Fourth Generation Inclusive

Historical Documents of Genealogical Interest to Researchers of North Carolina's Free People of Color

Tag: Wynn

They were sold for his debts.


A public sale of negroes took place in this town at the Court House steps on Saturday last, of which the following is an account.

Negro woman, aged 25 with two young children brought 883.

Negro girl, aged, 16, brought $711

Negro girl, aged 22,   “             808

Negro boy, aged 22, “              817

The first three were purchased by Dr. Dortch of Stantonsburg, the fourth by Mr. John Davis, of Lenoir and the fifth by Mr. Fourney Jernigan of Wayne. They were the children of a free negro by the name of Adam Wynne, who had purchased their mother, his wife, previous to their birth. – They were consequently his slaves and he having become involved, they were sold for his debts. – Goldsboro Tel.

The North-Carolina State (Raleigh), 17 March 1852.

[Sidenote: These four were not the first or last of Adam Wynn’s children to be sold to pay off his debts. — LYH]

He was in for the right thing.

Charles Wynn filed claim #9340 with the Southern Claims Commission. On 1 July 1872, he testified: “I am fifty-five years of age, reside in Wayne County, North Carolina …. I resided during the war in Wayne County, North Carolina, on my own land. It contained about 230 acres, 100 of which was under cultivation.” Tony Roberts, age 40, colored, testified that he lived about a quarter of a mile from Wynn during the war and saw him often. Roberts said Wynn “believed the Union army would succeed, that he thought its cause wasa right, and he was in for the right thing. He said that secession would ruin the country, and he thought its cause was right, and he was in for the right thing.” William H. Thompson, age 28, colored, swore that he had known Wynn for 24 years and saw him every four months or so during the war. He said Wynn “hoped that the Union army would be successful, put down the rebellion and do away with slavery” and revealed that the Confederate government occasionally pressed Wynn’s wagons and drivers into service to haul its goods. (Confederate archives revealed two vouchers for hauling arms from Fayetteville to Raleigh, dated in 1862, and signed by others on behalf of Wynn.)

In December 1898, a special attorney rejected the claims of Wynn’s estate: “We do not care to review the testimony in the case. If the testimony were offered in behalf of a white man under the same circumstances, it would scarcely be sufficient to prove loyalty. But in view of the fact that the claimant was a colored man, his loyalty must be largely presumed from his natural sympathies with those of his own color and those who were fighting, as the colored man believed, in his behalf.”

We cannot come to terms.

State of North Carolina, Wayne County   } Court of Pleas and quarter Session November term 1837

To the worshipful the justices of said Court — The petition of the Wilmington & Raleigh railroad company humbly complaining sheweth unto your worships that the road which they are now constructing will pass through the lands of Adam Wynn of this county, They represent unto your worships that they have not been able to come to any understanding or make any agreement with the owner Adam Wynn as to the terms upon which they may construct their road over his lands They therefore pray that thus court will cause the Sheriff to summon a jury of twelve lawful men to go upon the rout that may be pointed out by the President and Directors or by their agent and say what damage the owner will sustain by the construction of the road allowing or condemning sixty five feet on each side of the base. The jury also taking into consideration the value of the benefit resulting and that may result to the owner from the construction of the road and that the jury make a return to court under hand and seal of their proceedings they first having been duly sworn and your petitioners pray that this court will take all and such other steps touching the premises as may seem necessary and your petitioner as in duty bound will ever pray    /s/ W.B. Wright Sol. Pro Pet

Railroad Records, Wayne County Records, North Carolina State Archives.

Twelve acres lying east of the cross fence.

State of N. Carolina, Wayne County, March 31st 1884.

Know all men by these presents that I Itey Simmons being of sound mind and frail in body, knowing the uncertainty of life, and the certainty of Death and desiring to arrange my worldly affairs while I live – do make this my last will and testament  —

Item I. I commit my soul to God and my body to the Grave. I desire to be decently and plainly buried, and the expenses of my burial to be paid first out of any money I may have or the first that may be raised out of the proceeds of my property.

Item II. I give to my Grand-daughter Sarah Simmons, my cow and yearling.

Item III. I give in fee simple to my daughter in law Sally Winn widow of my deceased son David Simmons: Twelve acres of land, lying East of the cross fence between my house and hers, and next around and including the house where she is living, to be surveyed and marked only by competent Surveyor, under supervision of my Ex’r or Admin.

Item IV. I order all other property which I may possess of whatever nature Real and Personal, not otherwise provided for in this Will to be sold and converted into money, as promptly as the best interest of my Estate will allow or require: and then: my burial expences above refered to, and any just and legal debts I owe, being paid, I order –

Item V. That the sum of one hundred Dollars shall be appropriated out of the proceeds of my Estate, and given my Great Grand Child Julia Jordan. My executor is requested to see that this money is safely invested, and the interest or profit from the same used for her benefit. The principal to be reserved until her majority; unless absolutely required for her necessities or her best interest before hand –

Item VI. The balance of money now remaining after above I bequest I order to be divided into three equal parts – and to be given one part to my Grand Daughter Maria Thompson one part to my Grand daughters Sarah Simmons and Gustus Greenfield equally and the other part to my son Moses Simmons, if he living, is [sic] he is dead, and leaves no legal heirs of his body, Then this part bequeathed to Moses Simmons shall be divided one half to Maria Thompson and balance between Sarah Simmons and Gustus Greenfield, my Grand-daughters above mentioned.

Item VII. I assign David W. Kelly my Executor to this my last will and Testament as witness to all of which I hereunto set my hand and seal. This day and date as above written, Itey X Simmons {seal]

Signed and sealed In presence of J.F. Oliver, S.J. Kelly

Wayne County Will Book 1, Page 255, Wills, North Carolina State Archives.

The Winn family.


Winn Family Marker, Center Street, Mount Olive.

Photograph by Lisa Y. Henderson, March 2013.

[Sidenote: And thus, myth is codified.

There’s no question that the early 19th century Winns were a remarkable family.  However, to my knowledge, there is no definite evidence that there was an Adam Winn Sr., father of Adam Jr., Charles, Gray, Levi, and Washington Winn.  There were at least two Adams, as deduced from the dates of deeds. Though it’s not clear when the first one lived, the second was born circa 1805.  (What does the 1790 date relate to?) My research suggests that Charles Winn in fact was the son of Charles and Jinny Winn and had a brother named William Winn. The records also reveal a James Winn who bought and sold property with his kin. There are, moreover, contemporaneous female Winns, whose relationship to the “five brothers” is unaccounted for.

There is no definite evidence that Adam Winn (the one known as “Jr.”) ever married, but he had three or more sets of children. The oldest (Charles, James, Woodard, Marshall and Woodley) were born slaves to one or more enslaved mothers (one named Venus). Two other sets, the Newells and Parkers, who primarily used their mothers’ surnames, were born to white women. — LYH]

W. Frank & Sarah Simmons.

ImageWILLIAM FRANK SIMMONS was the son of Bryant Simmons and Elizabeth Wynn Simmons.  SARAH WYNN SIMMONS was likely related to Frank’s mother, but her parentage is not clear. They are buried at First Congregational Church cemetery, Dudley, Wayne County.

Two tracts on Mumford Street.

Washington Winn to Lewis W. Levy.

This Indenture made this 15th day of November in the year of our Lord One Thousand eight hundred and Fifty three between Washington Winn of the County of Wayne in the State of North Carolina of the one part and Lewis W. Levy of the County of Cumberland and State abovesaid of the other part. Witnesseth, that the said Washington Wynn for and in consideration of the sum of twelve hundred Dollars to him in hand paid by the said Lewis W. Levy at and before the sealing and delivering of these presents the receipt whereof he doth hereby acknowledge hath given, granted and bargained, Sold, aliened, remised, released, and confirmed, and doth by these presents, give, grant, bargain and sell, alien, remise, release, and confirm unto the said Lewis W. Levy his heirs & assigns all that tract or parcel of land, situate lying and being in the Town of Fayetteville in the South Side of Mumford Street and Beginning at the North East corner in the margin of Said Street and runs as the said Street about South 70 East to within three feet of Sampsons North West corner in said Street. Thence parallel with said line of Sampsons Lot to within three feet of Sampsons back on South West corner. Thence to a stake within about eight feet of the said Phillis Dennis South East corner of her back lot.  Thence to her corner, thence with her line to the beginning corner on the margin of Mumford Street. It being a lot of land Sold by Thomas J. Curtis to Phillis Dennis 13th Novr 1840 & registered in Book V, No. 2, page 475. Also one other tract of land Beginning at the intersection of Mumford and Robinson Streets on the South side of Mumford Street and runs thence South [illegible] East one chain and (50) fifty two links. Then South [illegible] West two chains & Sixty links to the corner of Lot No. 5. Thence North Seven and half degrees West one chain eighty four links to Robinson Street. Thence at Robinsons Street two chains to the Beginning. Being Lot No. 1 conveyed by Isaac Newberry to Phillis Dennis & Registered in Book K [illegible] 2, page 199. To Have and to Hold the said Land with its appurtenances to the proper use, behoof and benefit of the said Lewis W. Levy his heirs and assigns forever. And the said Washington Wynn for himself and his Heirs, Executors and Administrators doth covenant, promise and agree to and with the said Lewis W. Levy his heirs and assigns, that he the said Lewis W. Levy his heirs and assigns and every of them, shall have hold, occupy, possess and enjoy the said Land, with its appurtenances, without any let, suit, hindrance, molestation or eviction from or by the lawful claim or claims of any person or persons whatsoever, to warrant and forever defend. In testimony Whereof, the said Washington Wynn hath hereunto Set his hand affixed his seal, the day and year first above written.  Washington Winn

Sealed and Delivered in Presence of James Banks

State of North Carolina, Cumberland County  } April 18th 1854

Then was this Deed proved before me John McLaurin

Grantee Book 51, p. 542, Register of Deeds Office, Cumberland County Courthouse, Fayettevllle.

Pinkney Wynn.

ImagePINKNEY WYNN was born about 1840 to Levi and Bertha Winn, probably in northern Duplin County. He married Elizabeth Winn, who was probably his cousin, but whose parentage is not clear. He is buried in First Congregational Church in Dudley, Wayne County.

Photo by Lisa Y. Henderson, March 2013.

Charles & Frances Wynn.

ImageCHARLES WYNN was born about 1842, probably in northern Duplin or southern Wayne County, to Levi Wynn and his wife, Bertha. FRANCES ALDRIDGE WYNN, probably born in southern Wayne County, was the daughter of John Matthew Aldridge and Catherine Boseman (or Simmons) Aldridge. They are buried in the cemetery of First Congregational Church, Dudley, Wayne County.

Photo taken by Lisa Y. Henderson, March 2013.

44 acres on Calf Pasture branch.

Know all men by these presents that we Lovett Reaves & Milly Reaves of the State of Georgia & County of Hancock Know ye that we Lovett Reaves & Milly Reaves for & in consideration of the sum of One hundred and ten dollars to us in hand paid by Jane Winn of the State of North Carolina & County of Duplin before this executing and delivering of these presents, the receipt whereof we hereby acknowledge & confess that we are therewith fully satisfied contended and paid & for these same considerations have given granted sold & assigned & set [illegible] to the said Jane Wynn her heirs and assigns forever a certain tract or parcel of land [illegible] lying & being in the County of Duplin & State of North Carolina on or near the head of the Calf Pasture branch, it being part of a tract of land belonging to the late Reuben Johnston &c and it also being the part of land that fell to the said Milly Reaves in the division of the said land by heirship, beginning at a stake in the old line & runs north with the old line N 45 poles to a stake Felix Johnson’s corner, then with his line W 158 poles to a stake his corner over the road then S 45 poles along the old line to a stake then W 158 poles to the first station including the house & field on the Road containing Forty four acres more or less together with all do privileges rights [illegible] and appurtenances to the said parcel of land & premises of the same to the use benefit & behoof of the said Jane Wynn her heirs & assigns to have & to hold forever & the said Lovett & Milly Reaves doth for themselves their [illegible] said parcel of land forever & the said said Jane Wynn shall & will warrant & forever defend from themselves their heirs executors adm’r & assigns & all other persons whatsoever. In witness whereof we the said Lovell and said Reaves [sic] hereunto set our hands and seals this twenty second day of February in the year of Our Lord Eighteen hundred & eighteen.   Lovett Reaves    Molly X Reaves

Signed sealed & del’d in the presence of Asher Flowers, Thomas X Gray

State of No Carolina, Duplin County. October Term 1818. The within deed was proved [illegible] by the oath of Asher Flowers & order to be registered. Test Wm. Dickson C.C.

Grantor Book DTFU, page 415. Register of Deeds Office, Duplin County Courthouse.

[Sidenote: Jane (or Jinny) Winn was a sister or mother or cousin of the male Winns, farmers and mechanics, who amassed property in the thousands of acres in Duplin, Wayne and Cumberland Counties. Much of it was lost in the decade before the Civil War. More later…. — LYH]