Rachel Winston/Nelson was manumitted as per the wishes of her enslaver, the one-time Lieutenant Governor of Mississippi, Fountain Winston, following his death in 1834. The two had been engaged in a sexual relationship, that produced a child by the name of William ‘Bill’ Winston. Winston’s will dictated that the young William was to remain in the care of his mother to whom he granted a sum of $500 and other effects for their upkeep. It made provisions for the manumission of William, cited in the will as being “too white to be continued in Slavery,” upon his reaching the age of twenty-one. Thereafter, it granted him ownership of land in Tennessee. This arrangement appears to have been honored at least in relation to William’s manumission as both he and his mother were listed as “free Negroes” in the US census of 1850.

While aged twelve and still enslaved, the young William was sent by his mother to become an apprentice to William Johnson, the free black “barber of Natchez.” Winston developed a close relationship with Johnson and remained in his employ until the latter’s murder in 1851 and thereafter continued to work for the Johnson family. It seems that Winston was well regarded in Natchez and the Mississippi legislature in 1854 passed a special act that officially authorized him to remain in the state, which was unusual for free Black people in the politically tense 1850s.

Records indicate that the newly manumitted Rachel Winston may have struggled financially despite the provisions of Fountain Winston’s will. However, by 1857 with her son now fully grown, she appears to have attained secure financial footing. This is indicated by her purchase of a house and lot valued at $1000. William would later marry another free person of colour, Anna Leiper.