From Slave to Independent Businesswoman (and Slave-Owner): The Complex Story of Anna Kingsley

Anna Kingsley was just thirteen years old when she “married” Spanish plantation owner Zephaniah Kingsley in 1807.

“Marriage” was hardly the proper term for the union, though.

Anna, born Anta Madjiguene Ndiaye, was captured in her homeland near what is now Senegal and brought to Cuba on a slave ship. She was then purchased by Kingsley, who was thirty years her senior.

Kingsley brought Anna back to his Laurel Grove plantation in what’s now Orange Park. Anna, still a young teenager, was pregnant by the time they got there.

It was clear early on that Kingsley looked upon Anna with much more favor than he did the rest of his slaves. She enjoyed a life of relative freedom at Laurel Grove; there were over a hundred slaves at the plantation, but only Anna and her children lived with Kingsley in his house.

She came to be a respected figure on the plantation, operating it seamlessly whenever Kingsley was away.

By 1811, Kingsley and Anna had three children together. Kingsley granted Anna and their children full legal emancipation. This ensured that they wouldn’t be considered property and sold off in the event of Kingsley’s death.

Enjoying her newfound freedom, Anna petitioned the Spanish government for – and was rewarded – five acres of land across the river in Mandarin in 1813. She set up her own operation on this property, even purchasing slaves to tend to her crops.

That same year, conflict flared up in the state between the Spaniards, who controlled Florida at the time, and American forces wishing to annex the state.

Kingsley was taken prisoner by the Americans, who seized Laurel Grove. He would eventually be released, fleeing to an unknown location. Anna managed to save herself, her children, and several slaves from the property – then burnt the whole thing down, along with her own land, to prevent the Americans from being able to use the land.

Kingsley would soon resurface, and purchased a plantation on Fort George Island in northern Jacksonville.

Anna joined her husband at the sprawling, luxurious Kingsley Plantation. And while Kingsley would take three other “wives” during their time at Kingsley Plantation, Anna’s status as matriarch was never in question. She lived in a space built above the plantation’s kitchen with her children, with a fourth child arriving in 1824. And she held a role similar to the one she held at Laurel Grove, assisting in overseeing slave labor and the plantation’s overall functionality.

By the 1830s, conditions in Florida had changed drastically. With the U.S. having taken over Florida in 1822, laws gradually began popping up to limit the freedoms of freed slaves, and to discriminate against mixed-race families such as the Kingsleys.

Kingsley fled to Haiti in 1835 to form a new plantation, and by 1838, Anna had joined him there. Their new plantation, in accordance with Haitian law, utilized indentured servitude rather than slavery.

In 1843, Kingsley passed away. Some of his family members moved to have Anna and her children excluded from any possible inheritance, citing racially-charged laws that failed to recognize mixed-race marriages as valid.

Anna returned to Jacksonville to fight back. And not only did she fight, she won, obtaining a court ruling that insured her the same legal treatment she would have received under Spanish rule. Anna and her children were rewarded their rightful inheritance – and Anna was also given ownership of several of Kingsley’s former slaves.

Unfortunately, rather than freeing them, Anna’s goal was to rent them out to other plantations – a plan that the court didn’t allow her to execute.

Anna would remain in Jacksonville for the rest of her life – with the exception of a stint where she and other free black people were evacuated from Jax by Union forces during the Civil War. She died in 1870 at age of 77.

Today, Anna and her family have a complicated legacy. As a multiracial, polygamist clan, they would stand out even in the modern-day South. The struggles they faced show the ugliest side of America, while her persevering spirit embodies Americans at their best. Anna was a strong, independent woman who made the best of an impossible situation – but also actively participated in the very system that led to her abduction. She was an abolitionist and a slave-owner, simultaneously.

Her story is complex, and like many others in America’s history, hard to judge fairly within modern context. But by any standard, her story is among the most remarkable in our city’s history.