Hester Cummins was born in Mississippi roughly around 1796. Little is known about her parents, but she was described as “mulatto” in the census and as “light skinned” in the Police Board records. She was close to her sister and niece and free Black barber and diarist William Johnson wrote that she bought them for $1000. Had Johnson not casually mentioned this fact in his diary, little remaining evidence would have remained to supplement the 1840 census listing with Cummins as the household head and two slaves. No doubt historians would assume they were personal servants, rather than family members she bought and doubtless at a later date, emancipated. Given that the laws of Mississippi did not provide for emancipation without a special legislative act, it was an extremely complex process to free the enslaved, and Cummins surely held her sister and niece out of a sense of protection.

Cummins was a close friend of the Johnson family and visited frequently to socialize and to sit with them throughout periodic sicknesses of their children throughout the 1830s and 1840s. She also borrowed money from Johnson, and he would at times perform financial services for her like paying her taxes. Like the Johnsons, she also held enslaved people for economic reasons. In 1850, she held a total of nine enslaved persons, and eight years later, she sold ten enslaved women and children, along with some land for a profit of three thousand dollars. Cummins’s case, indeed, illustrates the complicated matter of enslavement by free Blacks. She concurrently held family members in slavery to liberate them at some future time while simultaneously reaping the labor and revenue associated with owning and later selling bond people.