Honoring Sacrifices, Dreams you nurtured, and the Love you bestowed upon our Lineage.

Honoring Those Who Came Before Us, Isaac and Ann Grey Holleman

by Susan White, Holleman Genealogists and Historian

Editor's note, this is the climax of the Isaac and Ann Grey Holleman story which first surfaced in this blog when your editor shared lunch with Sandi Royal in 2013.  Descendants of  Josiah Holleman of Isle of Wight County, Virgina, both African-American and European American, have been jointly researching this American story for over a decade.  On Saturday, March 1, 2025, Charles Holleman descendants visited the site of Isaac's farm, one mile south of the town of Windsor, Virginia, off Route 608. Susan White explains how the story unfolded. - Glenn N. Holliman

 Family

Our white Holleman ancestors in Isle of Wight, Virginia, enslaved people.  We don’t know if that practice started with Christopher Holleman (Holliman, Hollyman), our first immigrant, but it could have.  Christopher grew tobacco, a labor- intensive crop, and must have needed helpers for his harvest.  My fifth great grandfather, Josiah Holleman, (1771-1848) enslaved at least eleven Black men, women, and children during his lifetime, including Isaac Holleman (1818-abt 1898), the main subject of my family genealogical research for years.  He fathered Isaac, and at least one other Black man, James (1825-unk) with an enslaved black woman. Isaac’s story was shared in public at a presentation sponsored by the Isle of Wight Historical Societyleast on June 22, 2024 at the Georgie Tyler Middle School, Windsor, Virginia. 

Isaac’s descendants, have been enlarging this story that continues to broaden.  Glenn Holliman first mentioned Isaac in his 27 June 2013 blog post where he spoke of Sandi Royal’s research and retelling of family lore, that Isaac “ran off with Ann Gray, a white woman,” whose family was against the relationship.  Sandi spoke of a picture of a “white woman” that hung in her family’s house for years.  I learned of this story in 2016, from Glenn, at a Smithfield, Virginia Holleman family reunion.

 Glenn N. Holliman and Susan White at a 2016 Isle of Wight conference. 

At that time, I had just begun to research my own connection with Josiah Holleman, who was my fifth great grandfather.  One of his sons, William Henry Holleman (1795-1834), was my own Holleman ancestor, and he was an enslaver, as well.  Identifying the relationships between my Holleman enslavers and enslaved people around Isle of Wight county in the eighteenth and nineteenth centuries has been and continues to be difficult. We discovered some of the truth of Ann Gray, however, and where she came from, most likely Nansemond County, VA.  Sandi Royal, my daughter Lea Marshall, my brother, Eddie Gallier and I have used the tools of DNA, paper records, National Archives aerial photography, and sometimes pure dumb luck to dig into this story.                

Isaac fathered children first with Malinda Pretlow, a free black woman, and then with his wife, Ann Gray.  Descendants from both unions have connected over the past few years to learn more about their roots.

Sandra Royal 

 

                                                               Nonnie L. Holliman
                   

 Kenya Allmond

 

The Family Farm in Windsor                       

 After their escape from enslavement during the Civil War, Isaac and Ann Holleman bought a 50 acre farm in 1871, about a mile south of the town of Windsor, Virginia.  This was no small feat.  They owned their farm, did not sharecrop, and the farm stayed in the family until 1963, when  James Trueheart Holliman, a grandson of Isaac, sold the farm to W. T. Joyner.  It was sold one more time before the Norfolk and Western Railroad bought it in the early 1990’s.   

The 1880 agricultural schedule reveals his livestock and crops and the effort Isaac was expending to provide for his family:

1 horse, 1 mule, 1 working ox, 1milch cow and calf, 9 swine and 13 poultry

100 bushels of corn, 20 bushels of sweet potatoes, 50 bushels of apples, 50 bushels of peaches.

He cut 60 cords of wood the year previous.

About 2023, in one of those lovely serendipities of genealogical research, Jim Henderson of the Isle of Wight County Historical Society discovered an old file on his computer that another Society member must have shared with him at some point along the way. The file was a part of an environmental impact study undertaken by William and Mary Archaeological Department for the Norfolk and Western railroad (now Norfolk Southern Railway) as it was buying the farm from the Joyner family.  Another stroke of good fortune was that the archaeologists met Reverend Arthur Holleman, a great-grandson of Isaac, who knew the farm when it was in the family, and enlisted his help to identify what they were finding in their labors. 

 To read the report is to marvel at what Isaac Holleman accomplished.  Unfortunately, as time passed, the farm became lost to the descendants who lived in the area.  No one living knew exactly where it was.  On two different occasions, a group of Hollemans attempted to find it using the maps in the Norfolk and Western study, but we were not very good at reading the many-times-copied maps.  The third try was successful, and luck was with us again. 

In November, 2023, as the county farmers were harvesting their cotton crops, we discovered the dirt road off of Route 608 in Isle of Wight, and the chain across it was down.  We were able to drive down the rutted road and found the farm.  About 8 bales of cotton were stored at the edge of the field, waiting to be taken to the cotton gin.  Jim and I got out of the car and began to walk the field of cotton stubble.  It was a beautiful day and we were very excited.  Jim wondered who farmed the field?  Maybe we could find out?  

It was late in the day, but Jim thought we should drive over to the cotton gin facility, to see what we could find out.  Luck prevailed again.  The owner of the gin gave us a name of possible farmer, and I called him.  He was not the one in this case, but he gave us the name of who he thought might be our man, and Success!  Mike Griffin was the farmer who still leases this land from Norfolk Southern Railway.  He has been farming the field since about 1995.  

                                                     Susan White and Lea Marshall

In January, 2024, my daughter Lea and her husband, Will Kerner, visited the farm, this time hoping to obtain more pictures.  Will has a drone camera, and he was able that day to take aerial pictures.  It was a cold, dreary day, and this time the chain at the entrance to the dirt road was in place and locked.  We had to walk the long, muddy road to come to the field, rather than driving.

Courtesy of William Kerner. Windsor is the white border upper right. The highway separates water (left) from the brush covered terrain, center on the far right.

Jim Henderson has been our best cheerleader in uncovering Isaac Holleman’s story.  He has encountered a group of us for several years in our pursuit of Isaac’s story.  He invited us to present what we were learning to the Isle of Wight Historical Society.  Our group, in particular, Sandi Royal and Nonnie Holliman, who are both Isaac descendants, agreed.  My daughter, Lea, my brother, Eddie Gallier, and Glenn Holliman were also eager to share the story.                                                                                                                 

 Eddie (pictured) is an avid modeler, particularly in constructing model train layouts.  The man has skills.  I asked if he would help us to create a model of Isaac’s farm.  He agreed, and In 2023, in order to learn more about the farm, he contacted the U. S.  National Archives to inquire about U. S. Department of Agriculture aerial mapping.  Thanks to the generosity of several family members, Eddie obtained the 1930’s-1950’s aerial photos of the Holleman farm from the Archives. 

1938 aerial view of farm with structures in the middle of the picture.

He also had the Norfolk and Western study to refer to. He created the farm layout in HO gauge; the house, barn, outbuildings, well, smokehouse, the family graveyard and the orchard.  He photographed them all, so they could be included in our presentation.

                                                        Model of farm by Eddie Gallier

 On June 22, 2024, as part of Isle of Wight Historical Society’s Juneteenth observation, we told “The Extraordinary Life of Isaac H. Holleman” at Georgie Tyler Middle School.  About eighty people attended, many of them descendants of Isaac, Malinda, and Ann. 

Season and Weather

Our research group has visited various Holleman related sites in Isle of Wight over the past 3-4 years.  One day was in March, bitter cold and snowy. Then a couple of summer days where I got chigger bites in the Tyler Cemetery. Then another beautiful late fall day, and a dreary, depressing January day.  Doing so, however, reveals another layer in Isaac’s life.  He encountered all kinds of these days during his life in Isle of Wight.  We were fortunate to encounter them, also.

Now we know where the farm is and can visit, but because the Holleman farm is an actively cultivated field, we visit with full knowledge of season and weather and respect the farmer's work. We can visit from early December until mid-March.  We trudge through mud and crop stubble, as Isaac and his family did.  This spring we rescheduled twice a trip due to snow. 

This past March we finally made it was a warm, early spring day, occasionally windy, but not uncomfortable.  As we crossed the swampy area at the entrance of the field, we heard frogs.  We heard the headwaters of Ely Swamp gurgle.  You could hear the wind.  Below muddy fields and swampy bogs.                                                 

Prior to our trip, my brother had helped me load coordinates into my phone Google map, of the family graveyard, the  house, barn, and the orchard.                               

 

 We made our way across the field, hammered stakes into those sites. We stopped at the graveyard site and prayed a prayer that Nonnie Holliman had written for us.

 

Right to left: Nashawn Holliman, Alexander Holliman, Kenya Allmond, friend of Kenya, Sandi Royal

A Prayer of Remembrance for Ancestors at the Holliman Farm, March 2025

Dear God and Ancestors,

We gather in reverence and gratitude, remembering your spirit, your wisdom, and your strength. Your journey through life laid the foundation upon which we stand, and your legacy continues to guide us with every step we take. We honor your sacrifices, the dreams you nurtured, and the love you bestowed upon our lineage. Your stories, though sometimes untold, are woven into the fabric of our existence, and we cherish the lessons they impart. May we always strive to live in a way that makes you proud, carrying forward your virtues and values. As we reflect on your lives, we seek your guidance and protection. Help us to face our challenges with the same courage you displayed, and to celebrate our triumphs with the same joy you felt. May we be ever mindful of the paths you forged, and may our actions today honor your memory. In moments of doubt, may we feel your presence, and in times of celebration, may we sense your joy. Your spirits dwell within us, a constant reminder of the enduring bond we share. We are eternally grateful for the roots you have planted and the legacy you have left behind.

With deep respect and love, we remember you. Amen.

By Reverend/Superintendent Nonnie L. Holliman, Great Grandson of Isaac and Ann

 That day we could be where Isaac and his family lived and died.  It was a very good day.

Where did James Grantson Holliman Live? (1750-1836)

 by Glenn N. Holliman and Sally Campbell

Background

James Grantson Holliman’s great-grandfather, Christopher Hollyman (1618-1691), gave up his home in Bedfordshire, England, and sailed the dangerous Atlantic with his sister, Judith.  They arrived in Jamestown, Virginia in 1650.  Judith married and disappeared from history.  Chris farmed, married, and, by his death, had accumulated over 1,000 acres in Isle of Wight County.

Christopher divided his land among his four sons.  One of them, Richard, chose to stay in the area and expanded his share of the family's legacy by acquiring land in Surry County.  His son, Samuel Holliman (1707-1789), inherited his grandfather’s adventurous spirit and relocated to Edgemore County, North Carolina.  Years later, possibly due to the depletion of his land from years of tobacco farming, Samuel moved again, this time to Johnston County, North Carolina. 

This map was passed along to this writer by the late Rhodes Holliman, Ph.D. It shows in yellow and purple markings where James Grantson Holliman performed his militia service during the American Revolution when he lived in Johnston County, North Carolina. For a copy of his pension application, one may visit Hollyman Tree (Holyman Heritage Group) at Ancestry.com or www.bholliman.com, a virtual archive of associated family materials.

Either in Edgemore or Johnston County, James Gantson Holliman came into this world in 1750 and died in 1836. After service in the North Carolina Militia during the American Revolution, he followed in his ancestors' footsteps and moved to newer, richer farmland. 

James purchased property in what is now Union County, North Carolina, and Lancaster County, South Carolina. There, he prospered. His sons Charles, Warren, and Cornelius married, but like their father, other ancestors and tens of thousands of young Americans, continued the westward movement. Their destination was Fayette County, Alabama. Warren would move on to Arkansas after a few years in Alabama.

Cornelius received a free land grant for his service in the War of 1812.  Perhaps the other brothers migrated in order to establish larger, more productive farms.  Sally reminds us that in order to move family, stock, tools and supplies in a wagon train, migrants had to have a certain amount of cash or trade goods. One did not start a new farm and house penniless.  The people left behind were either financially established, impoverished, or elderly like James Grantson Holliman. His daughters did not move to Alabama.  They stayed in the Carolinas most probably to care for their father in his final months.

New Research

Sally Campbell, a descendant of James Grantson Holliman, has searched land records and traveled the countryside of Lancaster, SC and Union, NC counties to discover precisely where he farmed and raised his family. James owned properties on both sides of the state borders, which confused his descendants as to whether they were South or North Carolinians. 

He took an oath in Anson County (now Union County) for his Revolutionary War service.  In his 80s, it appears that James had a disability, and he went to Monroe (Courthouse), NC, rather than Lancaster (Courthouse), SC, because there were fewer creeks to cross by cart and horse. Does this research clarify the location of his legal residence?  Perhaps his descendants can claim citizenship from either state!

 Sally’s research reveals:

 1. James owned property along Lynches Creek, the boundary between Lancaster and Chesterfield, South Carolina counties.  Anson County, North Carolina, was divided later, and James' property was in what is now Union County.

 2. James also owned land in South Carolina adjacent to Paul Plyler at the fork of Wild Cat Creek, on the south side of Great Lynches Creek, and on the south side of Pole Cat Creek.

 3.  Paul Plyler, a major property owner, had possession of South Carolina land on both sides of Otter Creek and Little Otter, a branch of Lynches Creek, and Wild Cat Creek.

 This map prepared by Sally shows Monroe, NC where James took his Revolutionary War service oath.  Underlined in red in North Carolina is the Pole Cat Creek property area.  In South Carolina underlined in red is Otter Creek. 

This is a close up of the map.  Tradesville, nearer than Monroe, NC, to Holliman property, probably was the village of choice to purchase supplies.  Pole Cat and Otter Creeks are underlined west of the Lancaster and Chesterfield County lines—the county line defined by Lynches Creek.  

Building on the thoroughness of Sally’s research, I pulled up a map that the late Walter Holliman did in the early 1990s before the internet era. Walt, whose family donated his research to this writer, reinforces Sally’s work. He, too, identified South Carolina creek branches where Hollimans and Plylers lived. At the top of Walt’s map, he also shows there were Holliman and Blakeney properties on the North Carolina side.

All three of these families, or at least some of their offspring, moved to Fayette County, Alabama, where some of descendants live to this day.  Cornelius Holliman received his Alabama land as a grant from War of 1812 service.

I want to thank Sally for reaching out to provide this information, her interpretations and catching typos. Not only was James Grantson my fourth GGF, but his neighbor Paul Plyler is also my fourth GGF because his daughter, Elizabeth, married Cornelius Holliman, my third GGF. This story affirms what historians have written: neighbors married neighbors, and neighbors often migrated in families in America’s westward movement. It appears that the Carolina neighborhood caught ‘Alabama Fever’.

Sally Campbell is a descendant of both Cornelius Holliman and Charles Holliman, double-descended from James Grantson Holliman.  Below is her story. - GNH

My parents were from Texas and stationed in Washinton DC during WW2, and that is where I and my twin sister were born.  After WWII, they moved to a suburb of Philadelphia PA, where I grew up.  I graduated from Simmons College in Boston, and married and moved to NY state for 10 years.  Then my husband and I moved  to Charlotte NC, with our three children.  I worked in Computer Services for UNC-Charlotte for about  fifteen years, then my husband and I bought a cruising sailboat which we sailed to the Bahamas and back for 3 or 4 winter months almost every year for 20 years.  

I have always been interested in family history then was started in researching names, dates when I interviewed my paternal grandmother about her 8 siblings. I wish I had interviewed all my grandparents.  I knew my maternal grandfather Elijah J. Holliman was born in Fayette, Fayette County,  north western Alabama.  I discovered Newells' History of Fayette County, which mentioned that Cornelius and his wife Elizabeth Plyler were from South Carolina. I found 'The Plyler Genealogy'  by Monroe, NC.author Herman Starnes.  With the Internet it was easy to communicate with the late Maxine Wright of Arkansas. - Sally Campbell

The sources for this article are based on land abstracts from the book 'Some South Carolina County Records Vol. 1 by Brent Holcomb, printed in 1976, pages 143 through 195, and 'Lancaster County South Carolina, Union County North Carolina metric Topographic Map' by the US Geological Survey printed in 1986.

 

Jeff, Richard and Don Holiman, Part 2

In my last blog, I focused on the fascinating life of my distant cousin, Richard Holiman (b.1946), a pioneer American businessman in an emerging China the 1980s. Richard's own father, Don (1916 -1985, born in Benton, Arkansas) led an even more iconic life of travel and achievement which is high lighted below.  My thanks to Richard and his son Jeff (b.1971) for sharing details on their ancestor. - Grace A. Holliman

“My father was prone to spontaneous wandering….” – Richard Holiman on his father, The Rev. Don Holiman

When he was a teenager, Don Holiman rode the rails as a more-than-less vagabond, but he was a vagabond on a mission. In 1932 the L.E. Waterman Company, one of the leading fountain pens manufacturers of the day, launched an autograph collecting competition. The Waterman Company supplied young people with a special book and gave them six months to collect as many autographs of famous people as possible. When the six months were up, the participants had to mail their book back to the company in hopes of winning one of the 333 prizes with the grand prize being $1,000. Don Holiman was in the top 33 and won ten dollars!  

The clipping below articulates his venture.

By age 27, Don was living in San Antonio, Texas and was concerned about the number of homeless and abandoned boys he saw sleeping in Travis Park. Don knew that the local police placed these boys in detention to give them shelter despite their having committed no crime. To help these young men, Don founded Boysville. Boysville started at a large home on Avenue A and eventually moved to a pastoral area where the residents could learn skills such as tending crops and raising animals.  The home continues to this day in Converse, Texas!

Above: a story on Don's home for boys in Texas.

Below: 1943, Don, wife Sibyl, with the legendary Father Flannigan at Boys' Town in Nebraska.

Don eventually parted with Boysville and hit the road again as a traveling salesman. “My father was prone to spontaneous wandering,” recalled Richard with a smile.“ He went from San Antonio to Oakland to Atlanta to Dallas and would send letters back to my mother. More often than not, those letters contained his poetry instead of money.”

Left: Sibyl, Richard and Don, ca 1958 

Don was also a hellfire and brimstone Baptist preacher who, for a time, had a church near a military airfield. One Sunday morning the military was practicing a raid at the same time Don was preaching. As the story goes, the moment Don slammed his hand down on the pulpit, a bomb went off. Richard laughed as he spoke and said, “A lot of people were saved that day!”

Below: Don Holiman behind the pulpit. 

Jeff was ten when his grandfather passed in 1981, but he still has vivid memories of Don. “He made me a slingshot and taught me about toys and games of his era. He also woke me up at three in the morning to go fishing. I remember thinking, ‘Who in the world goes fishing at three in the morning?’” 

Jeff recalled going down to the train tracks with his father and grandfather and putting pennies on the tracks. “It was like a treasure hunt,” Jeff said, “trying to find the pennies after they had been flattened by the train and shot off the track.”

Above, Don in later years looks on a picture of one of the original Boysville buildings in Texas.

As our interview wrapped up, Jeff added that his grandfather was a mesmerizing storyteller. “He was an adventurer.” Richard added, “My father would say, ‘Trust in the Lord and He will provide.'

After saying “goodbye” to Richard and Jeff, I felt gratitude and admiration - grateful that these two distant relatives were comfortable enough to share their stories with a stranger, and admiration of their connection to each other and their passion for not only researching the past but asking questions in an attempt to understand humanity.  - Grace A. Holliman

For information on Hollimans (various spellings) and their many associated families, visit www.bholliman.com, a virtual archive of over 3,500 folders on Hollyman genealogy, their history since 1347 and many maternal families.

Jeff, Richard and Don Holiman, Part 1

 Last spring Jeanette Holiman Stewart, my wife Barbara and I had the joy of visiting the multigenerational family of Richard Holiman in Florida.  It was really a genealogical fest as we compared notes on the Hollyman paternal line from England to Virginia in 1650 and the diaspora throughout America.  Along the generations, the name has been spelled several ways. The Holiman spelling largely emerged when the Warren Holliman family in the late 1830s moved from the Carolinas first to Alabama and then to Arkansas, dropping an ‘l’ along the way.

This blog also introduces a new genealogist of our shared lineages, my daughter Grace A. Holliman, pictured right, an English major from Virginia Tech gifted with story writing skills. As with me, she appreciates how our families have lived and moved through history.  In this article, she interviews our distant cousins. – Glenn N. Holliman

The Richard S. Holiman Family Story, Part 1 by Grace A. Holliman

“He wasn’t afraid to go off the beaten path….” – Jeff Holiman on his father, Richard Holiman

As I began my virtual interview with Jeff Holiman and his father, Richard, the first thing I noticed was the genuine connection between the two generations. Jeff (b.1971) and Richard (b. 1946), were at ease sitting next to each other at a table in Jeff’s home in Clearwater, Florida. As we began our introductions I had the pleasure of meeting Gina, Jeff’s wife, who has been an important contributor to Jeff’s Holiman family research. Jeff also credited his aunt, Lynda Holiman Jones, with sparking his interest in genealogy over twenty-five years ago.

Left to right, Richard S. Holiman, Kimberly D. and Jeff Holiman, children of Richard and Ryan B. and Jayden S. Holiman, children of Jeff.

“I was in college when my parents lived in Hong Kong,” Jeff, now a mortgage banker,  said. “While most people went home for spring break and Christmas, my sister and I flew to China. It was the late 1980’s and China was changing, opening to the western world by making and selling products that Americans wanted to buy."

Richard was part of this process. He began as a buyer for Eckerd Drugs and had a firsthand look at the role that factories played in small Chinese communities. “Entire villages were employed by these factories,” Richard said. “Children would come by after school in search of work. Often there were jobs they could do, like placing stickers on a package to keep it closed.” Richard reflected and continued, “These were poor people trying to make a living. All they wanted to do was work to get ahead and take care of the older generation.”

Gina (left) wife of Jeff with Jeanette Holiman Stewart, author of the Ancestry.com Hollyman Family site. They stand in front of a genealogical map produced by the Richard Holiman families. 

Jeff recalled a trip to Beijing’s Tiananmen Square. “On one corner there was a solider with a machine gun and on another corner, a Kentucky Fried Chicken. The KFC had a long line wrapped around the building. Because we were Westerners, our guide took us to the front of the line where we were served quickly. It was uncomfortable. As we ate, I watched our guide consume every morsel of chicken off the bone. I compared his bare chicken bones to our pile of bones with bits of meat and gristle still on them that we were going to throw away.”

 Jeff remembered how Richard would take him down streets where guides didn’t take tourists. “Dad would take us to see everything. We would walk around the block and see men squatting in alleys playing Mahjonng or Go. He wasn’t afraid to go off the beaten path to show us what life was really like.” Jeff paused and added, “I have deep respect for the vast, rich history of the Asian culture and appreciation for the life my parents gave me in the U.S.”

Richard Holiman in the 1980s in Tiananmen Square, Beijing, China

Richard, the well dressed western businessman in China at a factory four decades ago.

As this part of our conversation ended, Richard quietly added, “People in Asian cultures are amazing.”  With that, the three of us paused and I realized how profound Richard’s career had been for him and his family. As our conversation continued I began to understand where Richard, the youngest of three sons of a Baptist preacher, inherited his proclivity for exploration and learning and caring for others.  - Grace A. Holliman

Note: the story will be continued in the next blog.  To learn more about Hollyman and associated families, please go to the comprehensive archive of over 3,500 items at www.bholliman.com.  This site also contains information on the parental Hollyman lines (various spellings) as far back as the 1300s in England.

 

 

 

 

 

Reflections Concerning Isaac Holleman, Part 3

by Glenn N. Holliman

This continues the saga of Isaac Holleman, born in 1818 into slavery at the Josiah Holleman plantation in Mill Swamp, Isle of Wight County, Virginia.  This time line prepared by Susan G. White, direct descendant of Josiah and major historian of the life and times of Isaac Holleman and his wives.  The words in italics are mine, reflecting on the confusion of the Civil War era.- GNH

A picket fence stands before the current house at Stawberry Plains, the original Urquhart plantation in Isle of Wight County, Virginia.

1848    Josiah Holleman died.  Isaac Holleman sold back into slavery for $355 by executor Isaac Cofer, to Richard A. Urquhart, a wealthy slave owner who lived at Strawberry Plains, about 6 miles from Josiah’s home.

            Malinda Pretlow’s father, Moses Pretlow, is on a list of Josiah Holleman’s debts, in Josiah’s handwriting, of being owed $2.76.  Malinda was the mother of Isaac's first three children.

           Moses and Malinda were free; Isaac was enslaved.  The nuances of Virginia society in the antebellum South are fascinating and puncture the 'Gone with the Wind' concept of a static society.  Free African-Americans lived side by side with enslaved persons and European-Americans, some slave owners, others yeoman farmers working the land with family members or hired hands.  

1850       One black male slave, age 30, Richard Urquhart’s slave schedule (believed to Isaac)

1852       Birth of Isaac’s son Robert Holleman, to mother Malinda Pretlow

1854       Birth of daughter Ada, to mother Malinda Pretlow

1858       Birth of son Moses to mother Malinda Pretlow

1860       Richard Urquhart dead.  His widow continued to own slaves.  Census schedule shows 133 slaves, of whom 2 males are ages 45 and 40.  Isaac would be 42 by then.  He would know the domestic slave quarters still standing on Strawberry Plains Farm.

            Census records reveal that Stawberry Plains was the second largest community of enslaved persons in Isle of Wight County prior to the Civil War.  Enslaved plantations of this magnitude were the exception in American slavery.  One can scarcely imagine the sub-cultures within a population of this size.

                Free Negro Malinda Pretlow is listed on the 1860 census, shown a few dwellings down from R. Pretlow.  She lived on Proctor’s Bridge Road, in Southampton County, west of Proctor’s Bridge.

           During the Civil War, Fortress Monroe located on the north side of the James River, some miles east of Isle of Wight County, became a haven for 'contrabands', former enslaved persons who escaped to the freedom of the Union Army.  One of these persons was Isaac.  There is a mystery here because his three children of Malinda Pretlow, all born free, either went with him or joined him at Fortress Monroe.  At some point in the Civil War, Malinda, who lived long after the war, and Isaac separated.  Isaac must have met Ann Gray during the confusion of this turbulent period and made her his second wife while at Fortress Monroe.

1866       Freedman’s Bureau records show Isaac petitioning for money October 1866 to return home to Nansemond County, along with Ann Gray Holleman, Robert, Ada, and Moses Holleman, to “escape destitution.”  He also petitions for money due his son Robert for work son did for Mrs. Binford, who lived just west of Proctor’s Bridge in Southampton County.

            Nonnie Holliman and Sandi Royal, descendents of Isaac and Ann Gray at the Stawberry Plains farm March 2022 where their ancestor worked and from which he escaped to freedom during the Civil War.                                                               

 1867       Birth of daughter Luzerne.  Mother is Ann (Gray) Holleman

 1870       Malinda Pretlow listed on Southampton County 1870 census.

1871       January 1.  Isaac and Ann buy farm from Nathaniel P. Phillips, made payment of $50.  Farm previously owned by Cary Eley. This farm located a few miles south of Windsor.

1873       November 11.  Isaac pays remainder of farm money, 194.01, to Phillips’ executor, John R. Kilby, and receives deed to the 50-acre farm.

1876       Birth of son Nonnie

1878       Birth of son Jeremiah

1879       Birth of son Joshua

1880       Isaac, Ann, and children on census

Census farm schedule identified Isaac’s farm and its assets

1881       Birth of son Joseph, who died in infancy, about age 1 yr

1883       Birth of son Joshua

1885       Birth of son John Henry, Sr.

1888       Birth of daughter Joanna

1889       Dec. 23 document of Isaac and Ann paying $50 to trustee George T. Atkins, presumably for a debt to neighbor Richard F. Eley.  Debt was satisfied.

1890       U. S.  census burned.  No records.

1897       Last time Isaac paid taxes on farm.

1898       Farm then in name of “Holleman, Isaac, estate”.

1900       Wife Ann on census, with children living with her.  She owned her own home/farm. The date of her death is unknown.  Both Isaac and Ann are buried on the farm, now in unmarked graves.  The property has been part of the Norfolk Southern Railroad since the 1950s.

So here we have the incrediable, tragic, heroic story of Isaac Holleman who born a slave, freed, taken back into bondage, escaped to freedom, became a land owner during Reconstruction, raised children from two wives and whose descendents today are scattered across the USA.   

Abraham Lincoln in his Gettysburg Address spoke of a 'new birth of freedom' in America.  Isaac perservered in conditions and circumstances unimaginable today.  He bears the name Holleman.  And all, descendants and those of the same surname, salute him for his courage and steadfastness in adversity.  - GNH

Reflections Concerning Isaac Holleman, Part 2

 by Glenn N. Holliman

This reflection continues our exploration into the life and times of Isaac and Ann Gray Holleman, a biracial couple who challenged the strict norms and laws of post Civil War Virginia.  In my previous article I acknowledged and do so again the serious research by Susan G. White, a descendant of Josiah Holleman (1771-1848), who has discovered new facts about this amazing story.  

Susan has prepared a valuable timeline of the events in the life of Isaac.  With this information, I have integrated photographs from a visit of Isaac descendants and several of us in the lineage of Christopher Hollyman (1618-1691), the ancestor of most Hollimans (various spellings) in the United States.  

The parents of Isaac are not known.  At least one Federal census records him as of a mixed race.  Was his mother an African American held in bondage and his father, a man, perhaps a slave owner?  DNA tests have not yet provided us that information.  As early as the 1680s, Virginia law forbade sexual relations between those enslaved and White persons.  As historical and DNA records show, numerous White males through the generations ignored this restriction.

Timeline for Isaac Henry Holleman (1818-1897 ca) by Susan G. White, Hollyman Family Historian

1810       Josiah Holleman owned 9 enslaved people

1811       He bought 2 more, woman Harty and girl Lavinia

1818      Birthdate of Isaac Henry Holleman, according to Freedman’s Bureau record

1820       Josiah Holleman owned 15 enslaved persons, including 9 males

Isaac was born on the original property purchased by Christopher Hollyman in 1684, land that remains in the Holleman family to this day.  The current owner, Billy Joe Holleman, opened wide this ancestral property to a large gathering of Hollemans in 2016 and again he graciously welcomed our group in March 2022.  Josiah Holleman was a 4th great grandson of Christopher's.  One of Josiah's sons, Joel, served as a U.S. Congressman.

Left to right, Tammy Hunt, Susan White, Billy Joe Holleman and Isle of Wight historian, Jim Henderson, on the Holleman farm near the Mill Swamp Baptist Church in IOW county.  This stop one of several on March 12, 2022.  

 

1823      Malinda Pretlow born, Free Person of Color, daughter of Free Black parents             

1830      Josiah owned 14 enslaved persons, including 8 males, 3 ages 10-23

The Holleman House constructed in the 1830s by Josiah Holleman on original land of Christopher Hollyman (1618-1691). It is not unrealistic to imagine young Isaac Holleman had a hand in constructing this federal period structure.     

 1836       Isaac, age 18, emancipated, via Josiah’s petition to the court.  

1840       Josiah’s census listing shows 1 male Free Person of Color, age 10-23, 1 female Free Person of Color under 10, and 8 enslaved beings.   

1848      Josiah died with many debts.  Isaac sold back into slavery for $355 by executor Isaac Cofer, to    Richard A. Urquhart, a very wealthy plantation owner who lived at Strawberry Plains,  8 miles from Josiah’s home.  Malinda’s father, Moses Pretlow, is on list of Josiah   Holleman’s  debts, in Josiah’s handwriting, of being owed $2.76. 

            Fear and Stress in Pre-Civil War Society

            A decade before Josiah's death, the 1831 Nat Turner slave rebellion occurred in nearby Southampton County resulting in the death of any many as 55 persons.  This incident terrorized the White south as it fulfilled the greatest fear of slave owners!  Night patrols of anxious local authorities road at night insured no enslaved persons stirred from their homes without permission.

            A generation prior to the Civil War, the tobacco economy of Virginia suffered as the soil worked in earlier generations was exhausted of nutrients.  Josiah's indebtedness at death is a vivid example of the increasing economic challenges of Virginia enslavement plantations to be profitable.  Nearby Richmond had become a slave trading mecca where tens of thousands of human beings were sold at auction.  

            In many. many cases persons were separated from their families and homes and literally in chains marched hundreds of miles to the newer, soil rich plantations in Alabama and Mississippi. This nefarious system shattered the unity of African-America families, their security and fragile culture.  The ramifications of this evil institution ricochet through American society to this day.        

          Questions and Thoughts to be Considered

                                                   Nonnie Holliman and Sandi Royal

            On our way back to Richmond, Susan White, Sandi Royal, Nonnie Holliman and I speculated  on several issues in this story.  As I wrote years ago (click on name of Isaac Holleman in left column), pre-Civil War IOW of Wight County was an uneasy, largely agrarian, society of slave plantations, yeoman White farmers with no persons held in bondage and numerous Free Persons of Color. 

         1. Why, when Isaac received emancipation in 1836, he was again enslaved by 1848 and sold to pay Josiah's estate debts?  Had Isaac, who as a Free Person of Color with very limited civil rights after legal emancipation, violated a law, a slave code of the time, and as punishment forced back into to bondage?  There are cases of this happening.

            2. We noted Josiah owed money at his death to Moses Pretlow, a free person and father of Malinda, Isaac's first wife.  There then was some integrity in a system that recognized contract law even with free African-Americans who navigated a precarious legal and societal existence.

            3. Moses was the father of Malinda Pretlow, who 'jumped the broomstick' with Isaac and bore him at least three children, perhaps two others.  'Jumping the brook stick' literally was the folk custom of marriage of enslave persons prior to establishing legal rights after the Civil War.   

            Left to right at the Pretlow farm near where Malinda Pretlow lived are Doris Knox and Tammy Hunt, direct descendants from Isaac and his first wife Malinda.  Far right is Nonnie Holliman, descended from Isaac and Ann Gray Holleman.  The empty house in the background was constructed ca 1870 during the Reconstruction Period.

               Malinda lived approximately a mile (as the crow flies) from the Holleman plantation eventually living separately from her father.   This couple had three children before the Civil War which evidently led to their separation. 

At the Pretlow farm, current owners Mary Leatherwood and Adrian West shared an aerial photograph of the property as it looked in the early 20th Century

How did the couple sustain a relationship that resulted in children, separated as they were by some distance and legal status?  At age 30, Isaac had to move to Strawberry Plains, a farming community of over 100 enslaved African-Americans, miles away from Malinda.  Perhaps this doomed the marriage?

Next article more information and yet more questions on this story of 19th Century America, an America that had yet to live into its creed of liberty and justice for all. Only a Civil war would give Isaac and millions of others 'a new birth of freedom.'-GNH