Reflections concerning Isaac Holleman, 1818-1898 ca

 by Glenn N. Holliman

Daffodils tell a Story

On March 12, 2022, a Holleman/Holliman family group, all descended from ancestors of Isle of Wight County, Virginia, finished a late lunch in Windsor, Virginia. It had rained 'cats and dogs' that morning but after the sky had emptied several inches of rain, a nasty, windy cold front moved in, and later a wet snow fell.  We were a three, sometimes a four, car convoy visiting Holleman ancestry sites, on a blustery day in late winter.

Above, at an earlier stop before lunch near Windsor.  Susan White, our leader, shivering in blue, Tammy Hunt, Sandi Royal, Kimberly Holliman and her father Paul Holliman listening to a lecture at a century old country store by Jim Henderson (not visible) of the IOW Historical Society.  

Refreshed by a quick meal, our convoy headed east on Old Suffolk Road. The rain eased, although not the wind chill.  We turned south on Tyler Road, drove a half mile or so, stopped at the Tyler Cemetery.  

Here we visited the resting places of the African-American Hollemans, often spelled Holliman, many descendants of Isaac Holleman.  

Isaac Holleman was our reason for this trip.  He had been born a slave into the household of Josiah Holleman of Mill Swamp, IOW, in 1818.  His story has intrigued me since I heard it in 2012 from Sandi Royal, a descendant of Isaac.

Isaac's great grandson, Nonnie Holliman, pictured here visiting his grandfather's resting place, was in our group, as well as others who descended from Isaac.  Nonnie, retired from Federal service,  drove all the way from his home in Syracuse, New York to make this pilgrimage to the town in which he grew up.  

The genealogist who had arranged the trip, Susan White, of Richmond, descendent of Josiah, has gathered in the past year a monumental amount of research on Isaac and his two wives, Malinda Pretlow and Ann Gray. 

Susan has written the past three blogs on Isaac and his incredible story.  She is an often visitor to the Library of Virginia, the Virginia Baptist Historical Society Library, and the archives of IOW county.  Those of us studying the Hollyman families in Virginia owe her a great debt of gratitude.

Utilizing her research and that of historian Jim Henderson of IOW Historical Society who also accompanied us, I add my own reflections and tip my hat to both of them.

At the Tyler Cemetery, Kimberly Holliman, Sandi Royal, this writer, Tammy Hunt and Doris Knox

The water table in this part of southeast Virginia is close to the surface hence the concrete tablets to secure the grave sites.  

Isaac escaped bondage during to the Civil War and found sanctuary at Fortress Monroe, a Union outpost. There he must have met and married the mysterious Ann Gray.  Destitute after the war and with children from his first wife, Malinda, and now children with Ann, somehow he was able to purchase a 50 acre farm in 1871.  Susan believes he died there before 1899 and his wife, a few years later.  In her research Susan discovered the location of the farm near Tyler Cemetery.

Are this biracial couple buried in Tyler Cemetery?  No, that is not their resting place.  Nonnie, who had spent time on the farm in childhood (it stayed in the Holleman family until 1954), believes the couple is buried on their farm.  

We boarded our automobiles, studied our maps and headed further south along Tyler Road, past the turn off at Dunston Road, and drove a bit further.  The farm had been purchased by the railroad and now the land along Tyler was now brush, trees and shrub.  We could find no entrance into where we knew from the map that the farm had been located.

And then we spotted the daffodils.

 

Daffodils are not native to North America.  They have to be planted.  According to author Kelly Gamey, who photographs and writes of forsaken southern properties, a clump of isolated daffodils in the spring are 'ghost gardens', bulbs buried in previous decades by former inhabitants of abandoned sites.  You might check out her site at kelly@theforgottensouth.com.

There were no other daffodils along the road.  This had to be the lost entrance to the Isaac and Ann Gray farm.  Somewhere in the bush probably lay the foundations of a home and graves.  But we were not equipped for an exploratory hike in the marshy woodlands that cold afternoon. 

We stopped, took photos, and chilled as we were, called it a day.  I rode with Susan, our driver and historian, and Sandi and Nonnie, all of us returning to Richmond.  We said goodbye to Tammy and Doris of Southampton County.  And also Paul, Teresa and Kimberly Holliman, residents of Williamsburg and alumni of our 2019 Hollyman excursion to England.  They ferried across the James River, coming and going to be with us that day.

On the way back it snowed several inches and the temperature kept dropping.  But our hearts were warmed by what we had seen and heard that day.

And more on the trip in the next blog as we explore further the life and times of Isaac Holleman.....

The Saga of Isaac and Ann Gray Holleman, Part 3

 

The story of the biracial couple of 19th Century Isle of Wight, Virginia continues, written by Susan G. White (pictured right), a family historian known for her research and careful conclusions. We are grateful to her for sharing her insights and gathering information thoughtfully from the ancestors of this courageous couple. - Glenn N. Holliman

Enter Ann Gray, a White woman. Ann has been the subject of much speculation and interest in current-day Holleman researchers.  For generations, Black Hollemans have told of Isaac and Ann’s complicated relationship in their oral history, that Isaac and Ann fled from her angry family in their initial love.  

White Holleman researchers have tried to connect Ann with Gray ancestors who were closely connected with Josiah Holleman, or to other Ann Grays in Isle of Wight, but to no avail.   Sandi Royal, a descendent of Isaac’s son Joshua, Denise Keeter Goff, an excellent Holleman researcher, and I worked hard this past summer of 2021 to track down Ann’s parents.  

Sandi finally summed it up perfectly, “We will probably never know who Ann’s parents were.”  Be that as it may, somehow, Isaac and Ann met and found a life together.

Above, Glenn N. Holliman and Sandi Royal discussing the Isaac and Ann Gray Holleman story in 2012 in Chester, Virginia.

We know of Isaac and Ann’s life first by way of Freedman’s Bureau records.  Isaac petitioned the Freedman’s Bureau in October 1865, from Fort Monroe, Virginia, to request money for him, Ann, and his three children Robert, Ada, and Moses, to return to Nansemond county, Virginia, to “escape destitution.”  

He also requested help from the Bureau that his son Robert Holleman be reimbursed for the money owed to him for working for the “Widow Binford.”  Mrs. Binford and her husband lived one dwelling away from Malinda Pretlow in the 1860 Southampton County census.  Isaac was working to get what he felt he was due after the war, in order to survive.  

We can wonder how it was that Isaac, Ann, and the 3 children ended up at Ft. Monroe?  The fort was under Union control during the Civil War, and commanded by General Benjamin Butler.  

The general famously would not return slaves who had fled to Ft. Monroe to Confederate owners; he called the slaves “contraband of war.”  Large numbers of slaves found the destination of Ft. Monroe to be sanctuary, and we can guess that Isaac and family were no different. 

In her famous book on the history of Isle of Wight County, Helen Harverty King wrote the following:

'The county was in desperate circumstances by the end of 1863. The season had been bad, almost the entire slave population was gone, the call came for more recruits for the army, the insecurity of persons and property was made greater by frequent enemy visits and there was a great scarcity of necessities for life on the home front."

 Isaac’s three children with his first wife Malinda Pretlow were Robert, Ada, and Moses, all who have been well documented.  Robert married Cassandra Daughtry, and had 10 children; he stayed in the Isle of Wight area.  Ada  married Jacob Ely, and after she died, Jacob married her half-sister Lucerne Holleman, a daughter of Isaac and Ann.  Moses married first Eugenia Randal/Randolph, and after she died, he married her sister, Ann Eliza Randal/Randolph.

Above on an excursion in Isle of Wight County, Virginia in 2012 are left to right: Tammy Hunt, Cyndi Barnett, Doris Knox, Robert Royal and in the background, Sandi Royal. Tammy is a descendant of Isaac and Malinda; Cyndi, Doris and Sandi all are descendants of Isaac and Ann Gray Holleman. Robert is Sandi’s husband.  They are all standing on Proctor’s Bridge overlooking the Blackwater River, not far from the ancestral farms of the Binfords, Pretlows and Hollemans.

Census records have been fruitful in uncovering Isaac’s story, with one exception.  We cannot find Isaac and family anywhere in the 1870 census that would explain where they moved to after Ft. Monroe.  

Why did they request transportation to Nansemond county, southeast of Isle of Wight, instead of back to Isle of Wight?  

All comes well, though, in the 1880 census and farm schedule, where Isaac, Ann, and family owned a 50-acre farm in the Windsor district of Isle of Wight.  They had a total of 10 children:  Luzerne, Roxanna, or Roxie, Addie Lou, Nonnie James, Isaac Thomas, Sr., Jeremiah, Joseph, Joshua Sr., John H. Sr., and Joanna. 

Recent examination of Isle of Wight land tax records revealed that Isaac paid tax on his farm located 9 miles south of the county courthouse until 1897, and we know that he fathered daughter Joanna, also in 1897.  His land entry was entitled “Holleman, Isaac, estate” in 1898, so we can safely assume he died in 1897 or 1898.  Ann shows on the 1900 census as a farmer, owning her home, and widowed.   Further land tax records continue to refer to the farm as Isaac’s estate.

This story of Isaac Holleman and his remarkable life in Isle of Wight county, Virginia, shows resilience, persistence, and honor in achieving his freedom in ways we find difficult to fathom.  

He survived slavery twice, gained emancipation, survived the Civil War, Reconstruction, and Jim Crow.  Isaac’s proximity to Fort Monroe, Virginia and Isle of Wight, Virginia illustrate the geographical, political, and historical connections of slavery in our Holleman family.

Isaac’s children’s stories continue, with descendants Black and White uncovering and sharing them.  Perhaps we can share them later. -Susan G. White 

Isaac Holliman - A Story of the Old South, Part III

by Glenn N. Holliman

Who were Ann Gray Holliman's Parents?

The oral family tradition is compelling and dramatic.  Perhaps during the Civil War, a man held in bondage, one Isaac Holliman, ran away with a white woman, Ann Gray, evidently half his age.  Her parents were furious, and the couple escaped their outrage by hiding in the forests or swamps of southeast Virginia.

Below the Chapel Grove United Church of Christ in Windsor, Virginia where Isaac and Ann Holliman may be buried.  Many of their descendants rest here.

Who was Ann Gray?  Who were her parents and where did this family live?  Oral tradition places both Ann and Isaac as natives of Isle of Wight County, Virginia.  Grays and Holymans were both early settlers of Isle of Wight, and their ancestors live near each other even today.

We have some hints but only a very few....

In a published Isle of Wight will, one Ann Gray is recorded as a grand daughter of Josiah Holleman who died in 1847.  Josiah Holleman had a son named Wilson Holleman.  The will also lists a daughter, Virginia Gray and another grand daughter, Virginia Gray, the same name.

In the Census of 1860, a family is listed in Smithfield, Isle of Wight, of William Gray, age 40, Matilda, age 34 and among the children, one Ann, age 13.  Is this the same Ann Gray recorded in Josiah's 1847 will?   Is this the Ann Gray who will marry Isaac Holliman?  She could be as the age almost works, but, it is difficult to be certain.  As descendant Nonnie Holliman notes, this Ann is no longer with the Gray family in the 1870 Census.

As noted in the last posting, one Isaac Holliman, age 47, and Ann, age 21, and a minor, Isaac's son Robert, age 15 by a first liaison, are recorded in U.S. Freedman records in 1866.  This Ann is close to the age recorded in the 1860 Federal Census in the William Gray family.

 This couple, with increasing numbers of children, appear in every Federal census until Isaac's death before 1900.  Isaac and Ann are recorded as mulatto, that is of mixed African and European DNA.  These several censuses place the couple as living in Windsor, Isle of Wight County, Virginia which is located near the original Christopher Holyman plantation founded in the 1680s.

So here we are....

1. The above Pre-Civil War records may or may not identify Ann Gray's parents and grandfather.  Circumstantial evidence is there.  Is it enough?  It is hoped that more records can be discovered to verify parentage beyond a reasonable doubt.

2. Federal censuses identify Isaac as mulatto which begs the question - was he the biological son of a white man named Holyman, Holleman or Holliman?  After all Isaac took the name Holliman from the family that owned both him and perhaps his mother.

3. DNA testing done to date has not yet tied the European Hollimans to the African American Hollimans.  DNA from a male, directly descended from Isaac through males only, is needed to test the thesis that Isaac is descended from Christopher Holyman, 1618-1691.

4. To my knowledge no one has approached any Gray descendants for DNA testing.  Research could be done to locate persons who have Gray ancestors in Isle of Wight County.  (For DNA testing cousin Tina Peddie can provide assistance; see information below in blue.)

5. The evidence we do have is remarkable - oral tradition that Ann was the 'white grandmother', the Freedman's record of 1866 and the Federal Census records that place the family in Windsor, Isle of Wight, near the historic homes of the Grays and Hollemans.

Isaac and Ann Gray Holliman left a legacy of children and later descendants who proudly claim this remarkable couple as their 'founding family'.  From time to time, descendants gather in southeastern Virginia to celebrate their heritage and the blessings of being American.  Sandi Royal and others have published a book on the descendants of Isaac and Ann Gray Holliman.  For information on future reunions and this publication, Mrs. Royal can be contacted through this writer at glennhistory@gmail.com.

 

In the Autumn of 2012, Holliman descendants on an afternoon of discovery visited the Mill Swamp Baptist Church Cemetery in Isle of Wight, County, Virginia to learn more about our shared history and possible ancestors. Below, left to right are Christopher S. Holliman (the writer's son), Doris Knox, Cyndi Barnett, Tammy Hunt, Glenn Holliman (the writer) and Sandi Royal. 

 

 
The gravestone, pictured above, is a memorial to several Isle of Wight County 20th Century descendants of Christopher Holyman (1618-1691), of whom recent members generously gave the land for the cemetery.  More will be written on this branch of the Holleman family in future posts. 

Research work remains to be accomplished to verify if our Holliman families are genetically related.  However, it is very appropriate to state that we are related by time, place and the tides of history, and that we share in the American story!

I am grateful to the above descendants and others of Isaac and Ann Gray Holliman who have written and told me this intriguing story and encouraging additional research.  Any errors in these posts are mine alone, and I would be grateful for any additional information and/or corrections. 

Next posting....more on Isle of Wight Hollemans....

Descendants of Isaac and Ann Gray Holliman will hold a family reunion at the Wakefield Conference Center and Campground, Wakefield, Virginia August 10 and 11, 2013.  Cost is only $35.  For information, contact Tammy Hunt at hunttl_sept2571@yahoo.com.
 
Have questions about Holliman family history? You are invited to join the Hollyman Email List at Hollyman-Subscribe@yahoogroups.com and the Hollyman Family Facebook Page located on Facebook at "Hollyman Family". Post your questions and perhaps one of the dozens Holyman cousins on the list will have an answer. For more information contact Tina Peddie at desabla1@yahoo.com, the list and Facebook manager for Hollyman (and all our various spellings!). Mrs. Peddie can assist also in any DNA research.

Since early 2010, I have been publishing research and stories on the broad spectrum of Holliman (Holyman) family history at http://hollimanfamilyhistory.blogspot.com/ . For stories on my more immediate family since the early 20th Century, I have been posting articles since early 2011 at http://ulyssholliman.blogspot.com/ .

Let's save the past for the future! If you have photographs, letters, memorabilia or research you wish to share, please contact me directly at glennhistory@gmail.com. Several of us have an on-going program of scanning and preserving Holyman and related family records. Write please and tell us of your items. Thanks to the Internet, we are able to scan, upload to the web (with your permission) and return the materials to you.

A seminar is to be held at the Rose Hill Inn, Fayette, Alabama, October 18 and 19, 2013 for more serious students of Holliman and related families.  Just write me for more information. GNH

  

Isaac Holliman - A Story of the Old South, Part II

by Glenn N. Holliman

A Holyman Family with Deep Roots in Virginia....

We continue the fascinating story of the family and descendants of Isaac and Ann Gray Holliman....

Below, left to right, Doris Knox, Tammy Hunt, Cyndi Barnett and Sandi Royal visit Holliman graves at Chapel Grove Cemetery, Windsor, Virginia.  All in this photograph, both living and those who have gone before, are descendants of Isaac Holliman, a former slave who had 12 children with Ann Gray, who by family tradition was a daughter of a slave owner. 

Isaac did have a son Robert W., probably born in or around 1851 by an earlier relationship with a woman named Matilda.  Tammy Hunt is descended from these first parents.


According to family records, the girls of Isaac and Anne were Anne Lou, Joanna, Luzerne, Monil J. and Rosanna.  The boys were Isaac T., James H., Jeremiah P., John H., Joseph, P., Joshua, and Nonnie J.  

Who was Isaac Holliman?  The 1880 census states an Isaac Holliman of Isle of Wight, Virginia was born in 1824 and had a wife named Ann.  Her birthday is in uncertain, born perhaps in 1832, 1845 or 1852.  

 

According to Sandi Royal, Isaac may or may not have been the offspring of his owner, whose name was Holliman.  DNA testing to this date has been inconclusive as to whether Isaac and his offspring are genetically related to the descendants of Christopher Holyman (d 1691).  However, there is not doubt that the two families are historically related by time, place and circumstance.

 

The name of the white Holliman family that held Isaac in bondage is not known with certainty although Mrs. Royal has an opinion based on careful reading of George Holleman's 1953 history of the family (reprinted by Tina Peddie and available for sale). 

 

Isaac did adopt the name Holliman, and after having fathered one child, at some point in his life 'jumped the broomstick' (married) a woman named Ann Gray, evidently during the Civil War.  Family tradition records Ann who died in 1930 as 'being the white grandmother' and tales abound of Ann being a slave owner's daughter.  The couple literally 'ran into the woods' to escape Ann's angry parents.

 

The document below, found by Hollyman historian Jeanette Holiman Stewart, was issued   October 8,1866 at Fortress Monroe, Virginia. The letter requests for Isaac Holliman, his wife, Ann, and son Robert transportation back to Nansemond County (an extinct county which bordered Isle of Wight County).  The three are identified as 'freed people' who, as were tens of thousands of former bonds people, displaced by the upheavals and destruction of slavery during the Civil War. 

Note Isaac's age is listed as 47 and Ann as 21 (which would make her born in 1845) and the stepson of Ann, Robert, is 15.  This Federal document suggests Isaac and Ann were only recently married, given her young age (if accurate) and the lack of children listed.
 

 

Next article more on this couple who defied the laws of their time to marry and found a family in post-Civil War Virginia.  And who was Ann Gray?
 

Have questions about Holliman family history? You are invited to join the Hollyman Email List at Hollyman-Subscribe@yahoogroups.com and the Hollyman Family Facebook Page located on Facebook at "Hollyman Family". Post your questions and perhaps one of the dozens Holyman cousins on the list will have an answer. For more information contact Tina Peddie at desabla1@yahoo.com, the list and Facebook manager for Hollyman (and all our various spellings!).

Since early 2010, I have been publishing research and stories on the broad spectrum of Holliman (Holyman) family history at http://hollimanfamilyhistory.blogspot.com/ . For stories on my more immediate family since the early 20th Century, I have been posting articles since early 2011 at http://ulyssholliman.blogspot.com/ .

Let's save the past for the future! If you have photographs, letters, memorabilia or research you wish to share, please contact me directly at glennhistory@gmail.com. Several of us have an on-going program of scanning and preserving Holyman and related family records. Write please and tell us of your items. Thanks to the Internet, we are able to scan, upload to the web (with your permission) and return the materials to you.

Announcing also a "Seminar and Site" gathering October 18 and 19, 2013 in Fayette, Alabama for Hollimans and associated families whose ancestors are from that area. Space at the Rose House Inn is limited for the occasion due to a football weekend. For information, contact me at the above email. Hope to see some of you there. - GNH

Isaac Holliman - A Story of the Old South, Part I

by Glenn N. Holliman

Last year in this space, Sandi Royal of Virginia, told the family story of her great great grandparents, one a former slave and one a slave owner's daughter, who defied the severe mores of the 1800s, eloped, married and against social odds raised a family.  In the 21st Century descendants of this couple, Isaac and Ann Gray Holliman, gather regularly in southeast Virginia to celebrate their history and family.  In October 2012, my son, Christopher S. Holliman, and I joined several of these descendants to explore our shared history in Isle of Wight County, Virginia. 

This is a story of people connected by history and family....

As the tobacco and later cotton culture of the southern colonies and later states took hold in the 18th and 19th Centuries, some Holliman families, descendants of Christopher Holyman (who died in 1691 without owning other human beings), purchased slaves.  We know this because in their Wills, these Hollemans (of various spellings) devolved persons in bondage to their off-spring.  

Due to the lack of legally recording early births in Virginia, we have an incomplete understanding of family relations, especially so among African-Americans, most of whom were held as slaves. In addition, marriage was not legally recognized or recorded for slaves.  Indeed part of the special horror of southern slavery was that husbands were sold away from wives and children, and children from their parents.

As generations passed these African-Americans who had lost their language, their religions and their very names, adopted European names and melded the remains of their past with the emerging culture of a new United States.  Persons held in bondage took the names of the slave owners, and hence today, especially in southeastern Virginia, one will find numerous African-American Hollimans who have gone on to prosper in the New World.  

Which leads us into the story of Isaac and Ann Gray Holliman....

Below, soy bean fields and autumn wild flowers on the original farm of Christopher Holyman, who came to Virginia in 1650 from Bedford, Bedfordshire, England and farmed in Isle of Wight, Virginia until his death in 1691. 

Below some descendants of Isaac Holliman and Ann Gray on an autumn tour in southeastern Virginia to explore ancestral sites.  Right to left are Cyndi Barnett, Tammy Hunt, Doris Knox and Robert Royal, husband of Sandi Royal.  This photo was taken October 2012 on a bridge overlooking the Blackwater River in Isle of Wight County, Virginia, the area where Isaac and Ann Gray Holliman lived after the Civil War. The original Christopher Holyman plantation was established along the Blackwater River and Mill Swamp bordering Surry County.  Hollemans today of African and English descent still live in these first settlements of what became the United States.

Next posting, more of the amazing story of Isaac and Ann Holliman and their American legacy....

Have questions about Holliman family history? You are invited to join the Hollyman Email List at Hollyman-Subscribe@yahoogroups.com and the Hollyman Family Facebook Page located on Facebook at "Hollyman Family". Post your questions and perhaps one of the dozens Holyman cousins on the list will have an answer. For more information contact Tina Peddie at desabla1@yahoo.com, the list and Facebook manager for Hollyman (and all our various spellings!).

Since early 2010, I have been publishing research and stories on the broad spectrum of Holliman (Holyman) family history at http://hollimanfamilyhistory.blogspot.com/ . For stories on my more immediate family since the early 20th Century, I have been posting articles since early 2011 at http://ulyssholliman.blogspot.com/ .

Let's save the past for the future! If you have photographs, letters, memorabilia or research you wish to share, please contact me directly at glennhistory@gmail.com. Several of us have an on-going program of scanning and preserving Holyman and related family records. Write please and tell us of your items. Thanks to the Internet, we are able to scan, upload to the web (with your permission) and return the materials to you.

Announcing also a "Seminar and Site" gathering October 18 and 19, 2013 in Fayette, Alabama for Hollimans and associated families whose ancestors are from that area. Space at the Rose House Inn is limited for the occasion due to a football weekend. For information, contact me at the above email.  - GNH