At least two people were enslaved at what is now Duke Homestead: Caroline, whom Washington Duke purchased, and Jim, whose labor he leased. While most people today imagine slavery as dozens to hundreds of people laboring on a plantation, it was also common for a couple enslaved people or an enslaved individual to live and work on small farms and in city dwellings and businesses. In 1860, over 5,000 people were enslaved throughout Orange County, and many of them labored on small farms like Duke Homestead.
Washington Duke purchased Caroline in 1855. Based on the amount he paid for her, she was probably young, perhaps 11 or 12 years old. When Duke purchased her, Caroline was separated from her mother and sister. On a small farm like Duke Homestead, she was probably the only enslaved person living there. Caroline likely performed tasks like cooking, cleaning, and taking care of the children, but she may have also worked in growing and harvesting crops during the busy season.
It is not known what happened to Caroline after 1855. Washington Duke does not appear as an enslaver on the 1860 Slave Schedule of the Census, so he may have sold her by that time. However, he also does not appear on the 1860 Agricultural Census, so it is possible that census workers simply failed to record him that year.
There are some clues what happened to Caroline. When Washington Duke died in 1905, he left property to his housekeeper, an African American woman named Caroline Barnes. After emancipation, many formerly enslaved people continued in the same kinds of work they had been forced to do before the war, and often on the same properties or for their former enslavers. There is still more research needed to confirm, but it is likely that this Caroline Barnes is the same Caroline that Washington Duke had enslaved decades earlier. On the marriage certificate for Caroline Barnes, her mother is listed as Gracy, which is the same name of the mother of the enslaved Caroline (you can see her mother and sister, Gracy and Emiline, listed above Caroline's name in the purchase record).
Jim was born into slavery around 1830, growing up on James W. Cox's plantation in Kinston, NC. Starting around 1860, he was "hired out" or leased to small farmers in Orange County. Leasing of enslaved people was very common in the North Carolina piedmont. In the usual arrangement, smaller farms would lease the labor of an enslaved person from a wealthier planter for a set period of time, often one year or for a growing season. The smaller farmer paid the wealthier planter for the labor of the enslaved person. Leased enslaved people like Jim were separated from family and loved ones and moved to new enslavers every year, year after year. While on Washington Duke's property, Jim worked in farming tasks, like growing and curing tobacco.
When he was leased out, Jim continually resisted enslavement. In a letter to his slaveowner James W. Cox in 1860, T.B. Morris, whom leased Jim at the time, complained that Jim worked intentionally slowly and damaged crops. These were both common ways that enslaved people resisted slavery. Jim also ran away at least three times, once from Morris in 1860 and twice from Washington Duke in 1863. It is likely he was not running north, but rather hid himself temporarily to visit missed loved ones enslaved on other properties. Seeking freedom did not necessarily mean heading to the north, but could also mean defining their own terms of their freedom to visit family when they wanted, and not asking for permission or passes from the slave holder.
At least once, however, Jim did try and escape to full freedom, in attempts of "self-emancipation." In June of 1863, six months after the Emancipation Proclamation, Jim ran away with three other people: Green, enslaved by Washington Duke's brother, William; Lear, Green's wife; and Lear's child. They were trying to reach Union lines in New Bern, 140 miles away, where thousands of other people had escaped to and self-emancipated. It is unknown what exactly what happened, but Jim, at least, never reached New Bern, and was back at Duke Homestead by October 1863.
Jim continued to be leased out until the end of the war. When emancipation came, he was living at William Lunsford's farm, who had leased his labor. After the war, Jim took the name James Cox. He married his wife, Martha, whom he met while enslaved by Lunsford, and lived the rest of his life in the Durham area, working as a tobacco sharecropper.