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