: the circumstantial evidence is that Lt. Col. John Winn of Amelia County, Virginia (hereafter “Col. John”) was a son of Richard Winn of Hanover County. Richard’s wife and perhaps John’s mother was Phebe, widow of a Mr. Pledger.
Answer #2: Yes, Amelia John was related to the Winn families of Lunenburg County.
Well. I suppose an explanation and some evidence is in order. Alternatively, we could avoid a lot of footnotes if readers would just accept my version of the facts as readily as people accept unsourced family trees on Ancestry.
I thought not.
For Answer #1, we need to look at records involving Richard Winn of Hanover County. They establish that (1) Richard married Phebe ___ Pledger, (2) he owned land in Amelia County, (3) he didn’t live in Amelia but paid taxes on some enslaved people there, and (4) Col. John subsequently acquired Richard’s tract and the enslaved people, evidently via inheritance.
(1) A 1733 Hanover County lease and release proves Richard Winn’s wife was Phebe, the widow of a Mr. Pledger. We don’t know when Richard and Phebe married, so we can’t be certain that Phebe was the mother of Richard’s children.
(2) In 1744, Richard Winn of Hanover County bought 388 acres in Amelia County in the fork below the Little Nottoway River and Lazaritta Creek. Richard had tithable (taxable) people on that tract in at least 1746, 1748, and 1749, even though he didn’t live in Amelia. In 1749, John Wilke or Wilkes, perhaps Richard’s overseer, was one of his taxables. The two other taxable people with Wilkes were enslaved persons named Harry and Flowrey? The latter name is difficult to read on the film. Turns out it is “Flora,” perhaps pronounced “Flory,” see item (3).
(3) In 1751, the Amelia tax list includes an entry for John (rather than Richard) Winn, with taxables Joseph Wilkes, Harry, Flora, and Jean. Col. John Winn had apparently acquired the tract along with the enslaved people from Richard. There is no Amelia deed for any such purchase. That raises the inference that Col. John acquired the tract and enslaved people via inheritance. Records in Hanover are largely lost, so there is probably no will to be found there.
However, there is other evidence linking Col. John to Hanover. His eldest son Richard Winn was a Revolutionary War soldier whose widow Jane Pincham Winn applied for a pension for his service. Her application file includes the information that Richard’s father was Col. John Winn (identified by that title) who was born in Hanover County, Virginia.
Other facts for the record … Col. John married Susanna Irby, daughter of Charles Irby Sr., in 1754. John was probably born in the early 1720s and died in January 1781. Col. John’s sister Susanna Winn married John Irby (Susanna Irby Winn’s brother) in 1757. Are we dizzy yet? John and Susannah Winn Irby had children named Charles, Lucey, and John. Another sister, Phebe Winn, was the wife of Michael Holland. The Winns and Irbys of Amelia County played a significant role in proving the Amelia-Lunenburg Winn family connection.
Which brings is to Answer #2, Col. John’s relationship to the Lunenburg Winn families.
The Winn DNA project results table does not include a group identified as descendants of Col. John Winn of Amelia. However, there is a group designated “Richard Winn … m. Phebe Pledger, Hanover Co. VA.” If you accept that Col. John was a son of Richard of Hanover with wife Phebe, then the Y-DNA evidence will convince you that Col. John shared a common Winn ancestor with Col. Thomas Winn, Daniel Winn, and John Winn (wife Ann Stone), all of Lunenburg.
Of course, Y-DNA doesn’t identify the nature of their relationships. However, there is compelling circumstantial paper evidence that Col. John of Amelia and Col. Thomas of Lunenburg were brothers. The evidence that Daniel Winn of Lunenberg was another brother is also convincing. I identify five people as children of Richard and (perhaps) Phebe Pledger Winn of Hanover, not necessarily in birth order:
Col. John Winn of Amelia (wife Susanna Irby, daughter of Charles Irby Sr.)
Col. Thomas Winn of Lunenburg (two wives, possibly Miss Bannister and perhaps Sarah Bacon)
Susanna Winn of Amelia (husband John Irby, son of Charles Irby Sr.)
Phebe Winn of Amelia (husband Michael Holland)
Daniel Winn of Lunenburg (wife Sarah, possibly Sarah Tench)
The key to the family relationship between Col. John and Col. Thomas is Thomas’s Lunenburg will.
Most importantly, Thomas named John Winn of Amelia (expressly described as “of Amelia”) an executor along with his wife Sarah, son William, and Lyddal Bacon. IMO, that is sufficient evidence standing alone that Col. Thomas and Col. John were siblings. The most loved, trusted, and capable members of the testator’s family were usually designated executors. Further, an out-of-county executor was not the norm, because he would necessarily have to travel to administer the estate. Col. Thomas surely named John of Amelia executor out of affection without any expectation that he would perform estate administration duties.
The witnesses to Col. Thomas’s will, who are traditionally also close family members, provide additional evidence that he and Col. John were siblings. Here are the people who witnessed Col. Thomas’s will:
… Members of the Amelia County Irby family, including Susannah Irby, Charles Irby, and Lucy Irby. Susannah was Susannah Winn Irby, proved sister of Col. John. Charles and Lucy Irby were Susannah’s children. Keep in mind that the Irbys had to make a trip across the Nottoway to witness Col. Thomas’s will. One had to witness the will when and where the testator executed it.
… the Winn witnesses were John Winn Jr. and John Winn. As you know if you follow this blog, Lunenburg was awash with Winns named John. That means my opinion is ripe for second-guessing. Because Col. John Winn of Amelia was named executor, I believe that he and his son John Jr. were witnesses.
I have saved the low-hanging (read: easy) fruit for last. Namely, whether Daniel Winn was also a sibling of Col. John, Col. Thomas, Susanna Winn Irby, and Phebe Winn Holland. I will refrain from reciting the many connections between Col. Thomas and Daniel in the Lunenburg deed records. Instead, I offer the following two items.
Naomi Giles Chadwick’s book, Winn – Daniel and His 9 Sons, states without any citation to county records that Col. Thomas testified in a deposition that Joseph Winn, son of Daniel, was his nephew. I haven’t found that deposition. If true, then Daniel Winn and Col. Thomas Winn were brothers.
There is one more will “factoid.” Joseph Winn and Elisha Winn, sons of Daniel Winn, witnessed Col. John Winn’s Amelia County will. All of the other witnesses (with the possible exception of Giles Nance) were Col. John’s close relatives. And, of course, Joseph and Elisha made the trip across the Nottoway to witness their Uncle John’s will.
With that, I’ll move on. More Winns are tugging at my sleeve.
See you on down the road.
 John Winn was commissioned a Lt. Col. in the Amelia County militia on 23 May 1771. Lloyd Bockstruck, Virginia’s Colonial Soldiers (Baltimore: Genealogical Publishing Co., 1988). My Air Force Academy graduate husband tells me that a Lieutenant Colonel is addressed as Colonel. I am doing that in this article.
 I am glossing over Phebe Winn’s maiden name in order to avoid a sidetrack into lengthy proof. I believe she was née Wilkes.
 Rosalie Edith Davis, Hanover County, Virginia Court Records 1733-1735: Deeds, Wills and Inventories (1979) 13-14, lease and release from Richard Winn and wife Phebe of Hanover to John Winn, 517 acres with a plantation on Chickahominy Swamp.
 Amelia Co., VA Deed Book 2: 82-83, lease and release from Stith Hardaway to Richard Winn of Hanover, 388 acres. The tract was then in Amelia but is now in Nottoway County, about 6 miles north of Effing Creek/Falls Creek/Hounds Creek where the Lunenburg Winns lived.
 FHL Film #1,902,616 has Amelia County tax lists including those for 1746, 1748, 1749, and 1751. Two of the tax lists identify his property as “Richard Winn list” or “Richard Wyn’s Quarter,” which means the taxpayer didn’t reside in the county.
 Amelia Co., VA Deed Book 15: 6, deed dated 24 Sep 1778 from John Winn of Amelia to his son Richard of same, for love and affection, 400 acres on the south side of John Winn’s mill pond, part of the tract belonging to the late Col. Irby adjacent John Winn and Charles Irby.
 Virgil D. White, Genealogical Abstracts of Revolutionary War Pension Files Vol. 4 (Waynesboro, TN: National Historical Publishing Co., 1992). Revolutionary War pension application No. W.6558 by Jane Pincham Winn, widow of Richard Winn, Virginia Line. View it here.. If it is correct that Col. John Winn was born in Hanover rather than a predecessor county, then he was born during or after 1721. Hanover was established in 1721 from part of New Kent County.
 My notes indicate that, years ago, Ann Avery Hunter somewhere (!?!) cited the accession number at the Virginia Archives for the marriage bond of John Winn and Susanna Irby, daughter of Charles Irby Sr. The bond was dated 4 Apr 1754. I cannot locate the accession number, nor can I recall where I found the reference. I nevertheless trust Ms. Hunter and my woefully incomplete notes on this fact.
 For Col. John’s birth date, see Note 7 saying that he was born in Hanover County. I estimated he was born after 1721 when Hanover was created but during the 1720s because he married in 1754, see Note 8. Colonial men (in my observation) typically married about age 25. His will was proved in January 1781, probably very soon after he died as was the norm. See Note 14.
 Amelia Co., VA Will Book 2X: 45, will of John Irby dated and proved in 1763. Executors wife Susannah Irby, “her brother John Winn,” and brother Charles Irby. Children Charles Irby, Lucey Irby, and John Irby. See also Kathleen Booth Williams, Marriages of Amelia County, Virginia 1735-1815 (Baltimore: Genealogical Publishing Co., Inc., 1978, originally published Alexandria, VA, 1961), John Irby and Susanna Wynne married 29 Jan 1757, surety John Wynn.
 Amelia Co., VA Deed Book 8: 314, deposition of John Nance re Michael Holland’s gift of enslaved people to his children Mary and Joseph. Nance testified that Michael Holland’s wife (unnamed) wanted the gift recorded and asked Nance to have her “brother Winn” take care of it. Nance’s testimony proves only that Mrs. Holland was née Winn. However, Susannah Irby, a proved sister of Col. John, also testified on the gift issue. Id. at 315. Finally, Mrs. Holland’s given name was Phebe. Amelia Deed Book 14: 1774 deed from Pheby Holland, widow of Michael Holland, and his son Joseph and wife Mary to Medkip Tomson of Amelia. That combination of facts convinced me that Phebe Holland was Col. John’s sister.
 Lunenburg Will Book 3: 75, FamilySearch.org film #32,380, will of Thomas Winn dated 18 Sep 1779, proved 12 Apr 1781. Thomas named six of his eleven children in his will, see the article about a chancery suit identifying all of his children.
 See Note 10.
 Col. John Winn had sons Richard, John, and Charles, and a daughter Jane Winn Epes. Amelia Co., VA Will Book 2: 360, will of Col. John Winn dated Mar 1780, proved Jan 1781. He named his wife Susanna (née Irby, daughter of Charles Irby Sr. and wife Susanna), sons Richard, John, and Charles, and daughter Jane Winn Epes. Executors were his wife, Truman Epes, and Charles Winn. Truman Epes was John’s son-in-law. Witnesses were Giles Nance, John Irby, William Gooch, Elisha Winn, Joseph Winn, and Jane Epes. I have long suspected that John Nance or Giles Nance married a Winn, but cannot prove it. John Irby’s wife was Susanna Winn Irby, sister of Col. John. William Gooch married Henrietta Maria Irby in Nov. 1769; Charles Irby testified that Henrietta was 21 and the daughter of Charles Irby Sr. Kathleen Booth Williams, Marriages of Amelia County, Virginia 1735-1815 (Baltimore: Genealogical Publishing Co., Inc., 1978, originally published Alexandria, VA, 1961).