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