John Winn was a Virginian who took the path of a pioneer as he followed the frontier in the search for available land and moved his family first to Kentucky and then Ohio where he amassed substantial property. But he also had the foresight and moral courage to free the slaves he inherited when he chose to settle in a free state, and indeed, they were still on his mind when he wrote his will and ensured that their freedom would not be challenged by any of his heirs (see his will below). Some sources report his middle name was Joseph, but the documentation for this is not clear thus far.

John was the son of John Winn (d. 1781) and Susanna (Epps ?) Irby (d. 1795) who married in Amelia Co., Va. on 4 Apr. 1754. The source for this is "A Family History of the
Wynns (Winn, Wynne) of Virginia, South Carolina, and Georgia, and Other Related Line" by Charles Arthur Wynn, Jr. and Louise Tompkins Wynn (Anusden Publishing Co., 1991).

In support of this is the fact that John gave his mother's family name Irby as the middle name of his son Douglas and daughter Martha, and possibly his daughter Myrtilla. Also, John received 30 pounds specis on 17th September 1791 from Charles Winn as his full share of the estate of his father John.

Married twice:

1st marriage - 14 Dec 1787 in Lunenburg Co. Va., Myrtilla Minor (b. ca. 1764 Virginia, d. 1 Aug. 1822 Champaign, Ohio); she is reportedly the daughter of Joseph Minor and Edith Cox of Lunenburg Co.;

2nd second - 26 May 1823 in Ohio to Margaret (Rector) Turman who was the widow of Isaac Turman .

Children of first marriage:
- John, Jr. (b. ca. 1794; married three times; 1st to Mary Powell in Champaign Co. Ohio on 23 April 1822 and she died before Feb. 1832; 2nd to Mary Turman on 17 Feb 1835 - she was born 7 Apr 1815, and they divorced in Illinois 1838; 3rd to Elizabeth Seeley on 19 May 1838 in Sangamon Co. Ill. where his brother Charles lived - they are together on the same page of the census);

- Martha Irby (b. ca. 1790, Va.; d. 19 Dec. 1848, age 58, married of William McRoberts, d. 17 Oct. 1860, aged 71 years);

- Richard (b. Abt. 1791, Va,., d. bef. Dec 1823, Clark Co., Ohio; m. Rhoda Turman on 5 Jul 1823, Clark Co., Ohio; b. 14 Feb 1806, Springfield, Clark Co., OH; d. Dec 1823, Ohio);

- Susana I. (b. ca. 1790, d. 28 Sept. 1823, age 31, wife of Aquilla Bishop);

- Douglas Irby (married Elizabeth Rawlings, and settled in Callaway county, Missouri in 1836.; children Mary, Myrtella, John, Elizabeth,Thomas, Richard, Melvina, Douglass, Jr., Martha, William, Susannah and Ascenia according to the "History of the Pioneer Families of Missouri with Numerous Sketches, Anecdotes, Adventurs, Etc., Relating to Early Days in Missouri" by Bryan and Rose - 1876);

- Jane (married John C. Caldwell);

- Dr. Charles L. Winn (b. 1800, d. August 17, 1847 - see link below);

- Myrtilla (b ca. 1800, d.. 29 September 1840, age 40; her father's will states she was "afflicted;" one researcher, Charlotte Holder, reports that another relative, Mary Connolly stated it was from a fall from a horse).

Child of 2nd marriage:
- Hosea Ballou Winn.

Perhaps the earliest written record of John Winn is as part of a land transaction reported in Lunenburg County, Va. on 15 June 1787 ("Virginia, Deed Book 15," page 168). This was a transfer of 172 acres for 200 pounds by Cyrus Minor to Bartlett Minor, the brothers of his wife Myrtilla. The deal must have been part of the distribution of the estate of their father Joseph Minor. Both John and Myrtilla signed as witnesses.

A brief biography of John Winn is included within the biography of his grandson James G. Caldwell in "The History of Champaign County, Ohio"(W. H. Beers and company, 1881):

"John Winn, the grandfather of M. Caldwell, entered the land known as 'Pretty Prairie," in 1805, and James still owns the original tract, that to this day never had a mortgage or other incumbrance on it. John Winn was a Virginian by birth, came to Fleming Co., Ky., in 1796. He came to Kentucky from Virginia in an ox-cart, with no property save one negro boy and his cattle. He was well educated, and commenced teaching a school in the neighborhood. Mrs. Winn's name was Minor, and she had inherited twenty negroes from her father's estate. John freed all the negroes when he left Kentucky, and gave his name as security for their good behavior. They had seven children - Jane, Susan, Douglas, Richard Martilla and John. He was converted under the ministrations of Rev. John Smith, of the Baptist Church. When the meeting was over, Brother Smith announced that Brother Winn would be baptized next Sabbath, and that he hoped there would be good attendance. 'God bless you, Brother Smith,' said John, 'life is too uncertain to wait, and I want to be batized at once.' It was accordingly attended to by candlelight. Adter the conversion of John, he came to the conclusion that all the world was to be saved, and embraced the Universalist faith. Saying that God had done much for him, and he would do something for God at his own expense, he erected the church at Springfield. This will ever be a monument to his memory" (637-8).

Some of the story about John is repeated in a later text, but it does add other details. The information is part of the biography of Thomas Rawlings reported in "A Centennial History of Champaign County, Ohio" (1902):

"James Rawlings, father of our subject, married Susannah Irby McRoberts, in 1829. She was born September 16, 1810, while her parents were on their way from Kentucky to Ohio. Her father, William McRoberts, was born in Kentucky, his father having been a native of Ireland, whence he emigrated to America and became a pioneer of Kentucky. William McRoberts married Martha Irby Winn, daughter of John and Myrtilla Winn. John Winn was born December 31, 1759,
in Virginia, and came to Fleming county, Kentucky, in 1796, in an ox-cart with one negro boy and his cattle. He was well educated and taught in the neighborhood. When he left Kentucky he freed his negroes and became responsible for their good behavior. Removing to Ohio, he entered land on Pretty Prairie in Champaign county, some of which is still held by his descendants. He died at his home in
Springfield, Ohio, September 11, 1838. He was married to Myrtilla Minor on Friday, December 14. 1787 by Rev. Thomas Grimes. She died August 1, 1822. Martha Irby Winn was horn July 11, 1790 and died December 19, 1848."

The name of the minister that married John and Myrtilla has an alternate spelling as reported in "Marriages of Lunenburg County Virginia 1746-1853," compiled and
published by Emma R. Matheny and Helen K. Yates. The text shows that John Winn married Myrtila Minor on 14 Dec. 1787 by Thomas Crymes (137).

Researchers identify several stages of John's move west:

1. From Va. (from Amelia, Nottoway or Lunenburg counties) to Mason County, Ky. by 1798. It seems at this time John disposed of property in Virginia as indicated by a deed from John Winn, of Mason County, Ky., and John Tabb, of Amelia County, Va., to Freeman Epes, of Amelia, to land on Lazaretta Creek, adjoining lands of Peter Randolph and Robert Fitzgerald. Freeman Epes was John's brother-in-law married to Jane Winn. In fact, there was an earlier deed from John's relative Richard Winn to Freeman Epes in 1788 for land offered in exchange for a loan from Epes.

2. From ca. 1800 to 1812 Fleming County, Ky.; the 1800 Tax List of Fleming Co., Ky, names John Winn, dated Aug 11, 1800. John "Wim" is listed in the 1810 Kentucky Census, Fleming Co. (Image 1, page 61); 2 boys under 10, (Richard and Charles), 1 young teen boy 10 to16 (John Jr), 1 young man 16 to 26 (Douglas Irby), 1 man over 45 (John Winn Sr.), 1 girl under 10 (Myrtilla), 1 young teen girl 10 to 16 (Jane), 2 young women 16 to 26 (Martha and Susannah), 1 woman over 45 (Myrtilla Sr.). John seems to have acted as the attorney: "From Mason County, Kentucky Deed Book A-L, 1789-1810" on page 192: "Thomas Hart, Merchant, of town of Lexington, Ky appts John Winn of Mason co his attny to convey lands conveyed to him by Littleberry Mosberry, heir at law to John Mosby, dec'd; land lying in Fleming Co.. Fayette co clerk: C. Beatty Clerk: Thomas Marshall, Jr.
Court records indicate he was in Fleming Co. on 30 April 1808, and acting as a witness on 16 May 1811."

3. From ca. 1812 to 1823 Champaign County, Oh. In Fleming Co. court records John Winn is identified as living in Champaign, Ohio on 19 Oct. 1813. He had amassed the funds to buy an entire section of 680 acres in Section 18, Town 5, Range 10. This was in the heart of the area called "Pretty Prairie" which was blessed with a level surface, natural drainage, and great fertility. But this was not his only property as the will and other documents attest.

4. From 1823 to 1837 Clark County, Ohio. The 1830 US Census for Ohio, Clark County, German Twp., includes children of both John's and Margaret's previous marriages: 3 boys in 5 to 10 range (including Hosea Ballou Winn); 1 young man 15 to 20; 1 man 20 to 30; 1 elderly man 70 to 80; 1 girl 5 to 10; 1 young teen girl 10 to 15; 1 young woman 15 to 20; 1 woman 40-50.

Family connections between the Rawling and Winn families suggests they emigrated together from Virginia to Kentucky and then on to Ohio. Persley Rawlings was a generation older than John, but his son Thomas Rawling was a contemporary. Their children intermarried as Douglas Irby Winn wed Elizabeth Rawlings, and her brother James Rawlings married John's granddaughter. James named his oldest son William John Winn Rawlings, and his youngest son Douglass Winn Rawlings.

This family connection is discussed in "A Lineage and Brief History of the Rawlings Family - Complied by a Descendant," released by W. J. Knight, Urbana, Ohio (March 1 1931):

" . .. . John Winn whose coming to this county from Fleming County, Kentucky influenced six of the sons and daughters of Thomas Rawlings to come, visit, William, James, Elizabeth, Barbara, Malinda and Sally."

"John Winn deserves a place in this memorial of our ancestors. I never knew him, as he was one of the pioneer settlers in Champaign County, Ohio, entering land here as early as 1805. James Rawlings married his granddaughter, and his sister, Elizabeth, married his son Douglass Irby
Winn.

"I have often heard James Rawlings speak of John Winn. He gave me the impression that John Winn was a remarkable man. I have heard him tell many times a story that illustrated John Winn's adeptness with figures. The story was that he could count a flock of geese flying over his head at the same time he was counting a drove of hogs coming through a gate. The rapid use of figures was handed down to succeeding members to the Rawlings family, some of whom could calculate easily and rapidly."

John's Will

In the name of God Amen. I John Winn of Clark County, town of Springfield of State of Ohio being now in The seventy ninth year of my age, & believing that ere long I shall come to remain in my present state of existence & being of a sound mind & memory do therefore make & ordain this my last Will & Testament in manner & form following-

And first it is my will & desire that all my just debts be paid & in case any person should suffer any loss whatever in consequence of having endorsed for me that my Executor pay to the person or persons suffering all the loss of damages they may have sustained out of my Estate.

Item. I give & bequeath to my beloved wife Margaret (?) Five hundred dollars, I also give her in trust for my son Hosea Ballou Winn until he arrives to lawful age, provided she remains my Widow, Three hundred & ninety one acres & fifty two poles of land lying on the east side of Mad River & is a part of Section 4 & 10 in Township 4 & Range 10, on Miami River, one half of the rents or profits of which farm I give to my beloved wife while she remains my widow, the right profits or rents of the other half I give to my son Hosea Ballou Winn. I also give in trust to my beloved wife provided she remains my widow for my son Hosea Ballou Winn until he comes to lawful age, the following property (to wit) four of the best horses & four of the best cattle I may die possessed of, the best wagon & (?), my carriage and harness, all my farming utensils, my Brap(?) clock, my silver plate, the whole of my household of kitchen furniture, including my secretary, bookcase of books, desk, beer cans, sugar chest, beds of furniture & bedsteads &
every kind of furniture whatever & the stove A& pipe now in use in my kitchen & all my sugar kettles & when my son Hosea Ballou Winn comes to lawful age, it is my will & desire that the land & personal property left in trust with his mother for him provided she still remains my widow should be equally divided between my beloved wife Margaret Winn & my son Hosea Ballou Winn, the half taken by my beloved wife I give to her during her widowhood, the other half I give & bequeath to my son Hosea Ballou Winn& his heirs forever. I also give and bequeath to my son Hosea Ballou Winn the land & personal Estate given to my wife during her widowhood. It is my desire that he takes possession of the same at the aspiration of his mother's widowhood & to him & his heirs forever. I give & bequeath the same, it is also my will & desire that my family be supported until the present crop is gathered & the provisions of meat grain & that is now have on hand. It is also my will & desire that should it be the will of my heavenly father to call me home before I receive the rent from John Gregory & Samuel Graybill that she be entitled to said rent one half I five to her for her benefit & the other half to my son Hosea Ballou Winn, It is also my will & desire that my beloved wife act as guardian for my son Hosea Ballou Winn & that she have
the privilege to part with any livestock or rent in her hand provided she may think that it may be for her interest & the interest of my son Hosea Ballou Winn & that she have my said son Hosea Ballou Winn well educated & that as to his education she would be governed by the advice of my son Douglas I. Winn who promised me he would attend to his education.

Item. I leave in trust with my executor for my afflicted daughter Myrtilla Winn one thousand five hundred dollars to be appointed by my executor for her special benefit & support in the most economical Manner during her life, & in case my said daughter should die leaving a child or children that she or they shall be entitled to the balance of said sum put in trust as before described by he she or them to be perpetuated forever.

Item. Whereas I was one of three persons appointed as a committee to attend to the building of a house of worship in The town of Springfield in which there will be free privilege to preach the glorious gospel of our blessed Redeemer & whereas I promised to be at the expense of one thousand dollars toward building & finishing said house seven hundred & fifty five dollars 81
1/2 cents I have paid & am bound to pay builder orders given in my name and included in The sum mentioned & no one of two of aforesaid committee I am involved perhaps for one thousand dollars more, it is my desire that my executor settle up & pay the balance that my be behind of the thousand dollars & if I am compelled to pay more than the thousand dollars & the friends are unwilling to refund the over plus to my heirs that he request the church to sell the basement story & part of the loft & refund the over plus to my estate or heirs as i truly contribute $1000, but more in my view would be wronging some of my legatees

"Item. I give to my son Douglas I. Winn two hundred dollars, on account of his affliction and large family

"Item. I also give to my two sons, John Winn & Charles Winn & my two daughters Martha I. McRoberts & Jane Caldwell five dollars each & also five dollars to be divided among the children of my Dau. daughter Susanna I. Bishop.

"Item. It is my will & desire that my executor sell at private or public sale as he may think best all the personal property that I may die possessed of not given away, also the tract of land I purchased Of William Eby containing 194 57/100, also the 70 acres deeded to me by the Albins, also the tract I purchased of Bakers heirs containing about 96 1/2 acres & also my lotts in The town of Springfield purchased of Jake Christie & James Christie & also collect all debts due me by bond or otherwise & after paying all my debts & legacies & my executor what the law allows him for his services & my funeral expenses, it is my will & desire that the balance that my be remaining should be divided among my first children (to wit) Douglas I. Winn, Martha McRoberts. the children of Susannah I. Bishop dec. to draw one child's part, Jane Caldwell, John Winn, Charles Winn & Myrtilla Winn, that is provided no attempt is brought by them against my estate in consequence of a legacy left them by my mother which legacy has been discharged by me in giving & paying my children each of them more than twenty times the amount of their part of said legacy & provided they bring no other accompt against my estate, nor attempt to bring into bondage those colored people that I emancipated in Kentucky & should either of them bring any accompt against my estate, or attempt to bring those poor unfortunate colored people into bondage, it is my will & desire that they should draw no part of my estate, nor any part of the estate left to my son Hosea Ballou Winn should he die before he comes to lawful age, but incase there is no accompt brought against my estate & no attempt made to enslave the colored people aforesaid, it is my will & desire that the balance of my estate after paying my debts & legacies etc. should be divided in the following manner. To my son Douglas I. Winn I give one fourth part of the remainder to be equally divided among such of my children as may bring no accompt against my estate & make no attempt to bring into bondage the colored people above mentioned, my dec. daughters children to draw a child's part & in case my son Hosea Ballou Winn dies before he comes to lawful age, it is my will & desire that my beloved wife's children should draw one third of the estate bequeathed them & my children before mentioned that may bring no accompt against my estate nor attempt to bring into bondage the colored people aforesaid should draw two thirds of the estate bequeathed my son Hosea Ballou Winn, to be divided among them as I directed The balance of my estate should be divided, the third drawn by the heirs of Isaac Turman Dec. to be equally divided among his children that may be living when the legacy is drawn, and lastly it is my will & desire that my body may be plainly & decently buried & that something be set up at my grave showing where I lie, my age etc. I now appoint my son Douglas I. Winn my executor & if he is providently hindered so as to prevent him from attending to the business it is my desire that my son in law William McRoberts acts as my executor of this my last will & testament, hereby revoking all former wills by me made & confirming this alone to be my last will which I seal, publish & declare this first day of August in the year of our Lord one thousand eight hundred & thirty eight.
John Winn (seal);

Signed, sealed & acknowledged in the presence of: James L Christie, Jonathan Lehman, J. Christie, William R?; State of Ohio, Clark County

"As the last will and testament of John Winn being before the court forprobate Jepe Christie & Jonathan Lehman two of the (witnesses) being sworn depose and say that they were present at the execution of said will that they hence ? testate acknowledge the same to be his last will and
testament that they signed the same at his request and in his presence and in the presence of each other and that he was at the time in their opinion of sound and disposing mind and memory and under no restraint and further they say not.

"Sworn and subscribed in open court, the 5th day of October AD 1838: J. Lehman, J. Christie"

Two other documents for John occur after his death. One helps show the family's use of property, and the other concerns tidying land title to settle the estate.

"Filed 13 March 1840 Charles Winn vs Executors of John Winn. John Winn, late of Springfield, Clark County, died in September of 1838. After his second marriage in 1824, he deed land on 12 July 1826 to his son, Charles Winn of Fleming County, Kentucky for 215 acres of land located in the north—west and south—west quarters of Section 12 Township 5 Range 10 (Urbana Tp., known as Pretty Prairie) and 25 acres in the north—west quarter of Section 14 Township 5 Range 11 (Urbana Tpá.) When Charles needed money to be a physician he deeded the land to his brother, Douglas 3. Winn, who gave Charles $1500 for the land. The witnesses for Charles' deed in Fleming County, Kentucky were John Taylor and William Pearce. Benjamin Northcott and Truman Day were the JPs. The deed between Douglas and Charles was dated 24 Sept 1827 and recorded in Champaign county Deed Book H Number 1, page 43, by David Vance. On 14 April 1828 the father, John Winn, purchased the land from Douglas. When John Winn died he left the property to his son, Hosea Ballou Winn, a child of his second marriage. John had married Mrs Margaret Turman on 26 May 1823. At the time of the suit, Charles, a resident of Illinois, felt that Hosea B. Winn had received more than his share of the estate. The court ruled that $366.33 was due to Charles from John's estate" ("Record Book 16, " page 485).

"Filed 8 March 1841 John Winn Caldwell vs Douglas 3. Winn et al. John Winn deceased, late of Clark County, Ohio, on 11 August 1834 was seized of 82 acres of the east half of the south—west quarter of Section 6 Township 5 Range 10 (Urbana Tp.). John Winn entered into a contract with John C. Caldwell to sell the land. John C. Caldwell transferred the contract to John Winn Caldwell who has fully met the payments and needs a deed from the heirs. The heirs were: Douglas 3. Winn of Missouri; Charles Winn and John Winn Jr. of Illinois; Martha wife of William McRoberts; Jane wife of John C. Caldwell; Myrtilla Winn; Susannah deceased wife of Aquilla Bishop left heirs: Jane wife of Robert S. Reid, Myrtilla Bishop and James Bishop; Hosea Ballou Winn of Clark County and Margaret, widow of John Winn, of Clark County" ("Record Book 18," page 52).

One further document establishing family connections was created by John's "afflicted " daughter Myrtilla. Her grandfather John Winn had left a will in Amelia Co., Va., and Myrtilla sued her father's estate for her share of the estate of her grandmother Susannah Winn. The action was filed in Champaign Co., Ohio and includes the will of Susannah Winn of Nottoway Co.

As for Margaret and the younger children, the 1840 census shows the family still in German Township in Clark Co., Ohio. There were three young men 15 to 20, one young woman 15 to 20, and Margaret herself in the 50 to 60 column.

The grave of John's first wife Myrtilla Minor and some of his relatives was located in s small burial ground on the family farm as was often the tradition of the time. This was found on the east of line of Section 18 by the roadside. According to "Rawlings, A Lineage and Brief History of the Rawlings Family - Compiled by a Descendant" (1930) six graves could be identified:

- Myrtilla, wife of John Winn, Sr. died Aug. 1, 1822, aged 58 yrs.
- Chas. Winn died Aug. 17. 1847, aged 47 years.
- Myrtilla, daughter of J & M Winn died Sept. 2, 1840, aged 40 yrs (evidently Chas. and Myrtilla were twins)
- Martha (Irby Winn), wife of Wm. McRoberts died Dec. 19, 1848, aged 58 yrs.
- Susana I. (Irby Winn) wife of Aquilla Bishop, died Sept. 28, 1823, aged 31 yrs. (Martha and Susana were daughter of John Winn)
- William McRoberts died Oct. 17, 186-, aged 71 yrs.