In the power relationship between America’s enslaved people and their enslavers, it’s widely assumed that the planter class held all the cards. After all, they were the dominant group who frequently enforced their will with whips, chains, dogs—and worse. Most enslaved people were considered little more than legal property, business investments whose human needs and family relationships were relevant only as far as they affected productivity and the bottom line of the people they served.

So when faced with the question of whether enslaved people could negotiate any aspect of their lives with their enslavers, the prospect seems hard to imagine. With power stacked so overwhelmingly against them, what could the enslaved negotiate for—and with what leverage? How could an enslaver concede even small favor to one, while maintaining fear and order among the broader ranks? The reality was complicated: In navigating lives of privation and brutality, enslaved people haggled, often daily, for liberties small and large, from rare personal time to less harsh treatment for themselves or family members, even to being set free.

The case of Sally Hemings and America’s third president Thomas Jefferson shines a light on this little-discussed aspect of America’s “peculiar institution.” Hemings’ story is an extraordinary one—since it chronicles not only a 16-year-old enslaved girl who had the life experience and presence of mind to negotiate for her unborn children’s future freedom, but a founding father whose complex moral code moved him to honor his agreement with a woman he enslaved for decades.

Hemings was Jefferson’s concubine, a woman who bore him six children, of whom four survived. Hemings’ role was to attend to Jefferson’s clothing and his chamber, which probably brought her into the main house often—and in very close proximity to Jefferson and his bed.

According to written accounts from their son Madison, Hemings accompanied the Jeffersons to France starting in 1787, when she was 14 years old. There she enjoyed certain privileges and saw the kind of freedom she wanted for herself and her future children. Thus, when Jefferson asked her to return with him to Virginia two and a half years later, she refused. It was possible for an enslaved person residing in France to sue for their freedom, since American slavery laws were not recognized or upheld there.

It’s unclear whether Hemings’ refusal was an overt bargaining chip or not, notes historian Annette Gordon-Reed of Harvard, who has written extensively of the Jefferson-Hemings relationship. Hemings was 16 and pregnant with his child. But Jefferson made a “solemn pledge” to her that if she returned, she would be granted “extraordinary privileges” and their children would be freed at age 21. Madison Hemings described their agreement as a “treaty.”

Even as a young expectant mother, Hemings understood the importance of her “future increase”—the term traders used in valuing unborn children. Childbearing mothers held different sets of monetary values than other women, based on their capacity to give birth to healthy children. Enslavers brokered deals for enslaved women based on projections of future breeding capacity. They questioned, examined, touched and did all they could to determine whether they were purchasing fertile women.

That Hemings understood this at age 16 is not surprising. By age five or six, most enslaved children had witnessed or even experienced family separation. Their parents often raised them to understand that their bodies were viewed as commodities, despite their humanity. Most young girls approaching puberty knew that their bodies were the focus of financial calculations, negotiations and under-the-table deals. So Hemings’ response to Jefferson’s proposal confirms that enslaved women and girls used what little leverage they had to carve out a better place for their future children. It’s likely she knew that her own mother had made a similar calculation, having been engaged in a long-term concubine relationship with Jefferson’s father-in-law John Wayles. (Hemings was reportedly a half-sister to Jefferson’s wife Martha, a fact that may have influenced his favorable treatment toward her.)

In order to understand the deal Hemings struck with Jefferson, nearly 230 years ago, it is useful to look at how other enslaved people negotiated small pockets of freedom within the institution—keeping in mind that the U.S. system of chattel slavery was in no way benign. Revolving as it did around crops, labor, land, domination, power and capital, it was an institution that exploited the labor—and disrupted the families—of those enslaved. Yet it was also an institution where people interacted with one another on a daily basis to discuss labor assignments, work incentives, food rations, disciplinary action, family visitation, geographic mobility and a host of other topics.

Enslaved people like Hemings learned how to operate within the system’s unending stream of delicate daily negotiations. Not that it was easy. They experienced few, if any, freedoms—and barely any room to exercise their personhood. Enslavers used an array of violent and manipulative tactics to make people work for them, most commonly the whip and the threat of sale and family separation. Many enslaved people resorted to acts of resistance, large and small. They liberated themselves by running away; they faked ignorance to avoid certain kinds of work; they broke tools and stole weapons; they took food to supplement meager diets; they became literate to write passes. Some turned to violence: rebellion, arson, poisoning and even murdering those who kept them in bondage.

But they also had direct transactional conversations with their enslavers and overseers, where they negotiated to carve out precious moments of liberty with the hopes of eventually becoming free.

Among the most complicated “relationships” during slavery were the intimate ones between enslaved women and their white enslavers. “These relations ran the gamut from rape and sodomy to romance, from chance encounters to obsession, concubinage and even ‘marriage,’” notes Brenda E. Stevenson, a professor of history at University of California, Los Angeles.

For the most part, scholars refer to the enslaved women in these relationships as “concubines.” Often described as attractive mixed-race women who planters saw as desirable, many worked in the domestic realm, wore finer clothing than most enslaved women and experienced their first sexual encounter as a result of this “relationship.” History has recorded the names of many such women forced to be concubines—among them, Sally Hemings and her mother Elizabeth Hemings, Corinna Omohundro, Elizabeth Ramsey and her daughter Louisa Picquet, Julia Dickson and Elizabeth Keckley. Some shared their experiences in narratives, while others’ stories appear in the autobiographies of relatives or were buried in the private papers of their enslavers.

In North Carolina, Harriet Jacobs became one white man's concubine, hid in a tiny attic garret for seven years and fled to the north, all to avoid being sexually exploited by her enslaver and to keep her children out of slavery. She later published a book called Incidents in the Life of a Slave Girl, becoming a prominent abolitionist and one of the first people to publicly broach the topic of sexual harassment of enslaved women.

We cannot know whether or not these exchanges were consensual, but we do know that enslaved women were usually the property of the men who exploited them, and this fact alone complicates our interpretation of this history. It’s hard to ignore the power dynamic involved, the often-significant age gap, the sometimes-incestuous connections or the varying social status of all people involved in these “connections.” It’s even difficult to find appropriate nouns to describe them: “unions” and “relationships” seem presumptuous while “interactions” and “exchanges” seem benign, given that many concubines were sexually abused.

But despite the inherent power imbalance, some enslaved women used these forced interactions to find a better space for themselves, or secure freedom for their offspring. Some might have entered (assuming they could go into these willingly) these “unions” in order to escape the auction block, the field or other work spaces. But could enslaved women “enter” such relationships? Did they have a choice? If they did, could they exercise it? What was their negotiation angle?

Foremost was their capacity to bring new lives—and laborers—into the world. In an economy where black bodies were commodities, childbearing women were crucial economic multipliers. If they reliably added to their enslaver’s net worth, perhaps they could earn small privileges for themselves and their family—such as time off to nurse newborns or care for sick children, or visit a family member at a nearby plantation. And concubines who bore children to their white enslavers could sometimes leverage those deeper familial connections to secure better situations for themselves and their offspring, such as relief from certain work assignments, the chance to be educated and eventually set free. However, enslaved women who tried to leverage this power, and these interactions, had varying degrees of success. And these strategies were not always premeditated, as many enslaved women dreaded the idea of motherhood and preferred not to bring children into a world of captivity.

For mother-daughter concubines Elizabeth Ramsey and Louisa Picquet, known to us through Picquet’s 1861 published narrative, the hurdles were formidable. Elizabeth, owned by the Randolph family of South Carolina, found her negotiating powers superseded by the financial and personal challenges of the white families she served. When she gave birth to James Randolph’s daughter Louisa, it did not take long for his white wife to figure out that the two-week-old baby looked like her husband. Elizabeth and Louisa were quickly sold.

Elizabeth, about 20 years old, then became concubine to her new owner, David Cook of Georgia, even though he too was married and had a family. Together, they produced three children. But after Cook incurred debts and lost his property, he sent his wife and children to live with relatives while he fled to Alabama with his concubine and her daughter. By the time Louisa was 14 years old, Cook forced himself on her. When she resisted, she suffered severe whippings. The family was separated and sold when Cook’s debts caught up with him. Ramsey tried to negotiate for them to be purchased together, but she and her son were sold to an enslaver from Texas, while Louisa went to a Mr. Williams of Louisiana.

Of the last goodbye, Louisa said her “Mother was right on her knees, with her hands up, prayin' to the Lord for me. She didn't care who saw her: the people all lookin' at her,” knowing she would likely never see her daughter again.

Mr. Williams, who was in his late 40s, let Louisa know right away that he intended to spend the rest of his life with her. She resisted and tried to negotiate with him, but he was relentless. Reflecting on this painful experience, she “wished he would sell me…because I had no peace at all. I rather die than live in that way.” But Williams “got awful mad and said nothin' but death should separate us; and, if I run off, he'd blow my brains out.” Louisa’s life with Williams was so miserable, she longed for her mother and prayed for his death.

When her second prayer was answered, she was freed and spent time trying to find her mother. Picquet moved to Ohio, married a mulatto man and became active in the church. She exchanged letters with her mother—who, she discovered, had been negotiating her own price so that Louisa could come to Texas and purchase her. In the first letter Louisa received, Elizabeth wrote: “Col. Horton would let you have me for 1000 dol. or a woman that could fill my place; I think you could get one cheaper where you are that would fill my place than to pay him the money; I am anxious to hav [sic] you to make this trade.” As negotiations continued, Louisa wrote directly to her mother’s enslaver, requesting he lower the price since Elizabeth was aging. He responded by telling Louisa that she had no bargaining power and that while Elizabeth was getting old, “she carries her age well, and looks as young as she did 20 years ago.” He did, however, volley back that he was willing to participate in a direct trade of “another [enslaved woman] of her quality and qualifications in her stead.”

For nearly two years, the mother-daughter duo continued negotiating with Elizabeth’s enslaver while Louisa went on a fundraising tour throughout Ohio and New York, seeking money to purchase her mother. At one point, Horton lowered Elizabeth’s price to $900, but both women were heartbroken to learn that Louisa’s brother John and Elizabeth’s husband were not for sale. In the end, Louisa successfully completed the transaction and purchased her mother. The two were elated to be together, but disappointed that the family was not intact.

No negotiation had higher stakes than when an enslaved person tried to buy themselves—or their loved ones—out of slavery. Unless an enslaver was desperately hard up for money, power lay squarely on his/her side and there was little an enslaved person could do to change the calculation. Several generations of the Hill family of Virginia, for example, spent their lives trying to purchase a release from bondage. After negotiating a price, John Hill’s two uncles tried to pay their enslavers for their freedom, but they were shocked to learn that the enslavers had upped their price.

Similarly daunting challenges faced another Virginia man named Dangerfield Newby, one of John Brown’s “black raiders” on Harper’s Ferry. Newby, who had himself been released from slavery by his white enslaver-father, was trying to purchase his wife Harriet and their seven children, who lived more than 50 miles away. Harriet appeared to have been trying desperately to broker a sale between her own enslaver and her newly freed husband. In a letter found on Newby’s body when he died at Harper’s Ferry, she was begging him: “I want you to buy me as soon as possible, for if you do not get me somebody else will… it is said Master is in want of monney [sic] if so I know not what time he may sell me, an’ then all my bright hops of the futer [sic] are blasted.” Unfortunately, Dangerfield wasn’t able to complete the transaction, having raised just over $740 of the $1,000 price for her and one child. She was sold after the raid.

There were many documented cases of successful buyouts. But Newby’s history, and that of the Hills, reflected the fundamental challenges of negotiating to purchase one’s freedom. The outcome of such deals rested on two exceedingly difficult things: first, on their enslavers’ promises, which were subject not only to changing self-interests, but to the optics of control they needed to display to others whom they enslaved. Second, those eyeing a way out of enslavement needed hefty sums of money, a huge hurdle. Many, like Louisa, had to turn to the charity of Abolitionists.

Negotiations during slavery took on many forms. Sometimes they were successful. The vast majority were not. It is clear from these stories that enslaved people did all they could to maintain their family units, and they often had to make difficult choices. Understanding these interactions shows the complexities of slavery and the savvy ways enslaved people negotiated their status within the peculiar institution.

Daina Ramey Berry is the Michael Douglas Dean of Humanities and Fine Arts at the University of California, Santa Barbara. She is a scholar of the enslaved and the award-winning author/editor of books on slavery including The Price for Their Pound of Flesh, the Value of the Enslaved, from Womb to Grave, in the Building of a Nation. Follow her on twitter @DainaRameyBerry.