Isaac Holleman was my fourth great-grandfather on my maternal grandmother’s paternal line. One of the earliest records I found bearing his name came from the Freedmen’s Bureau. The document included the October 6, 1866 request for transportation from Fortress Monroe in Hampton, Virginia, where he had been classified as “contraband.” Traveling with him were his wife Ann and three children: Robert, Moses and Ada. Ada Holliman was my third great-grandmother.

What I didn’t understand at first was the story of the children’s mother. The mother of Robert, Ada, and Moses was Malinda, but for a long while she was almost a ghost in my research. I assumed it would be very difficult to find her because it never occurred to me that she wasn’t enslaved.

I connected with the Holliman family through Susan White, who had uploaded her research to Ancestry.com. On Susan’s family tree, Malinda was listed with the surname Pretlow. When I checked the 1860 census, Malinda Pretlow and her children—Robert, Ada, Moses, and Isaac—were enumerated as free in Southampton County. There is a Virginia Pretlow listed as 18 years old in the household as well, whom I need to investigate.

Susan is a descendant of Josiah Holleman, the man who enslaved—and very likely fathered—Isaac. In 1836, Josiah formally manumitted Isaac, allowing him to live as a free man.

His freedom proved temporary. Josiah Holleman died in debt around 1854, and to satisfy those obligations, Isaac was sold back into slavery for $355. If you look closely at the document below, you can see that he was sold to R.A. Urquhart, who also purchased a black mule for $55 and two apple trees for $26.16 and $1.75.

During this time of re-enslavement, Isaac partnered with Malinda Pretlow, who was free, and together they had three (3) surviving children.

At some point during the Civil War, Isaac liberated himself and fled to Fortress Monroe, one of the earliest contraband camps where enslaved people sought refuge behind Union lines. When he fled, Isaac brought with him his new wife Ann—and, inexplicably, his free children. Why he did so remains a mystery. Perhaps he feared their freedom would not be respected if he escaped alone. Isaac, himself, has been freed and then returned to slavery.

In 1866, he requested transportation back from Fortress Monroe through the Freedman’s Bureau (above). In 1870, after Isaac returned to the south side of the James River, he purchased 50 acres of land in Windsor, near the Nansemond County line, for $194 (with 12% interest). He and Ann went on to have many more children: Luzerne, Nonnie, Addie Lou, Isaac Thomas, Jeremiah, Joseph, Joshua, John Henry and Joanna. The land remained in the Holliman family until the 1960s.

Below is a Civil War map showing the location of the land.

Sources:

• “Virginia, Freedmen’s Bureau Field Office Records, 1865-1872,” database with images, FamilySearch (https://familysearch.org/ark:/61903/3:1:S3HT-XCSQ-FKJ?cc=1596147&wc=9LMLN36% 3A1078519202%2C1078520304 : 25 June 2014), Fort Monroe (assistant subassistant commissioner) > Roll 128, Letters sent, vol 1-2, Mar 1866-May 1868 > image 68 of 158; citing NARA microfilm publication M1913 (College Park, Maryland: National Archives and Records Administration, n.d.).
• The National Archives in Washington D.C.; Record Group: Records of the Bureau of the Census; Record Group Number: 29; Series Number: M653; Residence Date: 1860; Home in 1860: East Side Nottoway River, Southampton, Virginia; Roll: M653_1380; Page: 5; Family
• “Virginia, Isle of Wight County Records, 1634-1951.” Isle of Wight County Courthouse, Isle of Wight. Roll 39
• Isle of Wight County (Va.) Chancery Causes, 1767-1966 (bulk 1872-1919), Nancy Holleman WIDOW ETC vs. EXR OF Josiah Holleman ETC, Index 1855-001
• “Virginia, Isle of Wight County Records, 1634-1951.” Isle of Wight County Courthouse, Isle of Wight. Book 42, Page 92-93, Roll 137
• Confederate States Of America. Army Of Northern Virginia. Engineer Office, Bien, J., Campbell, A. H. & Patton, J. H. (1891) Preliminary map of a part of the south side of James River, Va.: from surveys and reconnaissances. [Washington: GPO, between to 1893] [Map] Retrieved from the Library of Congress, https://www.loc.gov/item/lva0000171/.