Theories I've found
on Benjamin Bolling's Ancestry

Updated: 6 October 2002

These pages will change as I expand each theory or find new ones.


1. It has long been asserted that Benjamin Bolling, born June 30, 1734, was the son of John Bolling and Elizabeth Blair Bolling..One of 19 sons. I have found no proof of this anywhere.

2. I have read that he was the brother of Mary "Molly" Bolling who married "old" Andrew Baker but no one can prove who her parents were????

3. Illegitimate son of Mary "Polly" Bolling, who died giving birth to Benjamin, and Isham Randolph. Whether this means General Isham Randolph or his son, Isham, b. in 1714, I have no idea. General Randolph died in 1742, which would exclude him from being the father of someone born in 1744.

The Randolph's and Bollings do have a long history though and General Isham Randolph was the brother of Mary Bolling Fleming's brother-in-law, Col. Richard Randolph.

This Mary Bolling, sister of John Boling who married Elizabeth Blair and wife of Col.John Fleming is a possibility for Benjamin's mother. Col. Fleming died in 1756 but Mary died in 1744, possibly giving birth to Benjamin? This would make him 10 years younger than previously thought but age descrepancies happen all the time. This theory also says his name was John Benjamin Bolling, he was raised by his grandmother "Betsy" Bland (Elizabeth Blair Bolling m. Richard Bland after her husbands death in 1757) and that he had a sister named Jane Jefferson.

The only Jane Jefferson I can find in this time period is Jane Randolph, daughter of Isham, wife of Peter Jefferson, and mother of President Thomas Jefferson.

According to the theory, Benjamin was supposed to have returned to Virginia to visit his grandmother but she was already dead so he ended up working for his sister, Jane Jefferson, helping her to build a house. Elizabeth "Betsy" Bland died in 1775 and Jane Jefferson died in 1776 while living at Monticello, the home of her son, Thomas Jefferson. Construction began on Monticello in 1769 and lasted for many years, so Benjamin could have worked on it. But..if he worked on Monticello wouldn't family tradition have mentioned that instead of just saying that he helped his sister build a house? Monticello was not just a house, it was the house of the President!

However, if this theory is true, he would have been a half brother to Jane...(coincidentally, General Isham Randolph had a daughter named Dorothea. Dorothea is an asserted twin of Benjamin and daughter of John and Elizabeth Blair Bolling...I find this little tidbit fascinating!)

The name descrepancy ("John" Benjamin Bolling) could explain why we can't find any records of him before 1800 or so. There are plenty of "John" Bollings in Va., NC and SC. Could Benjamin be one of them? I know that Southern families used first names for legal documents even though people often went by their middle names. I've not found any documentation pointing in that direction with Benjamin though.

The Randolphs, Bollings and Flemings lived within close proximity of each other so there is every possiblity that Mary could have had a close relationship with Gen. Isham Randolph - or any of his sons.

Note #1: Grantee: Randolph, Thomas. Date: 9 February 1727. Location: Henrico County. Description: 400 acres on the south side of James River; begg. at Thomas Attkinsons or John Rights lower corner on the South side James River, opposite to Major Bollings plantation in his Island. I am not sure who this Thomas is. Some researchers list Gen/Col. Isham Randolph's first name as Thomas?

Note #2: from Library of Va., Land Grants - Grantee: Randolph, Isham. Date 19 June 1735. Location: Goochland County. Description: 28 acres, 1 r., 28 po., being in James River opposite to Fleming’s Rock Castle Tract being an Island. Source: Land Office Patents No. 15, 1732-1735 (v.1 & 2 p.1-522), p. 525 (Reel 13).

Note #3: Grantee: Bolling, John. Date: 6 May 1727. Location: Henrico County. Description: 800 acres or the north side James River on the back of Mr. Fleming’s Rock Castle tract. Source: LVA Land Grants, Land Office Patents No. 13, 1725-1730 (v.1 & 2 p.1-540), p. 73 (Reel 12).

On the Pocahontas Descendant chart at Pocahontas Descendants, David Morenus shows 8 children for Mary Bolling Fleming, although only 7 are named. Who is the other son?

Conclusion: #1 If Benjamin was born in 1734 and his mother died at his birth, he can't be the son of Mary Bolling Fleming, who died in 1744 - but could be the son of another Mary Bolling and General Isham Randolph. But which Mary Bolling?

Conclusion #2 If he was born in 1744, the illegitimate child of Mary Bolling Fleming, his father could not have been General Isham Randolph, who died in 1742, but could be Isham, the son of General Randolph. I am currently doing research on this Isham Randolph.

This Bolling/Randolph theory is supposed to come from some papers that Jeremiah Bolling wrote but I have not seen those papers.

There is another Mary Bowling possibility. She married William Eaton in Stafford Co. Va. in 1935. I can't find any parents for her. And I'm not sure if this is the same William Eaton in the Eaton's Militia Muster of Granville Co. NC in 1754. There is a Benjamin Bowling on the Muster also. Is he a son of this Mary Bowling born before she married William Eaton?

4. He is the son of Thomas Bolling/Boulding of the "Swan". The Bolling Family Association is leaning in this direction after DNA testing on Col. Robert Bolling's proven descendants. This Thomas Bolling emigrated to Maryland then to Lunenburg Co., Virginia. However, after searching all the Bollings in Maryland, (including a James that migrated to Va.) I can find no link between the Maryland Bollings and Benjamin.

5. He is the son of Edward Bolling and a Slaughter woman. Edward is a son of Robert Bolling and his 2nd. wife, Anne Stith. I can find no proof of a marriage for Edward anywhere. Nor any proof that this Slaughter/Bolling wife took her son Benjamin to NC where he married Charlotte Ward and later had Benjamin b. in 1734. This would make Benjamin a "White" Bolling and not a descendant of Pocahontas.

6. I have found a reference to a will for a John Bolling at the LVA:

Bolling, John. Date 1744 Source Ac 22483 (Personal Papers, Tighe) Will dated 30 November 1744 Will proved 13. March 1744/5 Note: Part of index to wills not listed in Virginia Wills and Administrations, 1632-1800 (Torrence). Collection: Virginia wills and administrations. No County listed and no other information. . Is it possible Benjamin descends from this John Bolling? Does anyone know who this John Bolling is or have a copy of the will?

7. 1741 N.N. Land Grant May 15 Miss Mary Bolin, Prince William Co. (formed from Stafford and Prince Geo. Counties in 1731.) 330a adjoining land of Elzy, Keen and Carter (LVA N.N. Land Grants ~ Blauser Card #188). Does anyone know who this Miss Mary Bolin is?


1. Benjamin was supposed to have married a Martha "Patsy" Phelps on ____ in Albemarle Co., Va. Does anyone know where I can find proof of this? Who were her parents? I have found two references at the LVA to a Phelps family in Albemarle Co:

Patent: Grantee: Phelps, James. Date 16 August 1756. Location: Albemarle County. Grantee(s): Phelps, James and Phelps, William. Description: 400 acres on both sides of a branch of Wreck Island Creek.

Patent: Grantee: Phelps, James. Date 16 August 1756. Location: Albemarle County. Grantee(s): Phelps, James and Phelps, William. Description: 400 acres on a western fork of Wreck Island Creek.

Anyone have any further information on this family?

2. His second wife was Charity Larimore. According to the Bolling/Randolph theory, Benjamin married Charity/Chrissie/Elizabeth on the Edisto River in SC and they had their son Jeremiah there. I cannot find any parents for Charity or proof of their marriage. Nor is there proof of Jeremiah's birth or his marriage to Sarah "Sally" Ward.

Siblings - the "Blue" Bollings

There are 7 proven descendants of John Bolling and Elizabeth Blair Bolling. Those 7 are "Red" Bollings, descendants of Pocahontas. There are 7 other "Red" Bollings that died young. There are 12 "Blue" Bollings, whose ancestry is unknown at this time.

1. Meotaka
2. william - cousin of Benjamin?, son of Thomas Bolling and Elizabeth Gay? or son of Anne Bolling and James Murrary?
3. Elizabeth - cousin of Benjamin? daughter of Thomas Bolling and Elizabeth Gay? (twin of William?)
4. Jared
5. Martha - cousin of Benjamin? daughter of Martha Bolling and Thomas Eldridge?
6. Dorothea (with twin 7. Benjamin)- actual daughter of Isham Randolph and half sister to Benjamin?
8. Jane - actual daughter of Isham Randolph and half sister to Benjamin?
9. Rodney
10. Rolfe - cousin of Benjamin?, son of Martha Bolling and Thomas Eldridge?
11. Powhatan - cousin of Benjamin, son of Robert Bolling and Mary Burton?
12. James - cousin of Benjamin, son of Anne Bolling and James Murray?

Is it possible that all but Dorothea and Jane could be grandchildren of John and Elizabeth Blair Bolling and probably 2nd cousins of Benjamin? Possibly they all lived with John and Elizabeth at one time or another and people assumed they were all their children? Dorothea and Jane look to be legitimate children of Isham Randolph and his wife Jane Rogers, and therefore 1/2 sisters of Benjamin.

I can find no explanation for linking Meotaka (unless she was daughter of John and his 1st wife, Elizabeth Lewis),Rodney or Jared to Benjamin.

In Samauel Bollings bible, he says his parents are William Bolling (son of John and Elizabeth Bolling Blair) and Amelia Randolph (daughter of Richard Randolph of Anne Meade). William Bolling, son of Thomas Bolling and Elizabeth Gay, did marry Mary Randolph (daughter of Richard Randolph and Anne Meade) but her name was not Amelia and they did not have a son, Samuel - not that I can find anyways. According to research done by A. D. Smith, of SC., Samuel does descend from a William Bolling but he and I believe this William Bolling was the son of James Bolling/Boulding of Pittsylvania Co. Va. I have not been able to connect him to Benjamin. These Bollings may be descendants of Thomas Boulding of the "Swan".

In a letter from Hosea Bolling (Jeremiah's son, Benjamin's grandson) to Jason Walker Bolling, Hosea says that his grandfather had a brother named Justice and that he "saw the two old men together" numerous times. Because Justice was so much older than Hosea's father, Jeremiah, could Hosea have mistakenly thought he was a brother to Benjamin instead of a half brother to his own father, Jeremiah? It's my belief that Justice was probably a son of Benjamin from his 1st. marriage but without documentation it's just another assumption.


There are numerous lists of children for Benjamin from both marriages. None of the lists seem to be the same. I've combined all the children of each wife from all the lists to see what I could come up with. None of the birthdates jive with Benjamin being born in 1744. Possibly researchers have just estimated the children's birth years based on Benjamin being born in 1734.

with Martha "Patsy" Felts/Phelps:

1. Justice Bolling - m. Martha "Patty" Baker. Issue: Solomon. Solomon's issue: Sarah. Sarah's issue: Henry Clay Bolling

2. Benjamin Bolling b. 1754, m. Sally "Talitha" Hancock.

3. John Bolling b. 1755 in Henry Co. Va.

4. William Bolling b. 1755/57 in Henry Co. Va.

5. Jesse Bolling b. 1758, m. 1st. Polly Green and 2nd. Mary Pennington

Because of the 6 year time frame between children, I believe Justice belongs in here.

6. Delaney Bolling b. 1764.

7. Hannah Bolling b. 1766 m. Solomon Osborn. Does anyone have proof that she was Benjamin's daughter?

8. Elizabeth Bolling b. 1767. This Elizabeth is said to have married William Short. Martha is said to have died at the birth of Elizabeth in Rowan Co. NC.

with Charity Larimore:

1. Jeremiah b. 1782, m. Sarah "Sally" Ward.

Note: There is a 15 year gap between his last child with Martha and his first child with Charity, leaving open the possiblity that there were children born to Benjamin and Charity before Jeremiah, or possibly even another marriage though I've found no hint of a wife other than Martha and Charity.

Other children's names mentioned are Charity, Levi, Issac, Bennett/Barnett, Isham and James. I have found no documents linking them to Benjamin.

As you can see, I've hit a brick wall! This is not unusual in genealogy as I'm sure you all know. But if you have any information on the contents of the information herein, please email me. Or leave a message on my message board.

Thanks! Barb