George Winn was one of numerous free men of colour to marry a white woman with little apparent controversy in Natchez. George and his wife had three children: Winslow, Helen (Ellen) and Mary (also known as Polly). Winn was the proprietor of a cotton plantation and a woodyard. The Adams county census of 1816 attributed ownership of ten slaves to Winn, a number that would increase over the course of his life. Upon his death in 1831 Winn did not manumit any of his slaves, the number of whom had increased to fifteen. Instead, these individuals were to continue working for the benefit of the Winn family. In addition to the enslaved, Winn bequeathed to his family an estate totalling approximately 1,200 acres.

In his will, George made provisions for his three children to be educated to a high level outside of the state. Helen Winn was sent to boarding school in Pennsylvania, where she studied French, music, and other subjects for five years. Her brother Winslow was also sent to a similar institution in the same state. Mary, although placed with a “decent family” within Natchez to continue her education, evidently resented the degree to which her own windfall appeared to differ from that of her siblings. Mary sued the white executor of her father’s will, Peter Lapice. This was but one of many disputes the Winn children had with Lapice. Mary married a white overseer William Mosbey in 1835 and Helen later married Washington Ford, a white farmer. The bitterness over Lapice’s perceived mismanagement of Winn’s estate persisted throughout the years, carried on by Helen and Mary’s husbands. William Johnson bought some of the family lands in the 1840s and continued friendly relations with them until his own death in 1851.