The Winn family, headed by its patriarch Baylor, had migrated from King William County Virginia to Natchez. A countywide census in 1850 reveals that the then 52-year-old Baylor, recorded as a white man, had a young white wife, Elizabeth, and five children nearing or of adult age: Jasper, Calvin, Emeline, Sarah, and Mary. Contrary to the census, Winn and his family were in fact passing as white. When questioned on his true heritage, Winn would later claim some Native American ancestry. Winn’s family in Virginia did have strong intermixture with the local Indian group, the Pamunkeys; however, documents from his home county list Winn as a “free Negro.”

Baylor Winn likely relocated to Natchez to shed his Black heritage and start a new life as a white man with unlimited prospects. While passing, Winn successfully voted, gave testimony in court, and married a white woman. He keenly understood the precariousness of his situation and sought to maintain the racial veil over himself and his family. Ironically, his efforts to this end would ultimately see him become estranged from his own children who he subsequently disinherited. Free black barber William Johnson, who was on friendly terms with the family, noted in his diary that Winn engaged in periodic domestic abuse against his children. Emiline died in 1851 while the remaining siblings married and entered into trades against their father’s wishes.

Land purchases by Johnson made the two families neighbours in the mid-1840s and border disputes soon followed. Despite Winn’s successful public deception, Johnson’s diary entries reveal that he was aware of Winn’s secret. During one such dispute in 1851, Winn murdered Johnson in front of the latter’s son and other witnesses. Unfortunately for the Johnson family, their position as known free people of colour prevented them from testifying against a “white” man. Despite two subsequent trials to ascertain Winn’s true heritage, ultimately his public white persona remained intact and after two years in prison he was released. Having made his position in Natchez untenable in light of Johnson’s standing amongst the community, Winn relocated with his wife to Texas and lived out the remainder of his days as a white enslaver. He left all his property to her stating that “it is my will and desire that my children namely Jasper, Calvin, Mary, and Sarah have no part of my property, lands and effects of which I may have at my death.”