The Saga of Isaac and Ann Gray Holleman of Isle of Wight, Part 1

by Susan Gallier White

Susan G. White of Virginia is one of the more scholarly writers of  Holleman/Holliman family history of our generation. What follows is the first article of several of the latest information into the fascinating story of an unlikely 19th Century couple, Isaac and Ann Gray Holleman of Isle of Wight County, Virginia. 

In her research, Susan had consultations with Nonnie Holliman and Sandi Royal, who descend from Isaac and Ann, and Troy Jenkins who descends from Isaac's first wife, Malinda Pretlow.  At this site, earlier articles on Isaac and Ann Holleman were published in September 2012 and May/June 2013 by yours truly.  Mrs. White's work greatly enlarges our knowledge of this American story.

Susan wrote August 2016 at this site of her ‘ahead of their time’ Holleman and Faison ancestral grandmothers.  Susan also attended the Spring 2016 Holliman/Holleman in Isle of Wight and later the Spring 2019 Hollyman ancestral exploration in England. - Glenn N. Holliman

 

Above, Susan and I converse at our opening session of the May 2019 Hollyman gathering in Moreton in Marsh, England.  Back right is cousin Lindsay Holliman, descended as were all Hollimans present, from 15th Century Cuddington, Buckinghamshire, England.  Lindsay lives in Edenborough, Scotland.

Isaac Holleman, a Black man, owned by Josiah Holleman, was born into slavery in 1818 at Mill Swamp district, Isle of Wight County, Virginia.  Emancipated in 1836, he was enslaved again in 1848 to Richard Urquehart, to help pay Josiah Holleman’s estate debts. 

During the Civil War, he fled with his family, including his White wife Ann Gray to Fortress Monroe, Virginia when it was commanded by Union General Benjamin Butler.  Butler, a career Massachusetts politician, regarded Black runaway slaves as contraband, and refused to return them to their owners.  Contrabands by the tens of thousands experienced freedom wherever Union Armies marched.  

One such family was named Holleman.

The 1830s Holleman house is on the original land purchased in 1684 at Mill Swamp, Isle of Wight County, Virginia by Christopher Hollyman, (1618-1691) founder of most of the Hollimans (various spellings) in the United States. This picture taken in 2016 as Hollemans/Hollimans/etc. gathered from all over the country.  The home is owned by Billy Joe Holleman.

After the war, Isaac requested and was granted transportation for himself and his family to Nansemond County, Virginia, in October 1865. He settled in Isle of Wight County, bought a farm of 35 acres, where he lived with his second wife, Ann Gray.  Isaac’s date of death is unknown. His story is only recently discovered by White Holleman descendants but has been in the oral history of his Black family handed down by generations.

 Freed persons with Union Soldiers at Fortress Monroe during the Civil War.

The distance between Mill Swamp Road, Isle of Wight, Virginia, and Fortress Monroe, Virginia is about 36 miles.  The elapse of time between 1619, when slaves were first brought to Jamestown, Virginia and 1818, when slave Isaac Holleman was born, is almost 200 years.

Holleman ancestors were part of that distance and time span beginning in May 1650, when Christopher Hollyman came to Isle of Wight County, Virginia from Bedfordshire, England.  

Thirty-four years later, at age 66, Christopher patented 1020 acres of land in the Mill Swamp area.  The son of an inn keeper and shoemaker, Mr. Holleman undoubtedly succeeded beyond his wildest dreams.  He died at age 73 and divided his plantation which bordered Surrey County among his four sons. Tobacco barns were recorded in his will but no slaves. 

The slave economy grew slowly in the 1600s, but exports of Africans in bondage exploded in 18^th Century Virginia.  It was in the 1700s when most likely the ancestors of Isaac arrived in Virginia.  This tragic plantation economy ironically supported many founders of the new United States – for example, Patrick Henry, Thomas Jefferson, George Washington, James Madison and James Monroe.

Fortress Monroe, Hampton Roads, Virginia in the 19th Century where Confederate President Jefferson Davis was imprisoned in chains after the Civil War.  The Isaac Hollemans at the same fort experienced the opposite – freedom!

Four generations after Christopher’s death, one of his second great grandsons, Josiah Holleman, lived on the patented land, in the northwest corner of Isle of Wight, near Mill Swamp.  

Reflecting the growth of human bondage as a norm, Josiah owned 9 slaves on the 1810 Isle of Wight census; no other information listed.  One year later, he bought Negro woman Harty and Negro girl Levinia in a complicated 3-way transaction.

For decades, the plantation economy built on slavery at Mill Swamp prospered, but eventually farming practices at the time depleted Virginia soil and led to economic destress such as experienced when Josiah Holleman died in debt in 1840s.  This situation would affect the future of Isaac. - Susan G. White

Part II of the Saga of Isaac and Ann Gray Holleman by Susan G. White follows in our next blog.