It is likely that James & George Winchester brought at least one or two enslaved people with them when they arrived on the western frontier in 1785.
However, the first record of the brothers purchasing an enslaved person in Sumner County occurred on July 3rd, 1788 when they paid James Bosley 150 pounds for “a certain mulatto boy named Dan about 15 years of age.” Roughly a year later, the brothers bought “a Negro woman aged about nineteen years, named Amie, and her male child about thirteen months named Ned” for three hundred dollars, which equates to nearly $9000 in 2020. James was also participating in the sale of enslaved people, indicated by the sale of an enslaved man named Harry to James Clendenning in 1796. It is unclear how many people James Winchester owned when Cragfont was completed in 1802, but a house of such size would have required a number of enslaved house workers to clean, take care of the children, cook and see to guests. The Winchesters speak little of the enslaved workers in their letters, but we do have reference to Delphy being the cook in a Winchester granddaughter’s memoir. Additionally, a young enslaved woman named Fanny is spoken of often in that memoir. She seemed to primarily work as a nanny and general house help during the 1840s up to the Civil War. In this same memoir, the slave quarters were described as being built of brick in a long row, a chimney between each with the cabins consisting of one large room, a big fireplace, and a loft. A garden plot for each family was located behind the quarters. Two log cabins, likely leftovers from Fort Tuckahoe, were fairly close to the house and utilized for enslaved domestic workers. James Winchester died in 1826 and an inventory of his personal property was completed two years later. That inventory listed twenty-six enslaved people and their ages at the time of the document. Comparing this to census records from the 1870s and 80s shows that a number of African-Americans named Winchester residing in Sumner County at that time were formerly enslaved at Cragfont.
We know little about the lives of enslaved individuals at Cragfont. However, we do know that James Winchester was an active participant in the buying and selling of people and built much of his wealth with the aid of stolen labor. Documents show that the mercantile store of Winchester and Cage, not only owned enslaved people, but also facilitated and negotiated the sale of people just as they did the sale of books, tobacco, cotton, and other goods. In 1806, two flatboats carrying goods for Winchester and Cage bound for New Orleans listed their cargo as eighty bales of cotton, fourteen hogsheads of tobacco, twelve thousand staves, and four enslaved women.