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This past summer, I was asked to present at the Lemon Project Summer Sankofa Genealogy Workshop held at William & Mary’s Swem Library. As I normally do, I prepared for my presentation by searching within the Virginia Untold collection to identify a research scenario demonstrating a variety of records. Inevitably, the records run out and the research journey must continue beyond Virginia Untold. These presentations are an opportunity to point out the potential of Virginia Untold, as well as its limitations allowing me to highlight additional resources from the Library of Virginia and peer institutions.

In this case, I was able to find a great deal of sources digitized through Virginia Untold relating to a family from Petersburg City. What made this particular research journey so remarkable is a real-time discovery we made during the event at William & Mary. The Lemon Project also hosted Nicka Sewell-Smith, Senior Story Producer at Ancestry.com. Sewell-Smith helped me find a missing link connecting and confirming the relationship of individuals in this Petersburg family to New Orleans. I knew a blog post was in demand.

My research journey began by finding the registration of John Shields, a ten-year-old boy,  recorded in the Petersburg City “Register of Free Negroes” on April 21, 1859. I’ve seen children recorded in other localities and other “Free Negro Registers.” They are often identified alongside parents and sometimes in reaction to local events. There’s evidence to indicate that parents sometimes registered their children for fear they might be arrested or trafficked as enslaved people if not entered into the court. Shields appeared to be recorded alone. I was intrigued by this entry because I couldn’t find record of a mother or a family member in entries dated from that same year. There were other young people recorded around in the 1850s but they were in their late teens—an age one might expect free Black men and women to register as they came of age and desired proof of their freedom. Tax registrations were required on “negroes twelve and older” which may have also been informally applied for registering as a free person.1 But this wouldn’t have applied to Shields who was only ten years old in 1859.

Shields’ registration described him as “four feet 9 ½ inches high” and of a “bright mulatto complexion.”

Petersburg (Va.) Register of Free Negroes and Mulattoes, 1859-1865. Local government records collection, Petersburg City Court Records. The Library of Virginia, Richmond, Va. 23219.

Shields’ registration stated that he was freed by a deed of emancipation and I assumed I might find one in Virginia Untold. A simple name search for “John Shields” resulted in a few hits, the first of which was a deed of emancipation. (Quick note: we’ve yet to digitize all the loose deeds of emancipation in each locality. If you can’t find a deed of emancipation in Virginia Untold, it still might exist as loose record or recorded in a deed book. Deed books tend to be more reliable than the loose deed collections. For example, I used FamilySearch’s new full text search feature to search for James May and found additional deeds involving enslaved people that we don’t have digitized in Virginia Untold.) The deed revealed that Shields’ enslaver James May emancipated him in March 1859. The deed was recorded in court on April 21, 1859—the same day Shields was registered as a free person. The deed of emancipation was crucial in that it provided the name of Shields’ mother. May described Shields as a “slave boy…son of my woman Dolly Shields.”2 I had another name!

A search for “Dolly Shields” in Virginia Untold immediately revealed a hit. But this time not a deed of emancipation, as I assumed, rather a bill of sale. In 1854 (five years before her son would be emancipated), James May sold John’s mother, Dolly Shields to a woman named Catherine Robertson from New Orleans. John Shields was five years old when May sold his mother. At first glance, I assumed Catherine Robertson was a female enslaver, perhaps taking part in the domestic slave trade by purchasing enslaved people from the upper Southern regions of the country, such as Virginia and Maryland to sell or farm land in the deep South. But a closer read exposed an important detail in the manuscript: someone had inserted the phrase above Dolly’s name, “the mother of said Catherine.” Catherine Robertson was not a random person from New Orleans. She was the daughter of Dolly Shields and she was buying her mother.

Know all men by these presents, that I, James May of Petersburg Virginia, in consideration of fifty Dollars paid me by Catherine Robertson of New Orleans, have sold + do hereby grant to said C. Robertson a negro woman slave called Dolly or Dolly Shields [inserted above: who is the mother of the said Catherine] the right + title to which said slave I warrant unto said Catherine Robertson agst all persons. whatever- Witness my hand + seal this 14 of August 1854. James May

My next instinct was to search Virginia Untold again but this time for Catherine Robertson. Who was this woman? Based on results from another name search, Catherine made a similar purchase in the year she purchased Dolly! She bought an enslaved man named Lot Stracheon from James Lynch also in Petersburg. The document provided few other clues, but I couldn’t help wondering if Catherine and Lot were also related. If Dolly was Catherine’s mother, could Lot have been her father?

Without many other results for Catherine Robertson, I decided to pursue the enslaver. (Note that I could have done some additional name searches for Catherine and her surname as it could be spelled differently in different records). It’s crucial to learn as much as possible about the enslaver and their family, economic, and social history. Were they selling or deeding other enslaved people? Did they deed their enslaved people to family members? By searching the name “James May” and utilizing a few facets to narrow my search, I discovered that May was involved in seventeen different transactions involving enslaved people from 1839 to 1859. The majority of these transactions were emancipations, but he was also buying and deeding individuals during that time. The oldest person emancipated was a man named Thomas Bolling, age 45 and the youngest was two-year-old girl named Elizabeth, the daughter of Joanna. Furthermore, searches in the Petersburg deed books fully digitized through Family Search reveal even more transactions involving May and enslaved people.3

This information about May was intriguing, but it didn’t tell me much about John, Dolly, or Catherine. I was beginning to exhaust the limits of Virginia Untold. I decided to pivot my search in the opposite direction using census records to locate these individuals after the Civil War. By 1870, I knew they would all be considered legally free and thus (likely) recorded in the U.S. census.

I used Ancestry.com to search for census and vital records and I found a few possible clues that Dolly was living in Petersburg with her husband, Edward Shields in 1870 and 1880, but her age and the fact that she was in Petersburg rather than New Orleans confused me. According to the bill of sale, Catherine was living in New Orleans when she purchased Dolly in 1854 and presumably, she would take her to Louisiana upon purchase. Did Catherine purchase her mother and emancipate her in Petersburg? Or perhaps Dolly traveled back to Virginia to settle after the Civil War?

I also used Ancestry.com to search for Catherine Robertson in New Orleans and John Shields in Petersburg but I came up short. I shared my frustration during my presentation to bear out the challenges of researching enslaved people. I concluded with a few possible avenues for searching additional collections but ultimately recognized that I had reached the limits of Virginia Untold.

Little did I know that Ancestry’s Senior Story Producer, Nicka Sewell-Smith was sitting in the back row of the presentation room searching for Catherine Robertson in New Orleans while I wrapped up the Q&A…

Sewell-Smith understands how to leverage both Ancestry and FamilySearch, the latter being a resource I sometimes overlook. Sewell-Smith is also from Louisiana, which makes her familiar with the types of records available for this state, particularly New Orleans. It was great to have her in the room that day because she was able to demonstrate to participants in real time how to navigate these large aggregate sites. Sure enough, Sewell-Smith found an 1870 census record documenting a mixed household in New Orleans including both a Catherine Robinson and a John Shields!

Sewell-Smith found this record using Family Search rather than Ancestry.com

``Orleans, Louisiana, United States records,`` images, FamilySearch (https://www.familysearch.org/ark:/61903/3:1:S3HY-67D7-HZV?view=explore : Nov 7, 2025), image 193 of 809; United States. National Archives and Records Administration. Image Group Number: 004269437

Sewell-Smith also knew to search for name variations recognizing that Robertson is often changed to Robinson and vice versa. We now had reasonable confirmation that brother and sister John Shields and Catherine Robertson were living together after emancipation. Some of the household members don’t appear to be related biologically. The listed head of household was William Normand, described as a “steamboat man” born in Prussia. Below Catherine’s entry, a man named George Robinson was listed as a domestic servant and approximately the same age of Catherine—perhaps her husband? George was born in Louisiana. There was another woman identified named Mary Robinson, relation unknown; she was born in Missouri. Other members of household were born in Maryland, Louisiana, and Tennessee. And finally, the very last entry is John Shields, born in Virginia, occupation: barber. He was recorded as twenty-three years old in 1870, born around 1849—his approximate birth year from the Petersburg City, “Register of Free Negroes.”

If Catherine’s family was from Petersburg, how did she get to New Orleans? Sewell-Smith suspected that James May sold Catherine to the deep South when funds became tight. But I also think May was purchasing enslaved people to free them, like in the case with Charles Woodleif, who May states was the son of a free man of color.

I could not find any record of May having owned or emancipated Catherine. We might assume Robertson was not her maiden name. If she was sold south as Sewell-Smith believed, New Orleans may have provided upward mobility for Catherine, allowing her to purchase her freedom and then purchase her mother Dolly out of slavery. In the 1870 New Orleans census record, Catherine is the only person recorded as having any real estate. In fact, the property belonged to Robertson (Robinson) and her personal value was indicated as $500—a substantial value for 1870.

There is certainly more to be explored around James May, and because he was a free white man in the early nineteenth century, there are likely records to document his decisions. We also can’t dismiss the possibility that May was the biological father of the people he emancipated or sold, including Catherine.

Taking cues from Sewell-Smith, I found another possible census record for John Shields living in New Orleans in 1880. He is listed as the head of his own household along with his wife Elizabeth (32), son Edward (7), and daughter Deborah (4). Interestingly, the 1870 and1880 census record for Dolly Shields in Petersburg listed her husband as Edward. Could John have named his son after his father?

By 1880, John Shields was married with two children living in New Orleans.

``Louisiana, United States records,`` images, FamilySearch (https://www.familysearch.org/ark:/61903/3:1:33SQ-GYBD-6K1?view=explore : Nov 7, 2025), image 184 of 865; United States. National Archives and Records Administration. Image Group Number: 005160720

As ever, many questions remain. How did Catherine Robertson get to New Orleans? When did John move to New Orleans to be with his sister Catherine? Why did Dolly choose to stay behind? Were there other family members that remained in Petersburg or traveled to New Orleans? And what to make of Catherine’s purchase of Lot Stracheon? While some details may never come to light, I feel more confident these days that we can find answers. More records are increasingly becoming more accessible. And maybe more importantly, more people are engaged in this research and storytelling. What other places might we search for Dolly and John and Catherine? What ideas do you have for telling more of their story?

Lydia Neuroth

Project Manager - Virginia Untold

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