Bennett was the son of George Holloway and Elizabeth (Unknown) of York Co, VA. He married Rebecca "Becky" Ballard date unknown in Mecklenburg Co. He passed away about May 1815 when his last will was proven in Mecklenburg Co.
Last Will
Bennett's last will was witnessed on 9 Dec 1809 and proven in court on 15 May 1815 [1]:
In the name of God amen I Bennett Holloway of the County of Mecklenburg and State of Virginia being of perfect mind & memory so make and ordain this my Last Will and testament
Imprimis, I will that my interest in the land in Prince George County and in the County derived by my brother John at his death subject to the life estate of his widow be sold at the death of his said widow and the proceeds of such sale be equally divided between my sons John and David Holloway ------
Secondly I give & bequeath to my son James Holloway and his heirs forever the land and plantation on which I live, subject to the life estate of my wife.
Thirdly I give and bequeath unto my daughter Lucy Wright one feather bed and furniture to her and her heirs forever, and to Nancy Holloway one feather bed and furniture to her and her heirs forever and to Martha Bailey I give also one feather bed & furniture to her and her heirs forever -----
Fourthly I will that all my personal estate be left together except the beds aforesaid, willed away, and the plantation for the maintainance [sp] of my wife and daughter Nancy and the proceeds of the crops if any I give to my son James after the maintainance [sp] of his mother and sister -----
Fifthly I will that at the death of my wife that the whole of my negroes be equally divided between my children & their heirs , and that the stock go of every kind be sold and all my other personal property , and the money arising from the sale thereof be equally divided amongst my children or their heirs.
Lastly I nominate my son James Holloway executor to this my last will and testament hereby revoking all former Wills by me made. In testimony whereof I have hereunto set my hand and affixed my seal this ninth day of December 1809.
Signed Sealed and acknowledged his mark Bennett Holloway
In presence of George Small, William Holloway Junr
At a court held for Mecklenburg County the 15th day of May 1815
This will was presented in court and proven by the oaths of George Small and William Holloway junr Witnesses thereto & ordered to be recorded
Additional Timeline of Events
Below is an incomplete timeline of records currently sourced for Bennett Holloway.
1759
Bennett received 177 acres from his father's estate in Lunenburg Co which later became part of Mecklenburg Co. Bennett and Henry Deloney were executors on the estate. John Ballard, John Speed and Joseph Dobson were witnesses.
To my son Bennitt Holloway - 177 acres, joining where Harris lives.
7 Feb 1760
Bennett Holloway is appointed surveyor of the road whereof George Holloway was the late surveyor. And it is ordered that he together with the assistance that assisted the said George on the said road do forth with clear and keep the same in repair according to law [2]
1 May 1760
Bennett Holloway guardian of Thomas and Ann, minor orphans of George Holloway deceased, exhibited and made oath to an account against the said orphans estates which is ordered to be recorded [3]
5 Dec 1760
Return on the account of George Holloway's estate shows that Bennett Holloway received payment of 1 pound, 7 shillings and 9 pence [4].
7 Apr 1761
Bennett guardian to Thomas and Ann, minor orphans of George Holloway deceased. The given name Ann is presumed an interchangeable nickname for sister referred to as Nancy in other records [5].
17 Feb 1763
Bennett Holloway deeds 167 acres in St. James Parish to John Ballard, Jr. for the sum of 150 pounds current money of Virginia [6].
Oct 1774
Bennett bought additional land in Mecklenburg County from his brother John of Prince George Co, VA next to his brothers James and William Holloway in 1774: "Page 394. Oct 26, 1774 from John HOLLOWAY of Prince George County, to Bennett HOLLOWAY of M, for 50 L, about 177 acres in M on the Church Branch and bounded by the lands of James HOLLOWAY, MAYHO'S (MAYO'S?), Benjamin FERRELL, William HOLLOWAY, and the said John HOLLOWAY'S line that he purchased of George HOLLOWAY, being a tract of land given to said John HOLLOWAY by George HOLLOWAY, dec'd. Signed - John HOLLOWAY. Wit - George TARRY, John BROWN, Robert MUNFORD, Henry DELONY. Recorded Mar 17, 1775."[7].
after Mar 1782
After the death of Bennett's brother John, the siblings appeared in court to divide his estate [8][9]:
In the case of William Holloway, Burnett (Bennett) Holloway, Dicey Cox (formerly Holloway), and Nathan Winkfield and Nancy his wife (formerly Holloway) VS James Holloway and heirs, devisees and representatives of George Holloway, dec'd, the defendents are found to be not inhabitants of this commonwealth, and are to appear at February Court next.
In case of Holloway et als VS Holloways, commissioners are to make sale of 1/2 of land called "Coutts".
Jul 1787
Becky Holloway was lent enslaved persons from her father's estate [10].
I lend to my daughter Becky Holloway a negro woman named Reib and her children Charlotte, Judy and Doll and a negro man named Charles during her life and at her death I direct the said negroes and the increase of the females to be disposed of by my executor in such manner as he may thing will best contribute to the support of my grandchildren by my said daughter Becky until her youngest surviving child shall arrive at lawful age and at that time that the said negroes and the increase of the females be equally divided amongst my said daughters children to whom and their heirs I give them forever. I also give to my said daughter Becky a good feather bed and furniture.
Mar 1790
Bennett listed enslaved persons on his property tax named: Will, Reab, Charlotte, Lott [11].
11 Apr 1791
An indenture of trust between Robert Pennington of the one part and John Holloway trustee in trust for John McRae & Co. of the other part was proved by the oath of Bennett Holloway a witness thereto and is ordered to be recorded [12].
9 Dec 1809
Bennett's last will was witnessed by George Small and William Holloway, Jr. [1]
25 Nov 1811
James Holloway submits an inventory and account of sales in the property of Bennett Holloway to probate court in Mecklenburg County. Of note is that this took place three and a half years before Bennett's last will was proven in probate court [13].
15 May 1815
Bennett's last will was proven at probate court in Mecklenburg County by the oaths of George Small and William Holloway, Jr. [1]
Research Notes
Errata in Biographical Sketches
In a Starling/Sterling genealogy book (Sterling A. M., 1909, p. 1059), the father of Maj. John Holloway and husband of Rebecca Ballard is incorrectly specified as John rather than Bennett[14].
ANNE STARLING (William, William), b. Sept. 21, 1777; m. in Mecklenburg Co, Va., Maj. John Holloway, b. In 1761, son of John and Rebecca (Ballard) Holloway. He was a soldier in the Revolution; removed to Henderson, Ky., where he was an extensive planter and owner of many slaves. He was a justice of the court of quarter sessions in 1802 and sheriff of Henderson Co., 1823-24. He d. Feb 2, 1825; Anne d. Aug. 2, 1840.
This mistake seems to have propagated in numerous online trees leaving the descendants of Maj. John Holloway and Anne Starling with a brick wall in identifying a non-existent John Holloway who married Rebecca Ballard in Mecklenburg Co, VA. It is highly unlikely that Bennett was ever referred to as John as he had a well-documented brother named John without issue who left a sizable estate in Prince George Co., Virginia to his widow and provisionally his siblings at her death or remarriage.
↑ Sterling, Albert Mack. “THE STARLING FAMILY OF VIRGINIA.” Essay. In The Sterling Genealogy, Volume II : William Sterling of Haverhill, Massachusetts II, p. 1059. The Grafton Press, New York, 1909. Citing erroneous identification of the parents of Maj. John Holloway as "John and Rebecca (Ballard) Holloway" instead of "Bennett and Rebecca (Ballard) Holloway".
Lunenburg County Virginia, Court Order Books, Vol. 9, p. 143; 1 May 1760, Bennett Holloway guardian of Thomas and Holloway orphans of George Holloway deceased, exhibited and made oath to an account against the said orphans estates which is ordered to be recorded.
Genealogy and history of William Starling, his family, ancestors, and descendants, The Sterling Genealogy: volume 2 : William Sterling of Haverhill, Massachusetts, in North America, Chapter: The Starling Family of Virginia and Kentucky, in Family Histories, 1500-2000, through Ancestry.com. https://search.ancestry.com/collections/61157/records/1790356. Accessed 3 Feb 2022.
WikiTree profile Holloway-276 created through the import of Clayton Burton_2009-10-26.ged on Jul 4, 2011 by Clayton Burton. See the Changes page for the details of edits by Clayton and others.
WikiTree profile Holloway-523 created through the import of Cato Family Tree_book_EN.ged on Sep 21, 2011 by Linda Cato. See the Changes page for the details of edits by Linda and others.
WikiTree profile Holloway-537 created through the import of Cato Family Tree_book_EN.ged on Sep 21, 2011 by Linda Cato. See the Changes page for the details of edits by Linda and others.
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DNA Connections
It may be possible to confirm family relationships with Bennett by comparing test results with other carriers of his Y-chromosome or his mother's mitochondrial DNA.
Y-chromosome DNA test-takers in his direct paternal line on WikiTree:
Holloway-6033 and Holloway-276 are not ready to be merged because: As far as I can tell the only source of a John Holloway marrying Rebecca Ballard in Mecklenburg, VA comes from a book focused on Starling family history that may have skirted an important detail. All other signs point to Major John Holloway being the John named in the last will of Bennett Holloway.
The only known secondary source for the parents of Maj. John Holloway being John Holloway and Rebecca (Ballard) Holloway is a Starling/Sterling genealogy book from 1909.
While the evidence that his father was instead Bennett Holloway is still incomplete, it's far stronger given surrounding records than the passing sentence from a book written 1909 focused on Sterling/Starling research. We can mark it uncertain but it's far more likely to be Bennett than John.
Additionally, we have WikiTree profiles with matching Y-DNA from descendants of Bennett Holloway and his brother William Holloway. A male-line descendant of Maj. John Holloway would be able to prove/disprove his descent from Bennett Holloway. I've located living male-line descendants and in the process of showing them the utility of it.
As noted on the profile, Bennett's and William's brother John died without issue. A Y-DNA match in this family would be enough evidence to prove that Maj. John was the son of Bennett Holloway he named in his last will.
The only known secondary source for the parents of Maj. John Holloway being John Holloway and Rebecca (Ballard) Holloway is a Starling/Sterling genealogy book from 1909.
While the evidence that his father was instead Bennett Holloway is still incomplete, it's far stronger given surrounding records than the passing sentence from a book written 1909 focused on Sterling/Starling research. We can mark it uncertain but it's far more likely to be Bennett than John.
Additionally, we have WikiTree profiles with matching Y-DNA from descendants of Bennett Holloway and his brother William Holloway. A male-line descendant of Maj. John Holloway would be able to prove/disprove his descent from Bennett Holloway. I've located living male-line descendants and in the process of showing them the utility of it.
As noted on the profile, Bennett's and William's brother John died without issue. A Y-DNA match in this family would be enough evidence to prove that Maj. John was the son of Bennett Holloway he named in his last will.