Her name was Nancy. She is mentioned in the Minute Book for the Washington County Court in November 1788. The entry reads “Record of Slave Sale,” and notes that a “subscribing witness” named David Allison testified under oath to the existence of a “bill of sale” from a man named Micajah Crews to Andrew Jackson for a “Negro woman named Nancy about Eighteen or Twenty Years of Age.”Footnote ¹

Andrew Jackson, of course, was the seventh president of the United States. However, in November 1788 he was a young man from an obscure family with little to his name. Only twenty-one years old, Jackson was in Washington County working as a “state's attorney,” or prosecutor, a position he garnered thanks to connections he had made in Salisbury, North Carolina, where he studied law. One of those connections, a young lawyer named John McNairy, had received a judicial appointment in North Carolina's western territory, which included everything west of the Appalachians to the Mississippi River, or what is today Tennessee. McNairy and Jackson travelled together to Washington County's seat of Jonesborough along with another attorney named David Allison, the witness to the sale, in the spring of 1788. McNairy then invited Jackson to join him even farther west at a remote constellation of settlements on the Cumberland River, or what would one day become Nashville, in October. Allison remained behind.

According to most accounts, Jackson purchased Nancy before leaving. Jackson's scholar Robert Remini posits that Jackson procured an enslaved woman to establish himself as a gentleman. “A gentleman needs a servant,” notes Remini, “so shortly after Jackson arrived in Jonesborough, he bought a female slave, Nancy, aged eighteen or twenty.” Most young white men procured male servants—not females—to signal status, leading historian Mark Cheathem to argue that Jackson “may have wanted female companionship or someone to cook his meals and wash his clothes.” Historian Dawn Peterson goes even farther, positing that Jackson “may have hoped that [Nancy] would increase his slaveholdings” by bearing him children.Footnote ²

She does not appear in Jackson's 1829 inventory of enslaved people, nor does she appear in his 1825 inventory of enslaved people. Nancy is not listed as sold in any of his business records, nor is she mentioned occupying a particular role in his household, which many enslaved people were, nor is there any mention of her death.Footnote ³

Jackson procured four other women of the same name, later in his life, but none correspond to the Nancy that Jackson acquired in Jonesborough in 1788. For example, a bill of sale exists showing that Jackson and his business partner Andrew J. Hutchings purchased an enslaved woman named Nancy from a man named John Orr on February 25, 1805, seventeen years after he acquired the first woman named Nancy in Jonesborough. Meanwhile, an inventory of Jackson's enslaved population in 1829 mentions a nine-year-old girl named Nancy, who happened to be the daughter of two other enslaved people that Jackson owned: Jim and Hanah. Finally, Jackson procured two female slaves named Nancy while President, one from a man named William Hebb (Old Nancy) and the other, a child, from Hebb's brother, George, in 1833 and 1834, respectively.Footnote ⁴

It is not even clear that she made it to Nashville. Jackson later claimed, for example, that he brought two horses, four guns, and various sundry items with him to Tennessee, but not a woman. All other accounts read as if Jackson arrived in Nashville alone, an unencumbered bachelor who boarded with a widowed settler, courted her daughter Rachel, and shared a cabin with another attorney named John Overton. Overton even confessed that he and Jackson shared the same bed, an arrangement that was common in the eighteenth century, but not something that left much room for a young, enslaved woman's “companionship.”Footnote ⁵

The “Record of Sale” provides a clue. According to it, David Allison testified under oath that Jackson bought Nancy on November 17, 1788. However, Jackson and his party had already left for the Cumberland settlements by then, traveling along the infamous “Wilderness Road” through the Cumberland Gap and then down the Cumberland Trace to Nashville, a harrowing journey that meandered for over two hundred miles and took two weeks to traverse. Court records corroborate this. On November 3, for example, Jackson's friend John McNairy admitted Jackson to practice law in Davidson County, where the Cumberland settlements were located, a ceremony that required Jackson to be physically present to take an “oath of admission.”Footnote ⁶

Of course, there was a two-week window between the 3rd and the 17th, which means Jackson could have taken his oath of attorney, hopped on a horse, and ridden quickly back to Jonesborough. But James Parton asserts that Jackson issued “seventy writs to delinquent debtors” within a month of arriving and spent the November term preparing for trial against a man named Thomas Hendrix. Even if that term extended into December, it is unlikely that Jackson could have traveled to Jonesborough and back—a four-week commitment—and completed these various legal tasks.Footnote ⁷

However, the staggered timing of Jackson's arrival in Nashville and Allison's testimony in Jonesborough may tell us something else about Nancy. It suggests, for example, that Jackson sent a message back to Jonesborough not long after arriving in Nashville, perhaps via the armed guard that escorted his party to Davidson County.

The legal record provides another clue. For all subsequent purchases of enslaved people that he made, Jackson retained a bill of sale, or receipt, that was then recorded in the county court of whatever county the sale took place. Courts played a central role in slave transfers in the South, as did bills of sale, for three reasons. One, as historian Jenny Wahl notes, “the high market value of slaves enhanced the likelihood of litigation,” meaning that buyers were more likely to sue sellers when there was a problem with a slave than with other acquisitions, say animals or machinery. Two, slave markets often involved significant information gaps, meaning sellers knew quite a bit more about the individuals that they were selling than did buyers, opening the door for fraud. And—finally—buyers and sellers were more evenly matched in the slave trade than in other commercial settings, meaning they were more likely to adjudicate their disputes in court.Footnote ⁸

As a lawyer, Jackson probably understood all this, and therefore recorded bills of sale for the enslaved people that he acquired over the course of his lifetime. For example, the records of Davidson County indicate that Jackson received a bill of sale for an enslaved man named Tom “about Seven and Twenty years old” on July 7, 1791, three years after acquiring Nancy. Davidson County court records also indicate that Jackson received a bill of sale for a second enslaved person, a young boy named Aaron, on December 21, 1792, four years after acquiring Nancy.Footnote ⁹

However, the Washington County court recorded no actual, physical bill of sale for Nancy, only that David Allison testified—under oath—that such a bill of sale existed. This means either that Jackson did not have a chance to record the bill of sale in court and subsequently lost it, or he never had one. Allison's testimony suggests the latter. Not only did he lack a bill of sale, for example, but he also lacked a price. Almost all Jackson's acquisitions of enslaved people recorded a price. Court records indicate that Jackson paid £60 for Tom and £100 for Aaron in 1792. He then paid $150 for an enslaved person named Roele in 1793 and £80 for an enslaved woman named Hannah and her child Bet in 1794.Footnote ¹⁰

One possible explanation for this occlusion might be that Jackson accepted Nancy as payment for legal services rendered, an idea floated by historian H.W. Brands. However, in such cases the relevant court tended to note that services were rendered and for how much. For example, on January 22, 1794, the Davidson County court recorded a “Receipt” written by Andrew Jackson to an individual named Moses Shelby for $3 “partial payment of legal fees” and on July 1, 1794, an individual named James Hannah wrote a bill of sale to Andrew Jackson for “livestock” in exchange for £21 and “legal services.”Footnote ¹¹

No mention of legal services accompanies Nancy's entry, leaving us to wonder what, precisely, he paid for her.

Jackson had little to his name in 1788, and what money he did possess was probably not enough to purchase a young woman in her prime, meaning that he may have acquired her through other means, perhaps illicit ones. At fifteen, for example, Jackson won the improbable sum of $200 in a dice game in Charleston. He then graduated to betting on horses and playing cards, eventually becoming known as one of the most “horse-racing, card-playing,” men in Salisbury, North Carolina. According to Robert Remini, Jackson came to rely on gambling so heavily that he would “surely have gone bankrupt” had he not regularly engaged in betting. Historian Hendrick Booraem concurs, noting that Jackson probably played “all fours” an English game that “was very popular on the old Southern frontier.” According to Booraem, “cheating was easy in all fours if one had some skill in handling cards,” which of course Jackson did. Jackson also enjoyed drinking and socializing, meaning that once he, John McNairy, and David Allison arrived in the small town of Jonesborough in the spring of 1788, it is not unreasonable to assume that they turned to cards in the evenings to pass the time.Footnote ¹²

Enter Micajah Crews. Though Crews is not mentioned again in Jackson's papers, there is evidence that such a person was born in South Carolina sometime around the same time that Jackson was, between 1765 and 1770, and it is possible that he was in Jonesborough at the same time as Jackson. There is also evidence that a Micajah “Crew” worked as a merchant out of Hanover, Virginia and may have done business in Jonesborough. Said Crew later got into trouble for taking advantage of customers who could not read. Perhaps he tried to fleece Andrew Jackson in a card game, only to be taken to the cleaners by the young rounder. Such an illicit exchange would explain how Jackson procured Nancy without spending any money, recording any price, or receiving a bill of sale.Footnote ¹³

We do not know. But we do know that Crews, or “Crew,” transferred Nancy to Jackson in an unconventional manner sometime before Jackson left for Nashville. We also know that almost immediately upon arriving in Nashville, Jackson sent word back to Jonesborough that he needed someone to go to court and swear under oath, on his behalf, that he, Jackson, had in fact purchased her.

Possession is nine-tenths of the law, but without possession one needs written proof of ownership. Bills of sale provided that, which might explain why Jackson had Allison rush to court. Nancy escaped. She could have left Jackson at any number of points along the Wilderness Road and returned to Jonesborough. Or she could have passed through Jonesborough and returned home, wherever that was. Or she could simply have disappeared into the forest.Footnote ¹⁴

Something similar happened to a settler named Boyd in the summer of 1784, four years earlier. Boyd journeyed with a small party from the Holston settlements north of Jonesborough to Nashville along the same route that Jackson took and, after two weeks of struggling up mountains, down valleys, and across rivers, lost an enslaved man named May near the Little Barren River, just north of modern-day Knoxville. Boyd and the other settlers had allowed May to wake up early and leave camp to search for food, but on June 29 they called for him and he did not return. When they searched their campsite, they learned that “May had taken his masters wallet & taken the other end of the road,” presumably going back.Footnote ¹⁵

Nancy could have done the same. Upon realizing that her new owner was a rambunctious card player with no money, no land, and no experience managing enslaved people, she might have seen an opportunity. She may have feigned servility to avoid being shackled, waited for an unsupervised moment, and then run. Three aspects of the Wilderness Road would have helped in this regard. First, there were no plantations or patrols nearby, and therefore no chance that a general hue and cry would be raised or that an advertisement or reward would help get her back. Second, the other settlers in the party were unlikely to care. Determined to reach Nashville, baggage-laden settlers had little interest in tracking runaways that did not belong to them. This misfortune befell Boyd four years earlier. When his enslaved person May left, the rest of the party moved on, leaving Boyd alone in the wilderness and vulnerable to the third factor helping Nancy: the Cherokee.Footnote ¹⁶

Long accustomed to hunting the western slopes of the Appalachians, the Cherokee controlled the territory between Jonesborough and Nashville, and they resented white settlement. This was particularly true of the Chickamauga, a subset of the Cherokee led by a warrior named Dragging Canoe. Dragging Canoe had thrown in his lot with the British during the American Revolution, and then proceeded to wage insurgent war against white settlers in the years following, from 1783 to 1788. He and his followers raided settlements, attacked forts, and haunted the Wilderness Road, killing settlers at random.Footnote ¹⁷

Settlers responded by traveling with armed guards and carrying guns themselves. This included Jackson, who carried two pistols in his saddle, one on his belt, and a rifle in his kit. He listened for signs that his group was being followed by Indians, and on one occasion warned his companions that a band of Cherokees was closing in, prompting them to break camp and escape. However, Jackson showed no sign that he was willing to leave the safety of the group, which included 60 settler families and an armed guard, to hunt for Nancy.Footnote ¹⁸

Of course, Nancy may have been afraid of the Cherokee too. The Chickamauga were not known for treating African Americans much better than whites, nor were they necessarily kinder to women. Some female settlers had been killed by Indians, others had been forced to marry Indian men, and Black women stood to be re-enslaved. The Cherokee tolerated slavery within their ranks and Nancy may have realized this.Footnote ¹⁹

However, Nancy may have gambled that an uncertain future with the Chickamauga was better than a life sentence with Jackson. Or perhaps she reasoned that she could outwit both Jackson and the Cherokee, making it to freedom in the North, refuge in the South, or—ironically—safety back in Jonesborough. So long as Jackson lacked a bill of sale, for example, he could not prove that he owned Nancy. Nor could anyone else, for that matter. She could have journeyed back to Jonesborough and then moved on to a place like Richmond, where she could have disappeared in the hustle and bustle of the city, holding herself out as a free woman and defying anyone to prove otherwise. This might explain why Jackson scrambled to concoct a bill of sale immediately upon reaching Nashville. And it might also explain why Nancy left when she did.Footnote ²⁰

But we can piece together a profile that might help us understand who she was, and what Jackson may have wanted from her. For example, Nancy might have been educated. Her decision to bolt after Jackson procured her without the proper documentation suggests that she might have known that he could not prove ownership without a bill of sale. This presumes some knowledge of the law, and maybe reading and writing as well. Literacy was rare among enslaved people at the time—states like South Carolina banned it—yet enslaved people who had close ties to whites could often skirt such rules. Such people were often the children of enslaved mothers and slave-owning fathers, raised in households where they picked up skills otherwise reserved only for white children.Footnote ²¹

Nancy may have been such a person. Take, for example, her name. Many slave-owners chose distinctive names for their enslaved people to “simplify the allocation of tasks and provisions,” as historian Cheryll Ann Cody notes. Such names tended to come from classical Greek and Roman literature, the Bible, or even African sources. First-generation enslaved people, for example, often chose African names for their children, names that established a link to the past and—also—met their owners’ demand for originality.Footnote ²²

Nancy was different. Hers was a popular name for both enslaved people and whites, making it the perfect bridge for someone of interracial ancestry. Perhaps the best-known example of this was Nancy “Nance” Hemings, the interracial daughter of white slave-owner John Wayles and enslaved Black woman Elizabeth Hemings, the mother of Sarah, or Sally Hemings, Thomas Jefferson's concubine.Footnote ²³

Nancy's story may have been similar. She too may have been the daughter of a white enslaver, and she too may have been educated and socially polished. This would have facilitated her escape, to be sure, and might also explain Jackson's interest in her. According to historian Edward Baptist, a separate market existed in the South for attractive, interracial women. Such women, sometimes called “fancy,” commanded extremely high prices and were sold expressly for sexual purposes. Nancy may have been such a person.Footnote ²⁴

However, two documents in the Washington County court record provide a clue. One is an arrest warrant. The other is a pre-trial detention order.

The arrest warrant is dated June 30, 1788 (four months before Jackson procured Nancy) and reveals that a member of the Washington County militia named Ninian Hoskins appeared before the court and accused a man named “Micagor Crews” of stealing two enslaved people and transporting them into the county. The judge, Richard White, cited Hoskins's statement as probable cause for issuing a hand-written warrant for Crews's arrest, affirming that “two Negroes” had been brought into the county, one “a fellow” and the other “a wench” who had been “stolen from somewhere the owner yet unknown” and brought into the district by Crews. One of the individuals was named “Jack” and the other was named “Nanci.”Footnote ²⁵

This must have been her. The spelling differed slightly, but how many other Nancys could there have been in Jonesborough in 1788? And how many could possibly have been owned by a man with a name that sounded nearly identical to “Micajah” Crews?

Probably none. However, the warrant does not reveal why Hoskins thought Crews was a thief, nor what evidence the Court gathered against him. All that remains, apart from the warrant, is a subsequent pre-trial detention order issued by Judge White, who found Hoskins's allegations plausible enough to order that Crews be temporarily detained. “On examination,” wrote White, “he appears guilty of said charge.”Footnote ²⁶

Why is it not clear. No details are mentioned, nor is there any subsequent record of Crews ever being convicted, which makes sense, since he transferred Nancy to Andrew Jackson four months later.

But the documents cast new light on Nancy's arrival in Jonesborough, nevertheless. Both suggest that something about Crews and Nancy was suspicious. It may be that Nancy struck onlookers as too “fancy,” i.e. too attractive and polished for someone like Crews to have purchased lawfully. Or Nancy may have told Ninian and White that she had been stolen. Historian Walter Johnson tells of such a person in New Orleans in 1857, an enslaved woman who was so light-skinned that she appeared European and pled with onlookers to free her.Footnote ²⁷

However, Nancy is not referred to in the court records as a white woman, or even a “mulatto”—a common term used to describe interracial people at the time—but rather, a “negro” woman. Of course, such a woman may still have been interracial and/or may still have told onlookers that she had been stolen. Assume, for example, that Crews had acquired Nancy legally, but promised not to transport her far from home. Historian Jenny Wahl has found cases where sellers made such contractual agreements with buyers, offering discounts if the buyer agreed not to transport the enslaved person too far from family and friends. Had Crews signed such an agreement to get Nancy at a discount but then carted her to Jonesborough to turn a profit, she may have told bystanders that she was stolen precisely so that Crews would be hauled into court and forced to adhere to his original, contractual agreement. That presumes Nancy possessed some knowledge of the law, of course, but it also explains how Crews might have been detained and then released. According to Wahl, southern courts tended to award damages rather than insist on specific performance, which means that Crews may have been able to secure his release by simply paying Nancy's prior owner more money.Footnote ²⁸

Another possibility, perhaps equally plausible given Nancy's subsequent disappearance, is that she had run away from her past owner, and Crews had caught her. Southern newspapers at the time ran regular advertisements about escaped slaves, often posting rewards for anyone who might apprehend them. For example, an enslaver named Abraham Marshall posted an ad in the Augusta Georgia State Gazette on June 14, 1788, only two weeks before Crews was arrested for stealing Nancy, claiming that a “negro fellow” named Jack had escaped his plantation on Kiokee Creek, near the Georgia/South Carolina border. “A handsome reward will be paid,” noted Marshall, “to any person who will apprehend and deliver the said fellow, named Jack, to me at my plantation on the Kiokies [sic], besides all reasonable expenses.” This might explain what Crews was doing with Nancy and Jack. He had captured them and was in the process of returning them to their owner when he was arrested.Footnote ²⁹

But if this was the case, why—or rather how—did Crews then transfer Nancy to Jackson, four months later? And, furthermore, what was he doing in Jonesborough? The warrant for Crews's arrest states specifically that he had transported Nancy and Jack into Washington County, where Jonesborough lay, which is odd since there were few, if any, plantations there. Most plantations lay on the opposite side of the Appalachian Mountains, near the coast, and it seems strange that Crews would be transporting Nancy and Jack to the frontier if, in fact, he was hoping to return them to their owner for a reward.Footnote ³⁰

Maybe Crews was headed to the frontier for another reason. Maybe he had agreed contractually to transport Nancy and Jack as far from their owner as he possibly could. While many enslavers had no qualms about employing physical violence to discipline recalcitrant slaves, others preferred to sell enslaved people who refused to cooperate, provided the buyer agreed to remove them as far away as possible. Thomas Jefferson did this in 1803, requesting that Thomas Mann Randolph sell a violent slave to traders from Georgia, precisely so that he would never be heard of again. “There are generally negro purchasers from Georgia passing about the state,” wrote Jefferson, “to one of whom I would rather he [slave Cary] should be sold than to any other person. I should regard price but little in comparison with so distant an exile of him as to cut him off compleatly [sic] from ever again being heard of.” The slave in question, Cary, had struck another enslaved man in the head with a hammer, convincing Jefferson that “an example” needed to be made of him.Footnote ³¹

Two aspects of Jefferson's disciplinary approach might shed light on Nancy's plight. One, it might explain why Crews transported Nancy to Jonesborough, a jumping off point for settlers heading to the remote outposts of Nashville, Boonesborough, and Louisville. Two, it might also explain why Ninian Hawkins suspected that she was stolen. If, for example, Crews had purchased Nancy because she was recalcitrant, then there is a good chance that he paid a discounted price, meaning he could have paid a small sum for a woman so “fancy” that onlookers—including judge Richard White—suspected he had stolen her. Historian Robert William Fogel argues that enslaved people who were known for being rebellious, including runaways, “sold for average discounts of up to 65 percent,” a point that Thomas Jefferson himself seemed to confirm when he told Thomas Mann Randolph that price was irrelevant so long as “Cary” was never seen or heard from again.Footnote ³²

If Crews had made a deal with Nancy's owner to transport her beyond the pale in exchange for a discounted price, then a few assorted pieces of her puzzle might fall into place. One, such a deal helps to explain why Crews took Nancy to Jonesborough, a frontier town far from Richmond, Williamsburg, and Charleston. Two, it also helps to explain why Hawkins and White suspected Nancy of having been stolen, she looked too expensive for a low-rent trader to possess. Three, the idea that Crews bought Nancy at a discounted price helps to explain why Crews was not ultimately convicted of stealing her, for all he had to do was convince a judge that he had purchased Nancy for less than she might have appeared to be worth precisely because she was refractory, something that he could have done by requesting a letter from her prior owner. Such a resolution would not have required a trial, which explains why there is no trial transcript, sentencing order, or other document suggesting a trial was ever held. Had Crews been accused of breaching a contract, by contrast, then there probably would have been some type of judicial proceeding involving Nancy's prior owner.

Regardless, the allegations of theft against Crews corroborate the idea that Nancy absconded from Jackson. Either she left to return to her family (and her former owner), or she left because she had already escaped once, and had no qualms about running again.Footnote ³³

Both possibilities point to escape, and that gives us another reason for why Jackson might have wanted a bill of sale. Not only did it establish ownership in the event Nancy was caught, but a bill of sale also enabled Jackson to sue Crews for breach of warranty. According to Ariela Gross, such suits were common in the South and could be brought even if buyers did not have a written document. They could base their claims simply on verbal promises that sellers had made them. “When sellers sold slaves without an express warranty,” notes Gross, “buyers wondered why.” Gross and Wahl have both found buyers who sued sellers for failing to disclose an enslaved person's problems, including their proclivity for running away. Many slave sales, they maintain, carried with them a warranty of “good character” that included a presumption the enslaved person in question would not abscond at the first opportunity.Footnote ³⁴

However, Jackson's bill of sale did not mention a price, which raises questions about how successful a suit for breach of warranty could have been. Had Jackson paid a hefty sum for Nancy, then he would have been more likely to recover damages in court. Had Jackson paid nothing, on the other hand, then he would have lacked any ground for a breach of warranty claim.

Which leads us to a final reason for why Jackson might have procured a bill of sale for Nancy.

While we might like to believe that Nancy ran from Jackson and came to a better place, it would be naïve to ignore the possibility that she may have met her death. After all, there is no evidence that Jackson ever filed a breach of warranty suit against Crews, nor is there any evidence that Jackson posted an ad announcing a runaway. By contrast, Jackson pursued an enslaved man that ran away from him in 1805 “for years,” as J.M. Opal notes, “sending letters to friends and officials alike” hoping to recover him. And Jackson posted a frightening ad for another runaway slave in 1804, promising to pay $50 for anyone who captured him, plus $10 “for every hundred lashes any person will give him, to the amount of three hundred.”Footnote ³⁵

Assume, for example, that Nancy tried to run but Jackson caught her. He may have struck her, and she may have struck him back, sending him into a murderous rage. Or Nancy may have drawn one of Jackson's knives on him, or threatened him with one of his guns, prompting him to take her life in self-defense.

Or, assume that Jackson acquired Nancy for the very reasons that Mark Cheathem and Dawn Peterson surmise—sexual gratification—but Nancy resisted. According to historian Peter Bardaglio, southern slaveowners “often approached female slaves expecting sexual favors” and when they “encountered opposition to their request, many resorted to outright force to achieve their purpose.” However, not all enslaved women succumbed to such attacks. According to historian Wilma King, “some slaves resorted to violence to protect themselves and loved ones from abuse,” and “to protest the sexual aggression heaped upon them.” One enslaved woman in Missouri named Celia “choked, suffocated, and burned” her owner to death after he tried to force himself on her.Footnote ³⁶

What would Jackson have done if Nancy fought him? He became known later in life for violent outbursts, so is it not possible that he became violent when a woman that he thought had to submit to him refused? Or, what if—in refusing him—Nancy also fought back physically, maybe even getting the better of him? How would Jackson have responded to that?

If Jackson did in fact hurt or kill Nancy, it would explain why he never mentioned her again and it might also explain why he decided to procure a bill of sale immediately upon arriving in Nashville. Such a document could serve as an insurance policy against criminal prosecution. If Nancy had been Jackson's property, for example, then it is less likely he would have been investigated, much less prosecuted for rape, assault, or even murder. By contrast, if Nancy had been a free woman, then it is more likely he could have been charged. Not much more likely, to be sure, but Jackson's friend John McNairy may have advised him to hedge his bets. McNairy was the appointed judge for Davidson County and may have felt that Jackson—as his state's attorney—needed to burnish his reputation in the event rumors about Nancy started to swirl.Footnote ³⁸

Of course, someone would have had to report him, but there were 100 odd people in Jackson's Wilderness Road party, and some may have wondered what exactly Jackson was doing with, and to Nancy. Jackson himself may have felt like he needed a legal fig leaf in the event someone talked, for fear he would end up being reported—like “Micagor” Crews was reported by Ninian Hoskins to Judge Richard White.

However, something appears to have happened to Nancy between Jonesborough and Nashville. Either she absconded or she died. And this was not something Jackson had expected or hoped might happen. Whatever he thought he had gained in Jonesborough, he lost.

One, Jackson's interaction with Nancy during a formative phase of his career as a southern enslaver may have shaped the way that he came to view slavery generally. For example, it may have alerted him to the realities of slave resistance and—specifically—to the dangers involved in transporting people into the wilderness. Whether Nancy ran, fought, or both, she obviously did not comply with Jackson's wishes, and may have led him to reassess his own ideas about what he could do to enslaved people and—conversely—what they could do to him.

Which leads to a second conclusion. Nancy's defiance might explain why Jackson never sexually exploited another female slave. Unlike Thomas Jefferson, Jackson never took an enslaved concubine, sired enslaved children, or partook in what legal historian Adrienne Davis calls the “sexual political economy” of American slavery. According to Davis, “slavery's legal and cultural institutions systematically made enslaved women's reproductive and sexual capacity available to serve any number of political and economic interests of elite white men.” Annette Gordon-Reed agrees, noting that even though “the pervasive doctrine of white supremacy supposedly inoculated whites against the will to interracial mixing,” that “doctrine proved to be unreliable when matched against the force of human sexuality.”Footnote ³⁹

Early stories of him as a young man suggest that he was hardly a prude. He spent his teenage years gambling, drinking, and frequenting houses of ill-repute. Whether he slept with prostitutes or not is unclear, but we do know that he socialized with them. For example, one apocryphal story about Jackson maintains that he invited two prostitutes to a formal ball in Salisbury, North Carolina when he was a law student, to the horror of the local elite. He also courted and married a woman who was betrothed to someone else.Footnote ⁴⁰

Maybe it was Nancy. Perhaps she taught Jackson that forcing oneself onto an enslaved person was dangerous, both for the slave and for the enslaver. While historians like Edward Baptist argue that “slavery permitted unchecked dominance and promised unlimited fulfillment of unrestrained desire,” maybe it did not. Maybe dominance, in some cases, could be checked, depending on who the enslaved person was, and what they were willing to do.Footnote ⁴¹

This yields a third conclusion. Jackson's negative experience with Nancy may have instilled in him an aversion to interracial sex generally. More than any other president before him, Jackson embraced the idea of strict racial separation, a social order in which whites were free, Blacks were enslaved, and Native Americans removed. He came to view interracial people, or what he called “half-breeds,” as threats to the American order; and he waged a vicious campaign against an interracial coalition of Native Americans, African Americans, and Europeans in Florida, a place that he likened to “Babylon.”Footnote ⁴²

Maybe Nancy had something to do with this. As the first enslaved person that he owned, she may have left a greater impression on him than subsequent acquisitions, and she may have sharpened his racial views in a way that distinguished him from other prominent enslavers of his time. According to Annette Gordon-Reed, for example, most white southern men did not care that interracial intimacy could, and did, blur what Daniel Sharfstein has called the “invisible line” between Black and white, thereby undermining the legal basis for slavery. After all, if enough slave-owners fathered children with enslaved women, then eventually there would be no clear delineation between the races, and no clear explanation for who was to be enslaved and who was to be free.Footnote ⁴³

America's ambassador to Spain, a man named William Short, advocated precisely such a process in 1798, to end slavery. As Gordon-Reed recounts, Short wrote Thomas Jefferson telling him that “intermixture between the races offered the best possible solution to America's racial predicament,” a point that Jefferson seemed reluctant to admit. For him, and for Jackson, slavery underpinned the American economy. However, Jefferson sired children with an enslaved woman, thereby undermining the very system he relied on, and Jackson did not. For some reason, Jackson defied the stereotype of the depraved southern slave-owner and became a staunch proponent of reinforcing racial categories.Footnote ⁴⁴ Nancy was not the only factor contributing to this, to be sure, but Jackson's experience with her might have started him down the road of reflection on a larger problem, namely the opportunities that westward expansion opened for the enslaved. The farther white enslavers pushed into Indian territory, in other words, the more chances there were for enslaved people to escape and fight back. This was certainly true of the Wilderness Road, where there was little to prevent an enslaved person from walking off into the woods, but it may have been true of the frontier generally, which Jackson witnessed first-hand for much of his early life.

Unlike Jefferson, in other words, who looked at the west as a “boisterous sea of liberty,” Jackson may have spied treacherous waters. As J.M. Opal notes, “because their households were in constant danger,” Jackson and his fellow settlers “lived in emergency rather than ordinary time,” their remote homesteads “‘a scene of slaughtered innocence’” rather than domestic bliss. And as Andrew Burstein notes, “men of the frontier felt the need to assert their strengths, indulge in profanity, and behave violently in order to conquer or deny their fears of the wilderness condition.”Footnote ⁴⁵

Alan Taylor has shown convincingly that fear haunted white Americans during the early days of the Republic, particularly “southern men who dreaded Indians on the frontier and slave revolts on their plantations.” Jackson faced both at once, and adopted a “vengeful style” in response, an aggressive posture that “thrilled southern men” but may have belied a deeper insecurity.Footnote ⁴⁷

J.M. Opal argues, for example, that Jackson regularly invoked gender in his various campaigns against Native Americans and Black people, arguing that white women needed to be protected from nonwhite aggressors. “The assassins of women and children must be punished,” he declared after Red Stick Creeks attacked a fort in Alabama in 1813. Nicole Eustace shows that Jackson made a similar case against the British in New Orleans, arguing that they too needed to be stopped before they assaulted American women. “[H]ave you a wife or daughter?” he asked, hoping to rally his men by conjuring the image of Redcoats raping their loved ones.Footnote ⁴⁸

According to Laurel Clark Shire, such “depredation accounts” were common in the nineteenth century, and often emphasized “female passivity, piety, maternity, and domesticity.” But what of Jackson's interaction with Nancy? Did her rejection of him somehow fuel his need for revenge? Or did her disappearance absolve him of the guilt that other white enslavers bore for betraying their white wives and exploiting their Black servants? Did Nancy somehow castrate Jackson by leaving him, fighting him, or both—before he had a chance to rape her?Footnote ⁴⁹

But if Nancy did influence Andrew Jackson in some way, then maybe she deserves a place in the long litany of enslaved people who fought back against slavery and shaped American history in the process.