Donald Sasser has made major contributions to the information and documents on Simeon Wilson.

There is no definitive proof of who Simeon's parents are. There is substantial evidence on the identity of his father.
Start with who his parents are not: Many online pedigrees list Richard Wilson and Mary Rutha Green. This is not possible on the face of it. Simeon consistently gives his birth year as 1800 in NC. Mary Rutha would have been 10 years old when he was born and it was 6 years before she and Richard were married. Many other online pedigrees list Jonathan Wilson and Sarah Cobb or Boone, found in early Clay and Owsley. There is no glaring reason why they cannot be Simeon's parents, but there is no reason to believe they are. Some also give Jonathan's father, Phillip, as Simeon's father. Still other list Jonathan and Mary Rutha Green. Mary Rutha did not marry Jonathan, she married Richard Wilson, as proven by a surviving 1806 Knox County marriage record. The late James Bowman did extensive deep research at the NC archives and elsewhere on the Phillip Wilson family and he does not include Simeon as a member of that family.
There is compelling circumstantial and secondary evidence to indicate Simeon's father was the John Wilson found in Knox and Harlan counties from 1811 until his death in 1834. Esther was the mother of his later children, but she would have been only 13 years of age when Simeon was born and it's unlikely she was his mother, leaving his mother completely unknown..Simeon's first appearance in public records is the 1820 Harlan census. where he is found in close proximity to John Wilson as well as Richard Wilson and John Williford. Richard Wilson's children are well documted, leaving John Wilson as his likely father.
Simeon's great grandson, Taylor Brown (son of Richard's daughter Mahalia) wrote a genealogy in 1928 as a class assignment at Lincoln Memorial University in Harrogate, TN. It is given high credibility due to the early date, his access to older Wilsons, and the fact that it has proven to be correct on all but a few minor points. He does not name Simeon's parents, but he lists his siblings. Among them are Easter Saylor (married John G Saylor) and Lucy Howard (m 'Cripple Ben' Howard). They along with Mary Ward are well documented in public records as daughters of John Wilson and Esther.
There is some DNA support for this belief, but all the probable children of John, with one exception, inter married with other southeast KY families and living descendants could match each other in multiple directions.

Individual Facts
Census 1820 Harlan County, KY page 120 line 297 Simeon is alone age 16-26

24 Aug 1821 (about age 21) 50 acres Puckett's Creek Harlan County, Kentucky; Harlan Co, KY

4 July 1829 Simeon bought 100 acres on Straight Creek from James and Rainy Napier for $150. The deed said it was a 100 acre survey originally in the name of William Green, and that Simeon already lived there.

1830 Harlan County Census
Simeon Wilson
1m less than 5 (Elijah b 1824?)
1m 20-30 (himself)
3f less than 5 (Catherine 1826, Sarah 1828, Nancy
1830?)
2f 5-10 (Clarinda 1820, Elizabeth 1819)
Nancy ?????????

1840 Clay County Census
Simeon Wilson
1m under 5 (Peter 1837)
1m 5-10 (Simeon Byrd 1832)
1m 15-20 (Elijah 1824)
1m 30-40 (himself)
2f under 5 (Angeletta 1839, Jensie 1834)
1f 5-10 (Nancy 1831)
2f 10-15 (Catherine 1826, Sarah 1828)
1f 40-50 (Nancy Willeford)
Clarinda age 19 and Elizabeth age 15 were married previous to the census and not listed

Census (10 August 1850): Simeon Wilson 50 farmer b. NC able to read and write Farmer
Nancy 53 b. NC unable to read and write
Sarah 22 b. KY unable to read or write
Nancy 19 b. KY
Simeon 18 b. KY
Jinsey 16 b. KY
Peter 13 b. KY
Augeteela 11 b. KY
Richard 9 b. KY
George 8 b. KY

Census (13 June 1860): 1860 Clay County Census
HH #347
Simon Wilson - age 59 - SC - farmer
Nancy - age 62 SC
Richard - age 19
George - age 17
John Jackson - age 7 (born Floyd Co)
George Jackson - age 5 ( born Clay Co)
Richard Sailor - age 19 - farm labor

Death (1865): At the time of Simeon's death, Leslie County, KY had not yet been formed. Simeon died in Clay County, KY but his burial site is in Leslie County.

Location of Wilson Cemetery: Across the road from the Beech Fork Church / Elementary School on Rt. 421 the road to Hyden in Leslie County - called Sim's Branch. Cemetery is set off the road on the right and is almost invisible from Rt. 421. The Church/School is on the left as your headed toward Hyden. There is a gravel road leading to the cemetery on the right. There is a small house on the right side of the gravel road and a field on the left. You can see the cemetery from Rt. 421, but you have to look carefully it's on the hill on the other side of the field. There is a set of wooden steps leading up to the cemetery.

For over a century the graves of Simeon Wilson and Nancy Williford Wilson were marked only by fieldstones. We know where they were buried because John L Wilson passed that knowledge on to his daughter Lillian. John L was around in Nancy's lifetime and probably witnessed her burial as a small child. (He also said that Simeon and Nancy's home was on the flat in front of the cemetery.) In 1996 a group led by Lillian Wilson and Rev Stanley Wilson replaced the fieldstones with a granite stone. That stone had some errors. In 2016 a different group replaced that stone with another one. This introduced different errors.
Errors on 1996 stone:
1. Simeon's death year is given incorrectly as 1870
2. Clarinda's death year is given incorrectly as 1892. Her tombstone gives the year as 1896 and that is consistent with probate records.
3. Peter's death year is given incorrectly as 1926
4. John is listed as a child. There is no evidence Simeon and Nancy had a son John. The John Jackson in their 1860 household is a grandson, child of Sally Wilson and Gabrtiel Jackson. The John Wilson mentioned in several estate documents is Angeletta's husband.
Errors on current (2016) stone:
1. There is a period following the I in Simeon's name implying that the I is the initial letter of his middle name. There is no evidence he had a middle name. The I on the earlier stone was meant to be a Roman numeral indicating that he was the first Simeon Wilson in the vicinity.
2. Clarinda's death year is still incorrect
3. Sarah's (Sally Jackson) death year is given incorrectly as 1843. She was party to a deed in 1890 and died after that. She is not found in any census 1900 or later.
4. Nancy's (Nancy Bailey) death year is given incorrectly as 1889. She is in the 1910 census and died after that.
5. Betsy (Chappel's) dates are incorrect. She lived a long life. Her tombstones gives the dates 9/8/1819 to 3/3/1894.

Simeon died in 1865. Richard Wilson, his son, executed a bond as administrator of his estate 6-5-1865, with Henry Brown as surety. This very likely means that Simeon died in the Spring of 1865, a couple of months previous. The inventory from his estate sale was entered in Clay County Court 9-16-1865.
We do not know precisely when Nancy died. She is living with son Richard at the 1870 census. She is a widow living with daughter Sally at the 1880 census (Leslie). A series of deeds transferring the property of Simeon Wilson appear starting 1884 in Harlan and Leslie County. It seems likely that the property remained in Nancy’s hands until her death.
The following are named in the settlement of Simeon’s estate 3-25-1869 Clay as receiving settlement for ‘a part interest in the estate’: Elizabeth Wilson, John Chapell, Henry M Lewis, Sarah Wilson. A.C. Turner, Nancy Bailey, S.B. Wilson, Levi Muncy, John Wilson and George Wilson. (Clarinda, Kate, Gincey and Angeletta’s husbands are mentioned, but not they. Sarah (unmarried) and Nancy (widowed) are mentioned by name. Betsey Chappell is named both ways). Peter is mentioned only as a debtor to the estate. R.L. (Richard) is mentioned only as administrator. Elijah is not mentioned. His last eight children are in his 1850 household. Betsy, Clarinda, Elijah, Kate are married and gone, but Elijah is very next house.

The correct list of children is::
Elizabeth Chappell (1819 - 1894)
Clarinda Lewis (1820 - 1896)
Elijah Wilson (1824 - 1899)
Catherine Turner (1826 - 1888)
Sarah (Sally) Jackson (circa 1828- after 1890)
Nancy Bailey (circa 1830 - after 1910)
Simeon B Wilson (1832 - 1905)
Gincy Muncy (1834 - 1916)
Peter Wilson (1837 - 1923)
Angeletta Wilson (circa 1839 - 1915)
Richard Wilson (1840 - 1923)
George Wilson (1842 - 1916)
These children are all named in an 1889 Leslie deed whereby Richard buys the interest of other heirs to property on Beech Fork and Laurel Fork
Sarah, Nancy and Angeletta's burial places are not known with certainty.
The dates for the others are from their tombstones.
Sarah and Nancy's death dates are not known.

Heirs of SIMEON WILSON©

Harlan County Deed Book L, page 505-506, is a deed between the heirs of Simeon WILSON and J B GROSS and others.
WILSON had given a title bond to Edmund GROSS and then died before he had executed a deed to the property. The heirs of Edmund GROSS brought suit to get the heirs of Simeon WILSON to convey the property.

Named as heirs in the deed, dated 8 Mar 1889, were:

Simeon B WILSON and wife Sally
Peter WILSON and wife Sarah
R L WILSON and wife Easter
George WILSON and wife Mary Jane
Elizabeth CHAPPELL, widow
Sally JACKSON, widow