As promised, here is the will of Samuel Woodruff who died in Spartanburg County, South Carolina in late 1835 or January 1836:

Will of Samuel Woodruff
Spartanburg County, SC WB C:85-87
Source: FamilySearch

South Carolina
Spartanburg Dist.
In the name of God Amen I Samuel Woodruff Ser of the State and District aforesaid, Being weak of body but of perfect mind and memory, Thanks be to God & Calling to mind the mortality of my body and knowing it is appointed for all men once to die, I make and ordain this my last Will & Testament. That is to say principally and first of all I give and recommend my Soul into the hands of Almighty God that gave it, and my body I recommend to the earth, to be buried in a decent Christian manner at the discretion of my Executors; nothing doubting but at the General resurrection I shall receive the Same again by the mighty power of God. And touching such worldly estate wherewith it hath pleased God to bless me with in this life, I give and dispose of the same in the following manner and form –

Item 1st I give and bequeath unto my beloved wife Nancy Woodruff all the tract of Land lying on the Enoree River whereon I now live, it being the same I bought of William Shackelford and bound as follows: Beginning at the mouth of the cool spring branch of said Branch to the head thence along a fence to a Post oak thence a strait Aim with Allen’s Land to a pine corner, Thence S.67W.7.60 to a stump; thnce N.15W.10.60 Red oak, thence S74.W.41 to the Enoree hickory corner, Thence with the river as it meanders to the beginning mouth of the before mentioned cool Spring branch –

Also my will is that I give my wife four nigroes, namely Patience, Lyd, George & Perry and all their increase from the date of this Will – my riding chair, my black walnut cupboard my walnut chest, my big Bible, one bed and furniture her choice, one bedstead (?)and the (old?) blue curtains, and my (wheat?) fan and the said bed, furniture bed stead cord & curtains and all my wearing apparel for my wife to dispose of as she pleases –

Item 2nd Now my will is that all the remainder of my property both real & personal that I may have at my decease, except what I have willed to my wife to be sold and my wife to have five hundred dollars, and the remainder to be disposed of in the following manner.

My daughter Hannah Pilgrim has received two hundred & eighty nine dollars. I will her eleven dollars more to make her three hundred dollars, my son Joseph Woodruff has received two hundred and ninety five dollars and I will him eighty dollars more to make him three hundred & seventy five dollars ; my son Moses Woodruff has reieved three hundred & fifty eight dollars; I will seventeen dollars more to make him three hundred & seventy five dollaars. My will is that the above named children; Viz Hannah, Phebe (sic – Phebe is not mentioned before this spot!), Joseph, and Moses shall have the sums above named to them and no more of my Estate. –The remainder of my Estate after the above legacies are paid out to be equally divided between my six following named children in proportion to what they have already received, as follows, my son Aaron Woodruff has received four hundred & forty dollars, my son Amos Woodruff has received four hundred and five dollars, my son Richard Woodruff has received four hundred dollars, my son Gidion Woodruff has received five hundred and fifty dollars, my daughter Rebecca Bobo has received four hundred and twelve dollars, my son Isaac Woodruff has received four hundred dollars.—

Item 3rd And also my will is that at my wife’s decease that all the property I leave her, both real and personal as her dower, with its increase to be sold and the proceeds to be equally divided between my following named children, that is to say, Aaron Woodruff, Amos Woodruff, Richard Woodruff, Gidion Woodruff, Rebecca Bobo & Isaac Woodruff. I likewise make & ordain my sons Amos & Richard Woodruff my Executors of this my last Will & Testament I do hereby ratify and confirm this and no other to be my last Will & Testament In testimony whereof I have hereunto Signed sealed and acknowledged the same in presence of all the Subscribing Witnesses 11th July in the year of our Lord one thousand eight hundred & thirty five—

Samuel Woodruff (Seal)
William Jones S.M
Wm Clayton
Ely Cox

South Carolina
Spartanburg Dist.
The foregoing will of Samuel Woodruff Decd. was duly proven in Solemn form by the Evidence of William Jones William Clayton & Ely Cox the Subscribing Witnesses and ordered to be admited of Record.
24th Jany 1836 Jno. Bomar OTD

Having taken early Woodruff research at face value and not having done any real research of my own, I lately decided it was time to take another look at this very tangled family.

The immigrant generations are fairly straight forward, having settled in New York and then Westfield, Union, New Jersey. The problems were created when (1) they all started naming their children with the same given names and (2) the families migrated, mob-style, to the southern colonies before the Revolutionary War.

I am trying to prove family connections with actual documentation, which isn’t provided in the century-old research published on this family.

Today’s problem is proving that the father of Joseph Woodruff who died in Hopkins County, Kentucky was the son of Samuel Woodruff who married (1) a cousin, Jennet Woodruff and (2) Nancy Pilgrim. This man died in Spartanburg County, South Carolina and thankfully left a will naming children by two apparent marriages. The children from his first marriage (to Jennet Woodruff) received token legacies, while children from his second marriage to Nancy Pilgrim inherited the bulk of his estate. This will was written on 11 July 1835 and proved 11 July 1835 in Spartanburg County, South Carolina.

NOTE: This post will be long, so I will separately post a full transcription of Samuel Woodruff’s will.

The 1830 census helps a bit here, as Samuel Woodruff was called “Esquire” in the enumeration. He was aged 60-69 and the eldest female was aged 50-59. They were the only two family members in the household, but Samuel’s listing included 14 enslaved people.

Therefore, this Samuel Woodruff was born between 1761-1770 and likely closer to 1761 as Jennet (Woodruff) Woodruff has a gravestone inscribed with a birth date of 6 September 1762 (born in Westfield, Union, New Jersey) and death date of 14 September 1800. She died at the young age of 38.

If Samuel married at age 21 and he was about 22 at the time of his first child’s birth, the child would have been born c1784.

Children by Jennet:

1. Hannah, born c1784; married Mr. Pilgrim
2. Phebe, born c1787
3. Joseph, born c1791, per 1850 and 1860 census records
4. Moses, born c1793

Children by Nancy:

1. Aaron, but not found in any census from 1840 onward unless he is the Aaron Woodruff in Surry County, North Carolina in 1830, aged 30-39 years old. If so, then Aaron is a son of Jennet, not Nancy.
2. Amos, born c1801, Spartanburg County, South Carolina; died 1882, Lamar County, Texas; married Levina Bobo, c1823, probably Spartanburg County, South Carolina
3. Richard, born 28 December 1812; died 19 June 1892, Spartanburg County, South Carolina; married Elizabeth (MNU). He became a Baptist minister.
4. Gideon, born 1811-1820; may be the man living either in Surry County, North Carolina or Taliaferro County, Georgia
5. Rebecca; married Mr. Bobo; may be Rebecca, born c1816 married to Manly Bobo and living in Union County, South Carolina in 1850
6. Isaac, born 10 September 1806, Spartanburg County, South Carolina; died 18 August 1855, Spartanburg County, South Carolina; married Maria, c1828

Well, this is pretty good proof of Joseph’s father, isn’t it? Wills don’t lie, at least not most of the time. The answer to my question is yes AND no. Here’s why:

While picking through the land deeds of Spartanburg County, hoping to find out more about Joseph Woodruff’s life before he left South Carolina around 1815 (he begins appearing regularly on the Hopkins County, Kentucky tax lists from 1816+) for Kentucky, I came across Discovery #2, which I actually quickly wrote off and didn’t even save an image.

A Thomas Woodruff filed notice among the deeds that he was indebted to Joseph Woodruff, SON OF NATHANIEL (!)  for the sum of $1500. However, Joseph of Hopkins County was born no earlier than 1790 and this deed was recorded in 1809. The maximum age Joseph could have been was 19 AND $1500 in 1809 is worth about $30,000 today. Nathaniel Woodruff’s son, Joseph, was clearly older than 19 and a man of very comfortable means.

My third discovery is a bit more problematic. Joseph Woodruff of Spartanburg County left a will dated 22 September 1817 and proved on 18 December 1817.

Will of Joseph Woodruff, 1817
Spartanburg County, SC WB A:124-125
Source: FamilySearch

I will share a full transcription of the will in a later post, but, right now, the important section is the last paragraph on page 124 and the first two lines at the top of page 125:

. . .And if there should be a balance yet undivided it to be equally divided between my wife Anna Woodruff my sons Samuel & Thomas & Caleb Woodruff together with my daughters Polly Allen, Eunice Sparks Sally Hendrix, Elizabeth Allen & Anna Woodruff, & my son Joseph Woodruffs lawful heirs, the part of my son Joseph Woodruffs children to remain in the hands of my executors till they think proper to dispose of it for their use. I give to my son Joseph Woodruff two dollars.

I do hereby nominate & appoint John Crocker, & Nathaniel Woodruff son of Thomas Woodruff as my executors. . . .

At first, the text in blue made me think this Joseph’s namesake predeceased him, but my heart stopped for a second when I read the line in red – Joseph was clearly still living and probably had minor children since the executors were to keep control of his children’s inheritance.

The 1820 census shows not one, but two Joseph Woodruffs in Spartanburg County, both aged 26-44 and both with minor children. My husband’s Joseph had been living in Hopkins County, Kentucky by 11 October 1816, the date on the county tax list, and at least 14 months before this Joseph Sr. wrote his 1817 will.

From the wording of the will, I think Joseph Sr. realized his son wasn’t good at managing money and perhaps had financially bailed him out in the past. He also didn’t want to disinherit his grandchildren so he left their bequests in the hands of executors, who could make sure a bill got paid.

Because Joseph in Kentucky amassed a fair amount of land and I’ve not come across his name in court records for debt, I tend to believe this Joseph’s son was one of the two men still in South Carolina in 1820.

Readers, what do you think? Am I correct in believing that this point that Joseph Sr.’s son, Joseph Jr., and Joseph’s children were living locally in Spartanburg County and not in Hopkins County, Kentucky?

Joseph Woodruff of Hopkins County, Kentucky appears to be the son of Samuel Woodruff and Jennet Woodruff of Spartanburg County, North Carolina.

Here is the proposed family tree for the Woodruff family that I am trying to document:

Woodruff Family Tree

As you can see, it will take a while for me to gather documents to prove these lines. On the surface, I haven’t found any conflicting evidence pointing to errors in this lineage, but time will tell.