This article is part of a series about Andrew Jackson
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Andrew Jackson (lived, 1767–1845; U.S. presidency, 1829–1837) bought and sold slaves from 1788 until 1844, both for use on his plantations and for short-term gain through slave arbitrage. He was most active in the interregional slave trade, which he termed "the mercantile transactions," from the 1790s through the 1810s. Available evidence shows that speculator Jackson trafficked people between his hometown of Nashville, Tennessee, and the slave markets of the lower Mississippi River valley.

Jackson bought and sold outright, but slaves also served as barter for trade goods, currency for real estate transactions, and as stakes in gambling on horse races. While Jackson had a number of business interests in Tennessee, many of Jackson's slave sales took place in the Natchez District, Feliciana District, and in New Orleans. Jackson is believed to have had a stand in the vicinity of Bruinsburg, Mississippi (not far from Port Gibson), and/or at Old Greenville, now-extinct settlements at the southern end of an ancient and rugged Indigenous trade route known to history as the Natchez Trace. Jackson's customers included his wife's sister's extended family and their neighbors who owned tobacco farms and cotton plantations worked by slave labor. After 1800, Jackson often tasked his business partner and nephew-by-marriage John Hutchings with escorting their shipments to the lower country.

In 1812, while arguing over a coffle that he himself had shopped around Natchez, Andrew Jackson admitted in writing that he was an experienced slave trader, stating that his cost for "Negroes sent to markett [sic]...never averaged more from here than fifteen dollars a head." In addition to the substantial evidence of slaving to be found in his letters, Jackson was identified as a slave trader in his own lifetime by abolitionist writers including Benjamin F. Lundy and Theodore Dwight Weld, and there are a number of secondhand accounts attesting to Jackson's business interests in the "lower country." Jackson's slave trading was a campaign issue during the 1828 United States presidential election. Some of Jackson's accusers during the 1828 campaign had known him for decades, and were themselves affiliated with the trade. His candidacy was also opposed by a number of Natchez elites who provided affidavits and/or copies of Jackson's slave-sale receipts to local newspapers. Jackson denied the charges, and the issue failed to connect with the electorate.

Little is known about the people Jackson sold south. However, because of the partisan hostility of the 1828 campaign, there are surviving records naming eight individuals carried to Mississippi: Candis, age 20, and Malinda, age 14 ($1000); Fanny ($280); a 35-year-old woman named Betty and her 15-year-old daughter Hannah ($550); and a young mother named Kessiah, and her two children, a three-year-old named Ruben and an infant named Elsey ($650).

Jackson, a native of the Carolinas and pioneer settler of Tennessee in 1788, was connected to colonial-era Mississippi by the geography of commerce. Moving goods between the east coast and the Cumberland River basin was challenging because of the necessary, difficult, and expensive passage through the Appalachian Mountains.^[1] Moving goods north to market in Kentucky or the Illinois Country was pointless because those places produced more or less the same products as Tennessee.^[2] That left the western inland waterways as the road to market, and in much of what became the territory of the United States in North America, these waters lead to the mouth of the Mississippi River at the Gulf of Mexico and from there to the rest of the Atlantic world.

After the bloody Natchez revolt in 1729, counterrevolutionary violence by French colonial militias all but destroyed the Natchez people. Most of the Natchez were killed, some were sold into slavery on Saint-Domingue, a few survivors were assimilated into the Muscogee and Cherokee nations.^[3] In 1765, the Choctaw signed the old Natchez domain over to Great Britain, and as part of British West Florida, the Natchez District attracted a handful of families leaving the Thirteen Colonies during the American Revolutionary War.^[a] In 1785, a visitor estimated the population of the Natchez District at 2,000, with approximately 900 slaves laboring for 1,100 white settlers.^[6] Spain took control and opened Spanish West Florida to American colonists on August 23, 1787.^[7] The population of colonial-era Natchez was clustered along the waterways (which also served as the region's commercial thoroughfares),^[8] namely the Big Black River, Bayou Pierre, Cole's Creek, Fairchild's Creek, St. Catherine's Creek, and the Homochitto River, with its right-bank tributaries Second Creek and Sandy Creek.^[9] Just about everything else between the Mississippi River and Georgia was titled to the Cherokee, Chickasaw, Choctaw, and Muscogee people native to the region.^[9] By the last decade of the 18th century, the Natchez region had a polyglot, pluralistic, creolized culture,^[10] with a changing economy, as tobacco and indigo (and timber and cattle) were being supplanted by industrial-scale cotton agriculture.^[11] There are no known sources that historians can use to study the importation of slaves to Mississippi prior to the 1810s, but it is clear that the end of the Spanish tobacco subsidy and the simultaneous removal of trade barriers spurred an increase in the slave trade.^[12]

The primacy of cotton meant that "slavery became very much a central institution and defining feature" of the region.^[13] Circa 1792, settlers were predominantly Anglo-American and two out of every three slaves in the Natchez District were African-born.^[14] Slaves from overseas were often re-exported through the West Indies, particularly British colonial Jamaica,^[15] whose planters preferred to buy Igbo, Yakö, and Yoruba people "from the Gold Coast and the Bight of Benin."^[16] The Mississippi Territory of the United States was organized in 1798.^[7] When the Natchez District transitioned from Spanish to American suzerainty and from "a frontier to a borderland, and eventually to a bordered land...slaves were the losing party in the transfer of power."^[17] Although the territorial organizing act prohibited the introduction to Mississippi of slaves from outside the U.S., this "foreign trade ban seems to have been ignored."^[18] The importation of these so-called "saltwater slaves" to U.S. ports continued until 1808, when the law prohibiting transatlantic slave shipments went into effect.^[19] Available evidence shows that Jackson participated in what is called the internal slave trade, buying and selling enslaved Americans, born and raised in the first 16 U.S. states, who were termed "country-born negroes" (contra enslaved Louisiana Creole people, "Guinea negroes", or "Congo born" slaves, perhaps bearing the "marks of their country"). Jackson moved people from the upper South to the Deep South, where more demand made for higher prices.^[20] As of 1800, the total estimated population of the Natchez District was a little under 4,700 people, about evenly split between free white people and enslaved black people.^[21] Meanwhile, Indians resident in the greater Mississippi delta found that their British and Spanish alliances had collapsed as a consequence of the American Revolution and they could no longer effectively inhibit the growth of the plantation regime.^[22] This left the theft of horses and mules, and the capture or protection of fugitive slaves, as the few means available for the western division of the Choctaw to disrupt colonization in and around Natchez without engaging in widespread violence, inviting outright war with the Americans.^[23] Interested governments did not attempt to enumerate Indigenous people in the vicinity of Natchez, but there were likely 30,000 Native Americans resident in the unceded lands between the river and the Georgia frontier.^[21][24]

In 1802, Thomas Jefferson wrote Robert R. Livingston that the preeminent geopolitical enemy of the United States was whichever power was the possessor of New Orleans "through which the produce of three eighths of our territory must pass to market, and from it's fertility it will ere long yield more than half of our whole produce and contain more than half our inhabitants."^[26] The following year, France sold the 828,000 sq mi (2,140,000 km²) Louisiana territory to the United States.^[27] A few months later Jefferson wrote Jackson:

"The acquisition of Louisiana is of immense importance to our future tranquility insomuch as it removes the intrigues of foreign nations to a distance from which they can no longer produce disturbance between the Indians & us. it will also open an asylum for these unhappy people, in a country which may suit their habits of life better than what they now occupy, which perhaps they will be willing to exchange with us: and to our posterity it opens a noble prospect of provision for ages. the world will here see such an extent of country under a free and moderate government as it has never yet seen."^[28]

As Jackson himself purportedly argued in 1812, if the mouth of the Mississippi were closed to Americans "all the fruits of his industry rots upon his land—open, and he carries on a trade with all the nations of the earth. To the people of Western Country is then peculiarly committed by nature herself the defense of the lower Mississippi and the city of New Orleans."^[29] Louisiana became the 18th U.S. state on April 30, 1812.^[30] Mississippi was admitted to the Union as the 20th state on December 10, 1817.^[31]

Jackson spent very few of his formative years anywhere near the center of national politics, and so the ways he behaved as president only make sense in the context of what preceded. His decisions are best understood in light of a bitter and hard-fought experience. To say that he was prosecutor, state judge, congressman, and U.S. senator—all before he rose in stature as a victorious major general during the War of 1812—is to explain little or nothing about Jackson's appeal or even his ambition.

— The Passions of Andrew Jackson by Andrew Burstein (2003)^[32]

Jackson's attitude toward Texas fit with his foreign policy in general, which was largely a projection of his personal experience. As a planter and land speculator, he took an interest in the expansion of cotton acreage and in securing overseas markets for agricultural staples. Indian Removal, foreign trade agreements, and Texas annexation all reflected these interests. A soldier renowned for his defense of New Orleans, he remained concerned with the strategic security of the Southwest and now wanted the border pushed far beyond the Sabine...[Late in life] Jackson had removed any cloak from his aggressive imperialism...the letters he scratched out breathed fire against old enemies, the British and the abolitionists who stood in his way.

— What Hath God Wrought: The Transformation of America, 1815–1848 by Daniel Walker Howe (2007)^[33]

During his first months living in the Watauga District near the present-day border between North Carolina and Tennessee, in "summer or early fall 1788," Jackson organized and publicized a half-mile race at the semicircular Greasy Cove racetrack at what is now Erwin, Unicoi County, pitting his racehorse against one fielded by Col. Robert Love, Jackson's acquaintance of four years past and a veteran of battles with the Cherokee, the Shawnee, and the British.^[34] The planned match triggered an absolute frenzy of wagering: "Guns, furs, iron, clothing, cattle, horses, negroes, crops, lands and all the money procurable were staked on the result."^[35][36] Jackson personally rode in the race and reacted to his defeat with a "Vesuvius of rage," during which display "Jackson denounced the Loves as a 'band of land pirates,' because they held the ownership of nearly all the choice lands in that section."^[35] Shortly thereafter, on November 17, 1788, in Washington County, Jackson made his first recorded slave purchase, a woman named Nancy who was between 18 and 20 years old.^[37][38] According to historian Whitney Snow, Jackson's employment income as an attorney was unpredictable and insufficient to cover his financial losses, so he "began dabbling in mercantilism, land speculation, and the interstate slave trade" and found that of the three, "slave trading not only relieved Jackson of debt but also allowed him to accumulate a larger-than-average work force of slave labor, a sure sign of status at the time."^[39][b] The debts accumulated because Jackson was prone to making imprudent financial investments (such as a disastrous deal with fellow land speculator David Allison), and extravagant wagers on sporting events.^[44][45] As a case in point, in 1815 a large friend saw fit to pick up General Jackson and carry him away, in order to prevent him from betting US$10,000 (equivalent to $166,473 in 2023) that his horse Yellow Queen would win her race against Haynie's Maria.^[45] (Jackson's Yellow Queen lost the race against Haynie's Maria.)^[45]

Regarding the accumulation of slaves, as Frederick M. Binder put it in his The Color Problem in Early National America (1968), "There was much about [Jackson] to remind one of the rude frontiersman, but one need only read his letters concerning family affairs and plantation management to recognize marks of the Southern aristocrat."^[47] Yet, according to a study of agriculture in Tennessee by Harriette Simpson Arnow, "Jackson's letters in particular are relatively untouched with remarks on the nature of the soil about him, the weather, and the swing of the crops through the seasons...farming was for Andrew Jackson...a capitalistic enterprise in which he invested, not himself, but only money."^[48] The biographer of Joseph Erwin, who was, like Jackson, an interstate slave trader and Nashville racehorse owner, wrote of her subject: "Absurd as it now seems...planters of that early period considered large capital tied up in slaves the best of investments, the most desirable property for a remunerative income...lands were a secondary consideration."^[49]

In pursuit of income if not fortune, merchant and slave trader Jackson used a flatboat to get from Stone's River to the Cumberland River (or from the Watauga to the Holston to the Tennessee) to the Ohio River, to the Mississippi, and thence south to the Natchez slave market in Spanish West Florida and/or the colonial-era New Orleans slave market in Louisiana. Lacking steamboats, which had not yet been invented, Jackson and companions made the return trip on foot (slaves) or horseback (traders) by the Natchez Trace, an ancient track through the hundreds of miles of Chickasaw and Choctaw territory between the northern fork of Bayou Pierre and the Tennessee River, ending at Jackson's farm, originally Poplar Grove, then Hunter's Hill, and after 1804, The Hermitage. There is no record of Jackson owning land or operating a plantation of his own on Bayou Pierre.^[50][51][52]

Historian J. Winston Coleman wrote that at the turn of the 19th century, "Tennessee was as wild and rough a frontier country as the Nation possessed. Life in those parts was both hard and turbulent, and a short one for many a man who tried to get on for himself in that fast-growing section of young America. Reckless gambling, hard drinking, and fighting to the death with pistol and knife were the order of the day. Men fought for their rights and for their lives...cut-throats of every description defied the laws of the back country districts, and the towns themselves were scarcely less barbarous."^[53] The exact site where the Mississippi store(s) stood has been lost, but it was one of several such outlets for Jackson's business endeavors, all at a time when "Money was scarce, and the interchange of goods was difficult and hazardous. Barter was still commonly employed in conducting commercial transactions."^[54] According to the editors of The Papers of Andrew Jackson, "Between 1795 and 1807 Jackson followed general-store merchandising at least as fully as farming, the law, or the military."^[55] Goods from Philadelphia resold in the Cumberland were marked up triple.^[56] Cotton purchased by middlemen in the Cumberland resold for double in New Orleans.^[57] Products for sale include fabric, "salt, grindstones, hardware, gunpowder, cow bells, and whatever else the people of the neighborhood wanted. In payment for these commodities, they took, not money, but cotton, ginned and unginned, wheat, corn, tobacco, pork, skins, furs, and, indeed, all the produce of the country."^[56] Middle Tennessee had originally produced mostly corn and stock animals, but by 1800 cotton had become so lucrative a cash crop that cotton bales served as a local currency.^[58] The "produce of the country" that was traded included slaves. In 1805, Jackson and his nephew accepted $25 in cash and "A Negro Woman namd. Fan a bout forty five years of age" to pay off the $150 past-due account of Andrew Steele at their store.^[59]

Jackson's commercial hub in Tennessee was at Clover Bottom, which was being developed as a plantation when "men from nearby places, Jackson included, formed a jockey club early in the nineteenth century and laid out a racecourse here."^[60] In 1805 Jackson oversaw construction at Clover Bottom of a racetrack and horse stables, viewing stands, "a tavern or lodging facility," a store, and "booths for hucksters."^[60][61][62] There was gambling going on in this establishment, as well as throughout the settlement.^[63][64] (According to court records, popular hobbies in the Cumberland included a card game called loo, another game called fives, and the crime "assault and battery.")^[65] Jackson also ran saloons in Tennessee. On August 19, 1806, Cage & Black made a rental agreement with Andrew Jackson and James S. Rawlings for a house, lot, and stables in Gallatin, Tennessee.^[66] Rawlings was married to a niece of Rachel Jackson.^[66] On September 13, 1806, Rawlings advertised that he had opened a tavern in Gallatin that offered "a well-chosen assortment of imported spirits and wines."^[67] This brick-built Gallatin stable was probably where Jackson lost $500 to Edward Ward, president of the Clover Bottom Jockey Club, in a bet on a fight between gaffed cocks.^[68] The bet was for gold, and Jackson apparently tried to avoid the payout by working the refs.^[68]

The Clover Bottom store was also where Jackson's company built and sold flatboats to other travelers going downriver. River-traffic statistics involving flatboats illustrate how early Jackson came to Mississippi, and thus how closely he must have been involved in its colonization. According to writer David O. Stewart, in 1792 "only a dozen flatboats made the journey downriver to New Orleans," but by 1802, it was more than 500, and by 1807, the count was closer to 2,000 a year.^[69] According to another account, in 1790, 64 flatboats docked at Natchez the entire year, while on a single day in 1808 a visitor counted 150 flatboats tied up at the Natchez landing.^[70] There is a surviving contract between a riverman and Jackson's partner John Coffee arranging for a flatboat to depart from Haysborough, Tennessee for New Orleans in 1803 loaded with 25 bales of cotton and 77 hogs, which offers some sense of the scale of Jackson's shipments.^[71] In 1803 his firm built boats "for the war department in expectation of difficulty with Spain in Louisiana,"^[72] and in the course of the 1806–07 expedition that came to be known as the Burr conspiracy, Aaron Burr ordered five of Jackson's boats, picked up two that were ready at Clover Bottom, and set off for the south from Jackson's landing at Stones River, weeks later surrendering himself to authorities at Peter Bruin's house at Bruinsburg.^[73][74] These boats were themselves valuable in the lower Mississippi, which had a shortage of planed lumber.^[75][76][c] The Clover Bottom store, where Jackson built and sold flatboats, raced horses, and took people as a form of payment, was "a two-story building near today's Downeymead Drive."^[80]

Jackson's mercantile enterprises and gaming operations appear to have been entangled with his slave-trading, real estate speculation, and his imperial designs on Indigenous lands, which was the case throughout pioneer-era Tennessee, whose leaders, colonels, legislators, and "land-grabbers" were men whose "classifications...greatly overlapped."^[81] As Nashville historian Anita S. Goodstein put it, "Land speculators, merchants, self-made lawyers—all dealt in slaves. Indeed they used slaves almost as currency."^[82] Historian Chase C. Mooney, in his 1957 Slavery in Tennessee, came to the conclusion that John Overton, Jackson's business associate and political patron,^[83] "might be classed as a slave trader—but not of the coffle-driving type—for he both purchased and sold quite a number of Negroes. Some of his purchases follow: Robin and Pol, $530; Sam, Phyllis, and Ezekiel, $1050; Mathew and wife (slaves of John Coffee, purchased through the United States marshal), $710; Charles, $180 in 'horse flesh, and one hundred and ten dollars in notes'; Lewis, $400; Betty, $800; Elijah, $450; Wood, $600; Bob, $500; Huldy, $375; Tom, $300; Ben, $385; Arthur, $315; Washington, $340; Adam, $500; Martin and Oliver, $365; and 'two negroes,' $700.28."^[84] In 1819, Overton asked Jackson to have John Brahan of Huntsville, Alabama repay him for a debt of approximately $800 in "one or two likely healthy boys of 12 or 13 years of age at such price as you may think they are worth in Cash, and as you would trade for yourself."^[85] Another example of the use of slaves to repay debts is Stockley Donelson's 1791 offer to pay off Jackson with "one likely Country born Negro boy or girl."^[86] According to Goodstein's analysis of 452 Nashville-area transactions involving approximately 700 enslaved blacks in the period from 1783 to 1804, "The overwhelming number of sales were of a single slave, man or woman or child. Of the 452 transactions only 116 involved transfers of more than one slave...Almost half of those for whom we have age data were under 16. It was not uncommon for children to be sold separately, away from parents or friends. Witness Aron, age six, sold to Andrew Jackson in 1791."^[87] Jackson paid £100 to buy Aron from George Augustus Sugg on December 21, 1791.^[88] He was not resold but grew up at the Hermitage where he worked as the plantation blacksmith and had a wife and three children as of 1825.^[89] If the Hermitage kept to the pattern found elsewhere in the south, Aron's work tasks would have included shoeing horses, making nails, repairing metalwork, forging chains, and locking shackles and collars on other slaves, which was called "ironing negroes."^[90][91]

Slavery has made labor dishonorable to the white man; and, as they must have means of living, they generally resort to gambling for support.

— Narrative of Henry Watson, A Fugitive Slave (1848)^[92]

That is the quintessence of the slave doctrine; labor degraded, the laborer degraded, money exalted, and the owner of property exalted.

— John Bolles, Boston Semi-Weekly Republican, September 9, 1848, via Arthur M. Schlesinger Jr.'s The Age of Jackson (1945)^[93]

[Land speculators] made this [Jeffersonian] yeoman ideal itself into a basis for financial wizardry, conjuring up supposed fortunes through little apparent labor at all.

— Michael A. Blaakman, Speculation Nation: Land Mania in the Revolutionary American Republic (2023)^[94]

In 1781, at age 14, Andrew Jackson found himself unattached, his immigrant parents and two older brothers all having died of disease or misadventure over the course of his childhood.^[95] As such, he inherited "four or five hundred pounds sterling" when a grandfather died in Ireland.^[96][97] He visited Charleston to pick up the bequest (presumably paid out in the form of South Carolina pounds), and there he drank and gambled away his accrued net worth.^[98] He moved to North Carolina, he studied law, and then, in company with work friends, he moved west to examine the prospects for a frontier lawyer in the new settlement that was being hacked out of the woodlands along the Cumberland River in the Mero District of North Carolina, shortly to become the Territory South of the River Ohio.^[98] Jackson was thus 22 years old in 1789, when he rode the waters of the Mississippi south to Bruinsburg, which was located at the confluence of the Mississippi and Bayou Pierre at what was at that time the northernmost White settlement in the Natchez District. The name Bayou Pierre dates to the French period, but the local pronunciation of bayou "ignores the y and rhymes the word with now."^[99] In 1789 there were no riverfront settlements between L'Anse à la Graisse (later known as New Madrid, Missouri) and Bayou Pierre.^[100] The settlement had no public buildings; a church would not be built for another decade.^[101][102] White families resident on Bayou Pierre and the Big Black at that time lived in small nuclear-family households, and if they owned slaves the count was in the single digits.^[103] The earliest surviving description of Bruinsburg dates to March 25, 1801: "...pass't Judge Bruin's at the lower side of a creek called Biopere...some Houses but no improvements worth notice..."^[104] The fullest description of life on pre-territorial Bayou Pierre comes from the autobiography of Confederate general and Reconstruction-era Mississippi governor Benjamin G. Humphreys, recapitulating the memories and legends of three generations of his family:^[105]

"In 1793 my father and mother moved from Grind Stone Ford to a tract of land on the north side of the Big Bayou Pierre known as the 'Hermitage' held by my mother by grant from the Spanish Government. At this time, what is now known as Claiborne County, was an unbroken wilderness tenanted only by about five white families, a few vagabond Spaniards, strolling Choctaw Indians, the bear, the panther, the catamount, the wolf, and the deer. A horse path leading from Natchez, through what were afterwards known as Washington, Seltsertown, Union Town, Port Gibson, Grind Stone Ford, Rocky Springs to Cayuga in the Choctaw Nation was 'blazed out' by the Spanish Government. From this horse path were lateral paths blazed out by the settlers to their settlements. Corn, rice, indigo, and tobacco were the only agricultural products then introduced. Cotton gins were unknown, mills were unknown, and corn had to be converted into meal by means of coffee mills and the mortar and pestle. Nothing could be spared from the scanty subsistence of the settler for market. The bear, the catamount, the panther, and the wolf destroyed pigs and calves, poultry, and corn fields. Sheep were unknown. In a great measure the pioneer had to rely on his trusty rifle for the 'creature comforts' of life. Peltry, tobacco monopolized by the Government, indigo, and white oak staves transported in piroques to Natchez and N. Orleans were the only articles of commerce and the pioneer's only dependence for a supply of sugar, coffee, medicines, powder, and lead. I heard my father say that he never saw the day his family suffered for want of food or raiment; but for the first 15 years of his married life he did not see $15 in money that he could call his own. My mother and a negro woman...did the 'chores' of the household, spun the thread and wove the cloth for the entire family, white and black. My father, two negro men and two women, cleared the field, built the cabins, cultivated the crops, and replenished the smoke house with wild game and fish. My older brothers and sisters fed the pigs, herded the cattle, gathered the eggs, and wormed the tobacco patch..."

— "The Life of Benjamin Grubb Humphreys"^[105][d]

Despite Humphreys' belief that the Spanish government had "blazed out" the Natchez Trace, the entire continent had long had an "intricate network of Indian trails. Many of the first routes taken by the settlers, and subsequently made into roads, originally were Indian trails," including the road between Nashville and Knoxville, and the route through the Shenandoah Valley.^[57] On July 15, 1789, Jackson was in the Natchez District swearing allegiance to the king of Spain so that he could trade there without paying a tax intended for non-resident American traders.^[108][109] The following month Natchez District planter Thomas M. Green Jr. granted power of attorney to the young lawyer.^[108] Jackson could also pursue his hobbies in Natchez: there was a quarter-mile racetrack at Natchez-Under-the-Hill as early as 1788, and the St. Catherine course, later to come to fame as the Pharsalia Race Course, was likely in operation by 1790.^[110] The jockeys and grooms at these tracks were enslaved Blacks, and horses and slaves alike were used for stakes.^[111][112]

Jackson might have been a transient or itinerant trader, which was common.^[113] If he had a physical store it would likely have been log-built, or possibly the frame cabin of his "emigrant boat" deconstructed and rebuilt to the same purpose on land.^[8][114] According to biographer Robert V. Remini, young Jackson made the acquaintance of "a great many Natchez businessmen and through them began an extensive trading operation."^[115] Preserved letters from 1790 between Jackson and "Melling Woolley, a Natchez merchant" record goods being carried from Nashville to Natchez, including "cases of wine and rum; also a snuff box, dolls, muslin, salt, sugar, knives and iron pots."^[116] Another letter of 1790 thanks Jackson for his help with the "Little Venture of Swann Skins," which historian Harriet Chappell Owsley asserted were feathers or down stuffing for pillows and mattresses,^[117] but which some scholars suspect was a euphemism for a shipment of slaves.^[116][118] According to Remini, "On one occasion he returned a runaway slave to the Spanish governor of Natchez, Manuel Gayoso de Lemos, for James Robertson."^[115] An estimated 70,000 enslaved people were imported into the United States from overseas between 1791 and 1807,^[119] but fortunately for Jackson, business opportunities abounded for American slave-traders in 1790s Natchez, because the beginning of the Haitian Revolution in 1791 disrupted the once-reliable supply of slaves from the Caribbean until after the Spanish left Mississippi in 1798.^[120] This same revolt disintegrated the undergirding of a dual-hemisphere Napoleonic empire and opened the way for the Louisiana Purchase.^[121]

The study of Jackson's earliest slave trading is closely tied to the study of the Robards–Donelson–Jackson relationship controversy. Jackson and Rachel Robards née Donelson ran off together sometime between the summer of 1789 and July 1790,^[122] leaving behind Rachel's allegedly abusive first husband Lewis Robards.^[123] An 1890 news article purporting to tell "the true story of the great statesman's matrimonial venture" claimed that "near Natchez...there used to stand a ruined log hut, which was pointed out to strangers as the spot where they had passed their honeymoon. This was, no doubt, the spot to which he carried her when they first ran away..."^[124][e] For that matter, in the first decade of the 20th century, a man named E. R. Jones repeatedly asserted that his father, Rev. John Griffing Jones, a native of Jefferson County and "pioneer Methodist historian in Mississippi,"^[126] had been insisting since the 1870s that Rachel Jackson Robards had had a double log house with an open hall ("two pens and a passage") on a small farm located 1.5 miles (2.4 km) southwest of Old Greenville on the Natchez Trace, opposite his father's birthplace at what was called Belle Grove plantation. Rev. Jones said this farm, where Andrew and Rachel were married (in the Biblical sense, if not the legal), had a spring, later known to locals as Jackson Springs, and oldheads remembered that garden mint had naturalized around the spring and associated creek.^[127][128] In any case, the young couple returned to Nashville in a party of 100 or more via the Natchez Trace in July 1790, with Hugh McGary attesting at Rachel's divorce proceedings that the couple were "bedding together" on the journey.^[122] By 1792 Jackson had finances sufficient to buy Poplar Grove on Jones Bend in Davidson County.^[129] In 1794, the year Jackson and Rachel Donelson were legally married in Tennessee, the Spanish reported that the Choctaw and Chickasaw were looking to them for food, and were collectively "in a wretched condition...[some] dying of hunger."^[130]

In his letters, Jackson referred to the path from Natchez to Nashville as a journey through "the wilderness."^[131] Another traveler described the Trace in early days as "an impenetrable forest condensed by cane and cemented by grape vines, so that a dozen trees must be cut before one can fall..."^[132] British traveler Francis Baily described the rustic nature of the Natchez road in his journal of a 1796–97 trip, with the one-room "tavern" at Grindstone Ford being so unpleasant that he preferred to sleep outside under a tree.^[133] Baily also wrote about "encamping grounds," describing wide places in the road, especially at river fords, that were identified by the presence of felled trees, extinguished campfires, and compacted soil.^[134] In times of high water, travelers would swim across the intervening rivers and streams, accompanied by cargo rafts built on the spot, so that provisions and supplies could stay dry.^[135] According to an Ohioan, travelers returning northeast on the trace usually went on Opelousas horses, "a small breed of mixed Spanish and Indian...very hardy and accustomed to subsist on grass and the bark of trees. To every three or four persons there was one or more spare horses to carry the baggage."^[136] Still, despite its unimproved nature, the trail was already a well-trafficked trade route in the 1790s—a stretch of the southern section was called the Path to the Choctaw Nation, and the run from Tupelo to Nashville was called the Chickasaw Trace—and Choctaw, Spanish, and American leaders alike were preoccupied with protecting and extending their access to the road.^[137][138]

It is unclear where Jackson collected the enslaved people he carried south, and in what quantities of people he trafficked. Until Robertson's 1794 Nickajack Expedition tied off the bloody conflict with the Cherokee, the Cumberland district remained "as violent a world as any American ever inhabited."^[139] Nashville proper remained but a small settlement in this era, with a total population in 1800 of about 350 people, approximately 150 of whom were slaves.^[82] The states of Delaware, Maryland, and Virginia were "already net exporters" of slaves in the 1790s, shortly joined by the District of Columbia, and North Carolina, whereas Tennessee, admitted in 1796 as the 16th U.S. state, would not become a net exporter of slaves until the 1850s.^[140][141] Historians know not to what purpose Jackson "crossed the wilderness between Knoxville and Nashville twenty-two times—once alone, 'when the Indians were most numerous and hostile.'"^[142] Knoxville was the Tennessee starting point for the Philadelphia Wagon Road (Jackson's brief service in the House and the Senate certainly gave him occasion to visit the national capital), and from 1798 to 1804, he had the travel obligations of a state judge.^{[143][144][145]} During Nashville's earliest history, "Philadelphia being the favorite market of the Nashville merchants, they would leave here on horseback, and it would take them nearly six weeks to reach the city of 'Brotherly Love'. All purchases were then sent through by wagons."^[46] Similarly, at the turn of the 19th century, shipping between Baltimore and Nashville involved "six-horse teams at a cost of ten dollars per hundred pounds."^[146] The land route to either city was tiresome, requiring arduous travel through the Blue Ridge Mountains or up around the Alleghenies.^[147] In 1795, Jackson set off on a work trip to Philadelphia intending to buy trade goods and to sell lands that were still legally under Indian title.^[148] There Jackson "traded land preemptions for flour, sugar, piece goods, and pocket knives."^[80] Before Jackson departed, friend Overton cautioned him, "If you purchase Negroes in any of the northern States, be careful in so doing not to subject yourself to the penal Laws of the State."^[148][f] On November 30, 1799, Jackson agreed to a slave swap between himself, John Overton, and a man named Carter. Jackson was to take a couple owned by Carter, writing Overton, "They will [serve] my Purpose to Sell again."^[150]

Upstream from Natchez c. 1807 by William Constable [d]; view of Petit Gulf in the 1820s by Charles Alexandre Lesueur; Natchez landing in the 1830s by Henry Lewis; the mighty Mississippi, probably in the 1840s, painted by Robert Brammer [d]; New Orleans levee in 1841 by William James Bennett, Vue Generale de la Nouvelle-Orleans c. 1854 by Théodore Müller [d]

In his 2013 biography, Andrew Jackson, Southerner, historian Mark R. Cheathem wrote, "Historian Charles Sellers once argued that after 1804 'never again was Jackson to engage in any considerable speculative venture.' The facts do not bear out this claim. Jackson speculated widely in land during the 1810s in an effort to benefit himself. Given his direct involvement in land seizures during the 1810s and his subsequent correspondence about prospects in Alabama, Florida, and the Mississippi Territory, it stretches credulity to imagine that he did not calculate these moves to help his land-speculating associates turn a profit as well."^[151] Similarly, Jackson was still opportunistically trading slaves well into the 19th century, certainly until his actions during the War of 1812 made him a national figure. According to Frederic Bancroft's Slave-Trading in the Old South (1931), letters in the Jackson papers at the Library of Congress demonstrate his continuing interest in the market.^[152] For instance, territorial governor William C. C. Claiborne wrote to Jackson from "near Natchez" on December 9, 1801, with an update on local markets:^[153]

"The Races in this District, commenced yesterday, and will hold for three days; Mr. Hutchings has attended the Race today, and will proceed from thence, to Mr. Green's, where he has left the Negroes & Horses. Mr. H. will be at my House, next Week; in the mean time, I will try to find a purchaser for your Horses, as for Negroes, they are in great demand, and will sell well. There is hardly any Corn in this District, and so soon, as the pumpkins give out, Horses will Suffer, & hence it is, they are not at present in demand; But if Mr. H. should bring his horses to Natchez, I will try to sell them, to the best advantage."^[153]

A couple of weeks later, an update from Claiborne:^[154]

"I had the pleasure to deliver in person your Letters to Mr. Hutchins; he is now at my House, & is in good health & Spirits. The Negro Woman he has sold for 500 dolls. in Cash, and I believe he has, or will in a few days sell the Boy, for his own price, to Colo. West. The Horses are not yet disposed of, but I hope he will meet a purchaser, in a day or two. I shall on Tomorrow, set off for Fort Adams, & Mr. Hutchings has promised to accompany me; previous to our return, I hope, we shall be enabled to sell the Horses. I can assure you, with great truth, that Mr. Hutchings is a prudent, amiable young man, & is very attentive to your Interest."^[154]

The John Hutchings who appears in some reports and documents associated with the slave trade was Andrew Jackson's nephew-by-marriage.^[155] Rachel Donelson's older sister Catherine married Thomas Hutchings; John Hutchings was their firstborn son.^[156] According to the editors of The Papers of Andrew Jackson, Hutchings was "Jackson's partner in the Lebanon, Gallatin, and Hunter's Hill stores."^[157][g] The Jackson–Hutchings–Coffee triumvirate also had a store at Muscle Shoals, Alabama.^[159] On Christmas 1801 Hutchings wrote Jackson with his own update on the sale items described by Claiborne, declaring, "I shall meet with no dificulty to sell the negres...you may rest asurd that money is my hole thought and Im sir your most obt. Sevent."^[160] The tandem vending of horse flesh and human flesh was common. As Bancroft explained in 1931, in many antebellum Southern marketplaces, "the same man dealt in horses, mules and slaves."^[161] Similarly, Calvin Schermerhorn, writing about the ocean-going (rather than riverine), or "coastwise" slave trade, stated, "On nearly all American coastal voyages on which slaves were transported in the 1810s and early 1820s, the accent fell on shipping nonhuman cargoes," meaning that the "main" cargo was coal or rum or cowhides or cotton or porcelain, but shippers moving goods between any two points where slavery was legal were as likely as not to have a few slaves aboard as well, bound for resale wherever inventory was low and prices were high.^[162]

In 1803 Jackson took custody of an enslaved black man named Bird; Jackson had served as security for a $500 credit line extended to a free white man named Mark Mitchell; when Mitchell could not pay, Jackson repossessed Bird to resell to raise some or all of the money owed.^[163] In 1804, as Jackson's Tennessee stores busily traded steel for bear skins,^[164][165] he wrote a long letter arguing with a trading partner about their arrangement:^[166]

"...that he would sell if possible at new orleans, and that I wished you (as I had before stated to you in person) to receive your proportion of your debt at New Orleans, that Mr. H would carry on negroes to exchange for groceries, and wishing you to make a sale of them before he came if you could, that a fellow answering the description you wanted was bought, but I was fearfull he would not suit you as he had once left his master and so forth but as to stating that he had sufficient funds with him to pay all our debts cannot be correct..."^[166]

In 1926, historian John Spencer Bassett wrote in The Correspondence of Andrew Jackson, "This letter shows Jackson's method of carrying on a controversy in his early life. It also contains the clearest available evidence that his trading firm bought and sold negroes."^[167] Jackson was up to his neck in debt that year, so, Remini summarizes, "To pay what he owed, Jackson returned full time to his business interests in 1804. He resigned the judgeship, sold his plantation at Hunter's Hill (where for a time he had operated a small store and from a narrow window sold goods to the Indians), disposed of an additional 25,000 acres he held in various parts of the state (he continued his land speculation despite the Allison disaster)...Through consolidation and liquidation he managed to pay off all his debts. It meant starting all over again financially, and it meant living in a log cabin once again."^[168]

In June 1805, Jackson wrote Edward Ward, the buyer of Hunter's Hill, that he could not accept slaves as a form of payment, because of timing: "I cannot believe that you are seriously impressed with the belief, that you are now authorised to discharge a part thereof in negroes—had negroes been offerred before Mr Hutchings descended the river with negroes for sale they would have been recd."^[172][150] Some traders worked all year to collect what were called "shipping lots" of slaves, but Jackson apparently rejected Ward's midsummer offering as inauspiciously timed.^[173]

Also, according to Gen. Jackson's Negro Speculations, Jackson bought an enslaved man from a Dr. Rollings of Gallatin in 1805 or 1806, with the intent to resell him in the "lower country," and later sued the doctor over the child's health condition.^[174] This "Dr. Rollings" of Gallatin may be the Dr. Benjamin Rawlings of Sumner County, Tennessee who wrote Jackson in 1798 at the request of their mutual friend Overton, who "told me yesterday Evening that your Negro George had got Snake Bitten And Requested if I was acquainted with any Salutary medicine" for it; Rawlings recommended a plantain poultice, and "If the leg and foot is Much Sweld Bleeding wuld not be Amiss I am Sir With Respect &c. Ben Rawlings."^[175] The documents timeline in The Papers of Andrew Jackson includes three mentions of a case known as Andrew Jackson and John Hutchings v. Benjamin Rawlings. The suit seems to have been initiated in approximately September 1805, a decision was rendered in September 1808, and an appeal decision was handed down in March 1813.^[176][h] There is an 1828 letter from Jackson "casually" explaining that possession of this "negro boy," who had been "kept at the Clover Bottom at our store," had been uncertain in part because he was abducted as the result of "a race...the stakes...which was to be in cash or negroes as I understood."^[179][112] The "negro boy" in question was named Charles and had been born in approximately 1793, meaning he was about 12 years old when Jackson had purchased him for purposes of resale.^[180] In the Correspondence, Bassett annotated this Jackson letter with the note: "An article in the Nashville Banner and Whig of Aug. 1, 1828, had brought up this incident in support of the charge that Jackson was a negro trader. That he took slaves in settlement of accounts and sold them for money is undoubtedly true. But he was never a negro trader in the ordinary meaning of the term."^[181] ¯\_(ツ)_/¯

In October 1828, the final issue of the Monthly Anti-Jackson Expositor published a letter that had allegedly been written by Jackson to William P. Anderson in January 1807. (Anderson, a U.S. Attorney and father of future Confederate general J. Patton Anderson, had been one of Jackson's closest associates in the 1800s and 1810s, but by 1828 had turned into a lacerating critic.) Per the Expositor, "When...[Jackson's] correspondence, such as is actually and unquestionably his own, comes to be inspected...All the rules of composition, of orthography, and of syntax, are disregarded, and a most reprehensible ignorance is made manifest...The occasion of writing it...was the receipt of the President's proclamation respecting Burr, and a letter from the Secretary of War on the same subject. And it is certainly remarkable for the cool indifference with which private receipts, a negro-trading bargain, contempt for the Secretary of War, and consultations for the suppression of a supposed wide-spreading treason are commingled together."^[182] As to the bargain, Jackson had written Anderson, "...the Negro girl, if likely, at a fair price, I will receive...if you [find it] Convenient bring the girl with you..."^[182]

In March 1807, Jackson purchased 15 slaves at a sheriff's auction of the property of his neighbor and brother-in-law Robert Hays (appointed in 1797 to be the first U.S. marshal of the new-formed federal judicial district of Tennessee),^[183][184] and then conveyed those 15 slaves to Jane (Donelson) Hays.^[185] Hays had recently declared bankruptcy, and during the 1828 election this action was alleged to be a conspiracy intended to defraud Hays' creditors, essentially money laundering enslaved assets.^[186] Jackson's trading activity had seemingly ramped up again in 1807, as in February there was also an exchange with Samuel Dorsey Jackson involving a "growing gaming debt" and a "Negro woman."^{[184][187][188]} Samuel Jackson wrote Andrew Jackson, "I would like to keep her as long as it was in your power to do without her, as we have but little help."^[189] Bassett annotated one line in the first of two letters with the comment: "This sentence seems to mean that the negro woman was to go on the boat."^[189] A month later, on March 6, 1807, 40-year-old Andrew Jackson jumped 55-year-old Samuel Jackson on the street, such that "on May 15, 1807...a Davidson County grand jury presented to the Mero District Superior Court an indictment against Jackson for 'assault with intent to kill' Samuel Dorsey Jackson." The reported motive for the attack was an unpaid debt; Andrew Jackson was acquitted of the charge in November 1807.^[190][i]

Neither the range of topics covered in the letter to Anderson nor Jackson's metamorphosis from negro speculator to warlord to U.S. president were coincidental. In the words of political scientist Michael Paul Rogin, "Jackson...won and lost land in horse races, mixed slave trading with land deals, and was plagued like other speculators by problems of tax liens, imperfect title, Indian claims, and bankruptcy. Other speculators lived with these problems and sought to resolve them pragmatically. They had turned virgin land into money; they remained in the material realm in the conflicts that resulted. Jackson, however, did not. His personality and the threat to his fortune forced him to return to the nature of things. Worldly success failed to rescue Jackson...and establish his authority in the world...Plagued by title conflicts and insecure possession, he went back to the Indians, at the beginning of it all."^[196]

In 1810, Andrew Jackson, Joseph Coleman (the first mayor of Nashville), and a "probable" resident of Natchez named Horace Green formed a business partnership on the existing system of transporting trade goods, slaves, etc. downriver from Tennessee to the consumers of Louisiana and Mississippi.^{[197][198][j]} Slaves owned by this firm became part of the propaganda leafleting and news coverage of Jackson's business dealings during the bitter 1828 campaign.^[198]

According to a political opponent writing as "Philo-Tennesseean," some of the enslaved people that Jackson collected before the outbreak of the War of 1812 were gleaned from a US$4,000 (equivalent to $73,248 in 2023) horse-race bet lost by Newman Cannon,^[k] who paid up in cash, a horse, and 11 slaves, which collectively represented "the earnings of many years honest labor." Philo-Tennesseean also alleged that Jackson fixed races and asked, "Did you not always carry about with you, to horse-races, cock-fights, &c. a set of bullies, who were ready to fight for you on the slightest occasion? and did they not, on some occasions, when there was a dispute, take the 'stakes' by force?"^[201][l] (In regard to the charge that Jackson fixed races, a 1897 history by John Allison hinted at "indiscretions" and allowed that there were perhaps a "few spots on the otherwise white flower of a blameless life" when it came to Jackson's career in "sport.")^[203] It was common to treat slaves as a cash equivalent: as debt collateral, by mortgaging them, or by putting them in the pot of a poker game. Slaves were "liquid assets" that served as a ready currency for land owners with unreliable income. The financial system of the frontier U.S. south was based on the inherent fundamental value of the enslaved, all while guaranteeing a lifetime of insecurity for the people used as security.^{[204][205][206][207]}

On November 26, 1811, Jackson paid US$450 (equivalent to $8,240 in 2023) for a 14-year-old boy named David.^[208][209] The seller was 63-year-old Charles M. Hall who lived near the Clover Bottom.^[210][211] The bill of sale was witnessed by John Coffee.^[208][209] Other slaves that came into the joint ownership of Jackson, Coleman, and Green were bought from a Mecklenburg County, Virginia, tavern owner named Richard Epperson.^[197] Per historian Snow, "In essence, the men only paid a down payment of $2,500 on a total agreed price of $10,500 in cash. The rest of the principal was to be paid in two six-month installments. However, when Green...subsequently abandoned the slaves in Natchez, Jackson became entirely responsible for both the debt and the costs of transporting the slaves back to Davidson County."^[197]

The Port Gibson Correspondent newspaper published an "extra" edition on September 13, 1828, to address the subject of Jackson's work as a slave trader.^[212] The Port Gibson coverage was reprinted in Peter Force's National Journal, which was "the official organ of the John Quincy Adams administration."^[213]

"We have, with astonishment, observed the attempt in Nashville to brow-beat and bully the most respectable gentlemen from asserting publicly what is the absolute truth: that Gen. Andrew Jackson was, in the year 1811, a dealer in Negroes: and, believing it to be our duty to expose falsehoods and to aid the truth, we do now assure all men, whether the friends or the opponents of Gen. Jackson, far and near: That in the fall of the year 1811, Gen. Jackson and John Hutchings did descend the river Mississippi and land at Bruinsburg at the mouth of the Bayou Pierre in this county, with from twenty to thirty negroes: that a number of those negroes were brought to this immediate neighborhood, and afterwards encamped for weeks at Mr. Moore's in the McCaleb settlement, ten miles from this town; that on the 27th of December, 1811, Gen. Jackson sold three negroes, "a woman named Kissiah, with her two children, Reuben, about three years old, and a female child at the breast called Elsay, in and for consideration of the sum of $650."—that on the 28th of Dec. 1811, the very day after the former sale, and while at the same encampment, he sold to Mr. James McCaleb, of this county, two other negroes, named Candis and Lucinda, for the sum of $1000:—that he sold other negroes in this county during that trip;—that he sold some at or in the neighborhood of Bayou Sarah;—that after the belief became general in this country that war would be declared against Great Britain, the planters were indisposed to buy negroes, as the market for their cotton would be closed, Gen. Jackson resolved to return to Tennessee, with the remnant of his drove; that while he had his negroes encamped near Mr. James McCaleb's, and was making his preparations to pass through the Indian nation, he was informed by one of the most respectable citizens of this county, now living in it, of the law requiring passports for slaves; of the resolute character of Mr. Dinsmore, and of his punctilious execution of the duties of his office as Indian Agent: These things we do most unequivocally and unhesitatingly charge and assert. We do so on the best of authority,—the notoriety of the facts; the declarations gentlemen of whose truth no doubt can or will be entertained; from written documents, of various kinds, in the hand writing of Gen. Jackson himself: as also from the affidavit of Mr. William Miller of this county, who came down on board the boat with Gen. Jackson and his negroes; all of which we have heard and read. These things Gen. Jackson cannot, dare not, and will not, himself deny; whatever he may suffer others to do."^[212][m]

According to "Sidney" in the Natchez Ariel, the slaves Jackson sold in late 1811 were "landed in chains at the Petit Gulf, in Claiborne county; as far as I can learn about a dozen were sold in that county...Not finding purchases for more in Claiborne county, Gen. Jackson brought the remainder down to Washington [the territorial capital, located in Adams County] and then to Natchez, where he exhibited them for sale, and the General was notoriously considered at that day as nothing more than a negro trader. About two years after it is thought by many that he took his degrees which qualify him for the presidency—'there indeed was a rise.'"^[219] Abolitionist William Wells Brown wrote about visiting Natchez and Rodney (renamed from Petit Gulf in 1828) circa 1830, when he was the teenaged servant of a Missouri-based slave trader: "We landed at Rodney and the slaves were driven to the pen in the back part of the village. Several were sold at this place, during our stay of four or five days, when we proceeded on to Natchez. There we landed at night, and the gang was put in the warehouse until morning, when they were driven to the pen. As soon as the slaves are put in the pens, swarms of planters may be seen in and about them. They knew when Walker was expected, as he always had the time advertised beforehand when he would be in Rodney, Natchez, and New Orleans."^[220]

While returning to Nashville with his unsold stock, Jackson got into a dispute with an Indian agent named Silas Dinsmoor.^[n] Dismoor was determined to enforce a regulation requiring that every enslaved person crossing through the unceded Choctaw lands carry a document identifying their legal owner and the purpose of their travel. The intention was to prevent runaway slaves from using the Choctaw lands as a refuge, which in turn would hopefully reduce complaints from white settlers about the Choctaw. Jackson disliked Dinsmoor enforcing this rule, and while traveling, had to pass the Choctaw Agency in company of a "considerable number of slaves." Dinsmoor was not at the agency when Jackson passed by. Still, Jackson left a message promising a future confrontation with Dinsmoor, who persisted in regulating the passage of enslaved people over the Trace. Jackson later saw to it that Dismoor was removed from his post.^[222] Jackson, affronted that this issue was being resurfaced in 1828, wrote, "Did I not inform you that the Sub agent Smith (Dinsmore not being there) had collected about 400 armed Indians with about sixty white men, to stop or destroy me, if I attempted to pass the agency without exhibitting a passport...that the demand was an act of usurpation...I was determined to exercise this right, and resist & put down, at the risque of my life, this petty usurper..."^[223] According to Jackson's political opponents, "It is notorious that he did not take a passport, but when he approached the Agency he armed his negroes with axes, hired some half breed Indians with their arms—marched by the Agency in military order, himself at the head, with the cap of his holsters thrown back, and his rifle cocked."^[224]

Jackson's ire seemed to stand out, even on a frontier road regularly traveled by hardened boatmen, quarrelsome Kaintucks, horse-stealing Indians, gangs of homicidal highwaymen, and bounty hunters seeking the heads of fugitive slaves.^{[226][227][228][229][230]} Historian J. M. Opal found "no evidence of any general uproar against the Indian agent. Indeed, the very existence of so many passports suggests a rough consensus between most settlers and a Jeffersonian regime eager to oblige them. Once again, men like Jackson had interests and ambitions that made exceptional demands upon the various authorities around them."^[231] A retired American military officer, Alexander McIlhenny of Frederick County, Maryland, who had been stationed at Washington Cantonment in Mississippi Territory during the War of 1812, said as much in a letter to the newspaper in 1828: "...the general, having sent forward his negroes, had mounted his horse, and laying his hand upon his pistols, significantly replied, 'These are General Jackson's passports!!!' I have often thought of this anecdote of Mr. Dinsmore's whenever the Constitution, laws, or the orders of government, have thwarted the arbitrary will of this man. Shall weapons of war be his passport to our suffrage, and to the Chair of State?"^[232]

There are three 1812 letters from the then-44-year-old Jackson about this specific platoon of slaves for sale, which was initially under the purview of Green and which he later took control of himself. Jackson wrote in 1828 of this much-disputed coffle that "it was said, [Green] was squandering it, by card playing."^[223] Jackson wrote in 1812 that there were 27 people in the group: "...25 grown negroes; with two sucking children they always count with the mother,"^[233] and that 13 of the group were women, as they needed "habits."^[234] As is the case in nearly all surviving letters written by participants in the American slave trade, Jackson's letters are marked by "insensitivity, self-congratulation, and deeply racist complacency."^[235]

In the first letter, dated December 17, 1811, and addressed to his wife, Jackson wrote "on tomorrow I shall set out from here homewards, on the Biopierre I expect to be detained Some days preparing the negroes for the wilderness My trusty friend John Hutchings, on the recpt of my letter had come down to this place recd. all the negroes on hand and had carried them up to his farm—I have Just seen Mr. [Horace] Green last evening this morning he was to have Seen me, but as yet, he has not appeared as to the State of the business I can give you no account—untill I have a Settlement with him or have an account of the appropriation of the amount of sales from him I shall bring home with me from twelve to Twenty—I hope to be able to sell some of them on the way at good prices—but many of them I Shall be obliged to bring home and as most of that number will be females I leave you to point out to Mr John Fields [Hermitage overseer] where to have the house built for them."^[237] Ten days later, he found a buyer for the mother and children, Kessiah, Ruben, and Elsey.^[238] The day after that he sold Candis and Lucinda.^[238]

On February 8, 1812, Jackson wrote to his sister-in-law Mary Donelson Caffrey: "The negro fellows that I brought thro with me owing to their exposure in the wilderness have all been sick and were the well neither of them is such that I could recommend to you—nor could I think of selling such to you..."^[239] He also advised her that the "convulsed state of the Earth and water from the frequent shocks" of the 1811–1812 New Madrid earthquakes had disrupted river traffic to such an extent that she would be better off buying someone already down south.^[239]

Then, in correspondence of February 29, 1812, he made time for a multi-page complaint about the business acumen of young Horace Green.^[240] Jackson wrote that "...the highest Expence of any that did accrue during the time we were engaged in the mercantile transactions was (including provissions hands and return expence)" was $250, whereas Green had spent $318.75. Jackson continued, "I also found from examining the acpts of Negroes sent to markett that the expence never averaged more from here than fifteen dollars a head," with the solitary exception of "one wench and three children, who had been subject to the fits remained better than six months in the Natchez" having cost him $25. Jackson argued to the arbitrators to whom he was writing that Green's business expenses were "exorbitant" and that Green did not even provide an itemized report, but rather lumped "charges without any specification." Jackson continued that "taking no notice of the time the negroes have been hired out, or the reduction of their expence by sales, and one having run away" there was a balance of $340 but "from every enquiry I have made on the subject, that fifteen dollars pr head is about the usual expence, and finding this to amount including the amount of the Price of the Boat, and not taking into view the children at the breast, it makes the cost on each negro $44.66,2⁄3" which per Jackson was "more than double what is usual..."^[241]

Jackson proceeded to lay out a list of expected expenses for such a slaving expedition, based on "the soldiers ration," including the anticipated cost of crewing the boat (with a steersman), housing for Mr. Green "after he left his Boat," two purchases of cornmeal (totaling 100 bushels) for $62.75, two purchases of bacon for $208.121⁄2, as well as an expected clothing expense for at least the female slaves: "one habit each the fellows recd naked."^[234] The standard diet for slaves on the march was pork and cornmeal, but, per Sydnor, "as there was no economy in providing new clothes for the journey through the forests, negroes generally reached the market in rags."^[242]

They had hired a keelboat, and Green "had on board a number of Negroes" who could be put to work pulling the oars. An oar-propelled keelboat was better for going upstream than a flatboat (which essentially treated the Mississippi as one long flume ride).^[244] Jackson argued that if Green had sense he never would have made a sales call at Natchez, which everyone knew was "glutted" with slaves and slave traders, but instead he should have visited the prosperous old settlement of Bayou Sara (further downriver near Baton Rouge) and then gone up into the Red River country of Louisiana and sought buyers there. This type of circuit was the life of a slave trader, most of whom "seem to have stayed only a short while in any one place."^[113] Green instead landed at Natchez where he traded some of the slaves in his possession for what Jackson called "an old horse foundered."^[245] If Green had been a better steward of this merchandise, wrote Jackson, the slaves in question "would have cleared their own expence, if not neated something to the owners."^[245]

And measured out our length, as once our height. How far
From home our luggage takes us!
But, farther, still, Our hanker; till a trail's eroded
Down how far we've come. Rock in belly, bullet in gut,
Axe in skull, quelling passion in whatever name,
Kill pain; but ache out-aches the crime,
The gun. Somewhere along the trace, our spill
Of blood will tell the others who and what we were.

— Marvin Solomon, "The Natchez Trace" (August 1962)^[246]

• Mean age of people sold: 14.67 years old
• Mean price of people sold in 1811 only: US$330 (equivalent to $6,043 in 2023)

(Note: Small sample size likely makes this data meaningless.)

Several of Jackson's bills of sale are dated to late December, at the end of the Mississippi cotton season—"A few days' rest usually coincided with Christmas."^[252] Winter and spring were the traditional slave-trading seasons, after the harvest was in, and before the summer heat and mosquitoes and fleas arrived in force.^{[147][253][254][o]} The river was also higher in winter and spring, and the current stronger, making for a faster trip downstream in the days before steam power.^[256]

The receipts for several slave sales made by Jackson resurfaced in part because buyer Abraham Green had died October 6, 1826,^[257] and his estate was still being settled in 1828.^[258] One of the executors of Abraham Green's estate, Benjamin Hughes, had the bill of sale for Kessiah and her children notarized before sharing the documents with the Ariel.^[250] As it happens, Hughes was probably kin to Eden Brashears, an assistant agent at the Choctaw Agency.^[259] The Port Gibson Correspondent stated that the sale record for Malinda and Candis to James McCaleb was entirely in Jackson's handwriting (except for the signatures of the witnesses) and "could be viewed at the office of the Democratic Press at any time between the hours 8 a.m. and 5 p.m. daily."^[251] According to May Wilson McBee's extracts of Natchez District court records, in 1804 James McCaleb had filed a claim for "555 acres on Boggy Br. of North Fork of Bayou Pierre, 3 mi. east of Grindstone Ford, Plat shows 513 acres adj. Wm. Kilcrease, John Robinson, Abner Green and the old survey of Catura Proctor."^[260] According to a newspaper ad placed by P. A. Van Dorn (who married another daughter of Mary Donelson Caffrey, and who was the father of future Confederate general Earl Van Dorn), McCaleb also operated a cotton gin near Bayou Pierre in 1814.^[261] The McCaleb family history states, "James McCaleb was considered a bad manager by his brothers. He never became quite as wealthy as they, but he was very well off in his day."^[262]

The Washington Jackson & Co. that accepted the $1,000 for Candis and Lucinda from James McCaleb on behalf of Andrew Jackson was a cotton factor, or cotton brokerage firm, with branches in New Orleans, Philadelphia, and Liverpool, England.^[263] Cotton factors were "the most important middlemen" between Southern crops and Northern and European markets.^[264] Factors often held crops on consignment and acted as not just business managers for plantation owners but as banks, taking a stake in the consignee's business and perhaps advancing them money against future profits.^[265] According to historian Harold D. Woodman [d], "By 'endorsing' a planter's note, the factor guaranteed that it would be paid when due. The planter would receive credit, but the factor would not be called upon to make any cash outlay unless the planter defaulted."^[266] There were three Jackson brothers, John, James, and Washington, who were "Irish immigrants but with no verifiable relationship to Andrew."^[267] In 1809, Washington Jackson had a store in Natchez, where he had an extensive inventory, including a "first rate new keel boat, 25 tons burden, with poles and oars" advertised for sale in September,^[268] and where he sold a slave woman prone to "fits" to a "free French" woman of color on behalf of Andrew Jackson in December.^[269] According to The Papers of Andrew Jackson (1984), James Jackson served as a "private banker for Andrew, extending large sums of money on promissory notes. They were later partners in numerous land ventures, including the Chickasaw Purchase speculation."^[267] Another instance of Jackson treating the Jacksons as slave brokers appears in a letter of September 18, 1816, written to Rachel: "Mr James Jackson on your application will take order on Sampson if necessary, that family will sell any where, better below than in Nashville, but I suppose in Nashville for $14. or 1500." The Sampson in question was apparently "Big Sampson with wife Pleasant and son George," who had been purchased as a family in Mobile in 1814, shortly after the city was captured from the Spanish in April 1813.^[270][89]

Top left: Natchez District, Mississippi Territory c. 1800, showing "Fort McHenry," Fort Adams, the very first subdivisions, Adams and Pickering counties, and the towns of Ellicotville (later Selsertown), and Huntston (later Old Greenville); top right: Natchez District c. 1816, showing mileage between stands on the Natchez Trace, "Gibsonsport" (later Port Gibson) and the Grindstone Ford; bottom left: Natchez District c. 1823 in the last days of the Trace as a U.S. government post road; bottom right: the Natchez District c. 1856, showing railroad lines, and Louisiana towns on the opposite site of the Mississippi River

The first account of "Jackson as slave trader" that was published after his death comes from an author writing as Idler, datelined Rodney, Mississippi, 1854: "...here [at Bruinsburg], nearly fifty years ago, Gen. Jackson—he was not 'Old Hickory' then—landed his flatboat, laden with Western produce, negroes, etc., which he had piloted from Nashville. I have understood that the original intention of Jackson was to settle in Mississippi, but he subsequently returned through the wilderness to Tennessee..." Idler continued, explaining that "the removal of negroes through the Indian nation into one of the States of the Union was strictly prohibited," and there was a plan made by the Choctaw and their allies "to arrest him by force should he persist in his unlawful attempt" but Jackson "armed his negroes and a few of his friends and boldly marched unmolested through the Indian territory."^[271][p][q]

"Idler" described Jackson participating in foot races and wrestling matches at Bruinsburg, naming "Bruin, Price, Crane, Freeland, Harmon and others" as Jackson's companions in sport.^[271] Jackson's most astute 19th-century biographer reported that as a youth, "He was passionately fond of those sports which are mimic battles; above all, wrestling...He was exceedingly fond of running foot-races, of leaping the bar, and jumping; and in such sports he was excelled by no one of his years."^[275] Among those taking an oath of allegiance to the United States, on October 30, 1798, were Waterman Crane, Lewellin Price, and James and Hezekiah Harmon.^[276] These men swore their oath before Samuel Gibson, a resident since 1788 and the founder of Port Gibson, the principal village of upper Bayou Pierre.^[277]

A surviving letter written to Jackson on October 21, 1791, by George Cochran, mentions "many agreeable hours" spent at Jackson's "friendly retreat at Bayou Pierre."^[115][278] In 1801, Cochran bought land on Bayou Pierre from Crane, property that was adjacent to land owned by territorial judge and Bruinsburg namesake Peter Bryan Bruin, and George Humphreys, father of future Confederate general Humphreys.^[279] One of the Humphreys' properties was called the Hermitage,^[105] a name that supposedly inspired the name of the Tennessee plantation Andrew Jackson established in 1804.^[280] When the Confederate general's grandfather died, back in the day, he owed money to "many creditors, including Jackson."^[281] In 1802 Cochran was involved in the operation of Bruin's saw mill, "now cutting cypress planks," located on James' Run stream near Bruinsburg and Bayou Pierre.^[282] The same year, Bruin advertised that he was laying out an 11-street town at Bruinsburg and was seeking investors: "SUBSCRIPTIONS will be received at Natchez, by Robert and George Cochran, Ebenezer Rees, Bryan Bruin and at the Office of the Herald; at Cole's Creek by Thomas Calvit and John Giraults; at Bayou Pierre, by James Harmon, George W. Humphreys, Arthur Carney and William Scott; at Big Black, Tobias Brashears; at Fort Adams, by Capt. James Sterret."^[283]

The memoirs of William Henry Sparks, published in 1870, described his knowledge of Jackson's slave-trading business: "Many will remember the charge brought against him pending his candidacy for the Presidency, of having been, in early life, a negro-trader, or dealer in slaves. This charge was strictly true, though abundantly disproved by the oaths of some, and even by the certificate of his principal partner."^[284] Sparks said that Jackson had a "small store, or trading establishment...which stood immediately upon the bank of the Mississippi" at Bruinsburg, and there was an accompanying race track and a cockfighting pit, and people told stories for years after about Jackson's "skill" at these sports. Per Sparks, Jackson sold slaves in the vicinity of Claiborne County, including to Sparks' father-in-law Abner Green and his wife's uncle Thomas M. Green Jr. Sparks claimed to have "bills of sale for negroes sold to Abner Green, in the handwriting of Jackson, bearing his signature..."^[284]

"Sometimes, when the price was better, or the sales were quicker, he carried them to Louisiana. This, however, he soon declined; because, under the [redhibition] laws of Louisiana, he was obliged to guarantee the health and character of the slaves he sold. On one occasion he sold an unsound negro to a planter in the parish of West Feliciana, and, upon his guarantee, was sued and held to bail to answer. In this case he was compelled to refund the purchase-money, with damages. He went back upon his partner, and compelled him to share the loss. This caused a breach between them, which was never healed. This is the only instance which ever came to my knowledge of strife with a partner. He was close to his interest, and spared no means to protect it."

A 1912 biography comments, "The biographers of Andrew Jackson strain and strive mightily to ignore the fact that their hero was a negro trader in his early days, but it is a fact nevertheless...Ordinarily, the Memories of Fifty Years is to be rejected as an authority: the book was written in the extreme old age of the author and is full of fable. But William H. Sparks himself married into the Green family,^[r] lived in the Bruinsburgh neighborhood, and must be presumed to have known what the Greens had to say concerning their great friend and his beloved wife."^[286]

Sparks also recalled that when he and his wife visited the White House in 1835, 67-year-old widower Jackson asked them, "'Is old papa Jack and Bellile living?'...These were two old Africans, faithful servants of her father; and then there was an anecdote of each of them—their remarks or their conduct upon some hunting or fishing excursion, in which he had participated 40 years before."^[287]

George Catlin painted Indigenous Americans many times, including View of the Lower Mississippi  [d] c. 1860s (showcasing the region's native people and storied loess soils), Breaking Down the Wild Horse  [d] c. 1834, and Ball-play of the Choctaw – Ball Up  [d], which depicts what McCaleb calls the Indian ball game—Catlin saw the game played in Indian Territory in 1834, after Indian removal, where he also painted a portrait of Tul-lock-chísh-ko (He who drinks the juice of the stone), who was considered the best ball player in the Choctaw nation

Dr. James F. McCaleb, writing about the Natchez Trace in the Natchez News-Democrat in 1915,^[s] described Jackson as a sportsman and gambler, stated that he had stores at both Bruinsburg and Old Greenville, and that: "Grindstone Ford lane, one mile in length, on the Natchez Trace was the great rendezvous for horse racing, the Indian ball game, and lacrosse. Travelers from Kentucky and Tennessee stopped at the station of Mrs. Worldridge and the tavern of George Lemon near the Grindstone Ford on Bayou Pierre to enjoy the regular Sunday festivals.^[t] ...Among the horsemen from the Blue Grass State was A. S. Colthrap, who ran his horse against General Jackson's betting four slaves to determine the winner as well as some money. Colthrap lost his horse, his money, and his slaves to General Jackson, returning home a poorer and a wiser man."^[292][293] Per historian and Jackson biographer Bassett, "Race paths were laid out in the earliest [Southern] settlements and succeeded by circular tracks, as the settlements developed."^[294] In a study of antebellum horse racing, the Journal of Mississippi History recounted the Jackson–Colthrap incident and stated that this straightaway was the first racecourse in Claiborne County and was located near the "Red House" tavern at Rocky Springs.^[295] Also, according to the memoir of a Presbyterian minister, Sunday was indeed race day in the vicinity of Old Greenville, an attraction that drew many young men away from church attendance.^[296] Neither report addressed whether Jackson kept his winnings for personal use or resold them for short-term gain. There is an E. S. Coltharp (1784–1859) buried at the old Rocky Springs Methodist Church cemetery on the historic road from Natchez to Nashville.^[297] This Dr. James H. McCaleb who wrote an article about the Natchez Trace for the Natchez News-Democrat in 1915 was a great-grandnephew of the James McCaleb (1772–1822) who purchased Malinda and Candis from Andrew Jackson in 1811.^[292][298]

According to the county historian for Warren County, Ohio, a local plow manufacturer called John E. Dey travelled widely in the early 19th century via the Mississippi and Ohio River, seeking customers for the company's products. Dey spent his winters at Bruinsburg, and "Andrew Jackson, years before when he was just a Colonel, lived at this place. Colonel Jackson quite often frequented the plantation, and Mr. Dey became well acquainted with him. He remembered that he was a tall, slim man, with a nervous manner. He used to carry a pocket full of shelled corn and play with the grains at the dining table...He says that Colonel Jackson, soon after he came to Mississippi, went back into the woods about four miles from the river to a noted hunting place of the hunting gentlemen of the country. Here he started a saloon which he continued for many years. He never appeared behind the bar, but the establishment was his and he was responsible for it."^[299]

In 1922, Jackson biographer and former mayor of Knoxville, Tennessee, S. G. Heiskell described Jackson's Mississippi business as "slaves and whiskey."^[125] Letters and tax records show Jackson sold whiskey from a still running at his Hunter's Hill plantation in Tennessee in the 1790s.^[300] Whiskey was the beverage of early Mississippi, while gambling could have been considered the "unofficial state sport."^[301] Corn was the primary staple grain of both Tennessee and Mississippi. The earliest-dated document (albeit not in his hand) in the papers of Andrew Jackson, created March 29, 1779, is a training diet for a fighting cock. The directions were to give him finely chopped "Pickle Beaf" three times a day, "lighte wheat Bread Soked in sweet Milk," smoke-dried Indian corn, and "feed him as Much as he Can Eat for Eaight Days."^[302]

Last but not least, according to the slave narrative of James Robinson, published in 1858, when Andrew Jackson needed more men in the lead-up to what became the Battle of New Orleans, he visited the plantation of Calvin Smith on Second Creek near Natchez in approximately December 1814.^[303] Smith gave Jackson permission to take a large number of his slaves, and suggested more slaves could be gotten from Springfield, the plantation of Thomas Green.^[303] According to Robinson, Smith was willing to part with his slaves because he could always buy new ones whereas if the British captured and sacked the Mississippi River Delta his own irreplaceable children might be killed.^[303] Judge Bruin had worked with Smith's brother Philander Smith on territorial administrative and judicial issues.^[304][305] Thomas Hinds, one of the American military heroes of the War of 1812 in the southwestern theater, was also married to a daughter of Springfield.^[306] Jackson had kinship ties to the Green family that connected him to Springfield and the Natchez Junto, the Green–Hinds–Hutchins–West political alliance in Mississippi Territory.^[307] (Abraham Green's mother-in-law and Andrew Jackson's wife were sisters.)^[308] Robinson concluded his narrative with a warning to other American slaves: "Do not forget the promise Jackson made us in the New Orleans war—'If the battle is fought and victory gained on Israel's side, you shall all be free,' when at the same time he had made a bargain with our masters to return home again all that were not killed. Never will a better promise be made to our race on a similar occasion...Avoid being duped by the white man—he wants nothing to do with our race further than to subserve his own interest, in any thing under the sun."^[309]

It was well for him that he took the precaution to have our guns unloaded when in the ammunition house. His guilty conscience smote him, and told him he was doing us a great piece of injustice, in promising us, by the most solemn protestation, that we should be free if the victory were gained. I would then have shot him dead a thousand times, if that could have been done.

— James Robinson, 1858^[310]

If I had known that Jackson would drive us from our homes, I would have killed him that day at the Horseshoe.

— Tsunu′lahuñ′skĭ (anglicized Junaluska), Cherokee leader, quoted in 19th Annual Report of the Bureau of American Ethnology, 1900^[311]

American abolitionist Benjamin Lundy covered reports of Jackson's slave trading in his newspaper, The Genius of Universal Emancipation, or American Anti-Slavery Journal and Register of News. In 1827, when the first allegation appeared in Kentucky, Lundy recounted a separate story about Jackson having whipped a recaptured runaway slave he had tied to the joist of a blacksmith shop. Lundy could not confirm the secondhand report, and expressed hope that the reports of slave trading were exaggerating this tale.^[314] As the election approached in 1828, Lundy wrote that he felt that Jackson's own account of the deal was effectively a full confession: "This, we repeat, is Gen. Jackson's own story. It amounts to this. A speculation was to be made in cotton, tobacco and negroes: Coleman was to do the business and Jackson to furnish the means; the negroes were bought up, taken to market, followed by Jackson, part of them sold by himself at Natchez, and the rest carried back by him to Tennessee in the year 1812."^[315]

The close examination in 1828 of Jackson's enslavement of people like Gilbert, and his history of slave trading, was promulgated in large part by a man named Andrew Erwin, who, according to historian Cheathem, was "determined to undermine Jackson's campaign" for both spite and politics.^[316] Erwin and Henry Clay shared a set of grandchildren.^{[317][318][319]} Boyd McNairy, whose bank had held accounts for Coleman, Green & Jackson, and who published a broadside headlined "Jackson a negro trader," was a brother of John McNairy, the federal judge who gave Jackson his first law job in Nashville, and Nathaniel A. McNairy, who dueled John Coffee in 1806 and advertised slaves for sale in Natchez in 1807–08.^{[320][321][322]} B. McNairy later wrote in a public letter to Jackson, "You have been charged...with having been engaged, in one or more instances, in NEGRO TRADING—with having employed your capital and credit in the purchase and sale of slaves, for the sake of pecuniary profit. Is this charge true, or is it not? If it be true, why do you not magnanimously and heroically admit it, and defend yourself upon the ground that the habits prevalent in the country and the peculiar state of our society, in a community where slavery unfortunately exists, justified such speculations?"^[323]

Even though "the slaves he bought and sold as a young man as part of the burgeoning interstate trade in enslaved people helped make him rich," during the 1828 United States presidential election, Jackson repudiated the claim that he was a slave trader.^[324] Jackson's dishonesty was not his alone. Allies were recruited to swear, falsely, that it was not true. The editorial page of The Ariel of Natchez wrote that it was "a matter of astonishment that the friends of Gen. Jackson have the hardihood to deny that in the year 1811, their idol was not actually and personally engaged in the sale of Negroes as an object of speculation, because like almost every other charge brought against him, the more they endeavor to 'hide the crimes they see' and to screen him from odium, the deeper they impress on the minds of the investigating the strength of the evidence which support them."^[250] As retold by Mississippi historian Eron Rowland in 1910, "It may cause some of the warm friends of Old Hickory to scoff to recall the accredited fact that he, in those early days, for a time followed the business of a negro-trader at this place [Old Greenville, Mississippi]. A proof that this fact was not taken with the best grace at that day is that in several political campaigns, his followers were compelled to swear by the eternal that he did not."^[325]

Abolitionists Theodore Dwight Weld, Angelina Grimké, and Sarah Moore Grimké, under the banner of the American Anti-Slavery Society, wrote in American Slavery As It Is (1839) that "It is well known that President Jackson was a soul driver..."^[328] Lewis Tappan wrote in the margins of his copy, now held in the Amistad Research Center at Tulane University in New Orleans, that Weld said the statement about Jackson was the only thing anyone had ever denied or claimed was incorrect in the book, and further noted, "Mr. Weld informs me (Nov 23|49) that the above was stated to him by J. G. Birney who received it from Mr. Kingsbury, missionary among the Choctaws."^[329][u]

The denial was carried forward—for years, decades, daresay, centuries—by those whom Southern chronicler Harnett T. Kane described as "fist-pounding partisans."^[338] In his Jackson bio published 1861 (the first year of the American Civil War), Parton wrote:^[339]

"There is an odium attached to this business in the slave States, as is well known; and consequently, the alleged negro trading of General Jackson has excited a great deal of angry controversy. I was myself informed, in a mysterious whisper, by a southern gentleman in high office, that this was the only 'blot' on the character of the General. It is not necessary to investigate a subject of this nature."^[339]

Regarding the repeated appearance of the word odium in contemporary accounts of Jackson's trading, historian Sydnor wrote in his 1933 Slavery in Mississippi, "To the present day a certain odium clings to the term slave-trader. It may seem illogical that owners of slaves, who from time to time purchased from traders, would have scorned men in this business, but this seems to have been the case. It is debatable whether the disapproval of the trader in negroes was honest, or whether it was a convenient sentiment which made the slave-trader a scapegoat for much of the evil of slavery."^[340] Parton, apparently unbothered by the "blot" or the odium, wrote, "The simple truth respecting it, I presume, is, that having correspondents in Natchez, and being in the habit of sending down boat-loads of produce, the firm of which he was a member occasionally took charge of negroes destined for the lower country, and, it may be, sold them on commission, or otherwise."^[339] Nearly 120 years later, in volume one of his three-volume Jackson biography, Remini recapitulated Parton's conclusion almost in its entirety, further downplaying to posterity the importance of slavery in Jackson's life and work:^[341] "...because he had agents in Natchez and regularly sent down boatloads of produce, Jackson occasionally engaged in slave trading as a service for a friend or a client."^[342] Historian Cheathem argued in 2011 that due to an over-reliance on Parton, Remini, and the Correspondence, at the expense of archival investigation, Jacksonian scholarship has long minimized his slaving, and while "recent research by historians" has resurfaced the political significance of Jackson's slaveholding "...more work remains to be done on his own slave communities in Tennessee and Mississippi and the ramifications for his public actions."^[343]

Several of Jackson's personal and political conflicts involved the trade. According to American Slavery As It Is, Andrew Erwin's son James Erwin and son-in-law Henry Hitchcock were slave traders: "It is known in Alabama, that Mr. Erwin, son-in-law of the Hon. Henry Clay, and brother of J. P. Erwin, formerly postmaster, and late mayor of the city of Nashville, laid the foundation of a princely fortune in the slave-trade, carried on from the Northern Slave States to the Planting South."^[328][345] Similarly, in an early letter about the 1806 duel in which he killed Charles Dickinson, Jackson wrote, "...for the present it will only be observed that the deceased, could not be called a Citizen of this state—that he was engaged in the humane persuit of purchasing Negroes in Maryland and carrying them to Natchez & Louisa and thus making a fortune of speculating on human flesh..."^[346] In 1882, the Denton Journal described a derelict outbuilding on what had once been Dickinson's property near Preston, Maryland, where "staples and ringbolts" for chaining slaves were still embedded in the "massive timbers" of the old barn, originally constructed as a trader's slave pen.^[347]

Jackson pointed the finger again in 1819. According to Binder, "Jackson tangled with William Crawford, a severe critic of his Florida adventure. Jackson had information which linked Crawford with the alleged slave-smuggling activities of Georgia's former governor, David B. Mitchell. On September 28, 1819, Jackson, the former slave trader, wrote a 'Private' letter to President Monroe proposing an investigation of Crawford's activities..."^[351][v] This, argued Binder, writing in 1968, was a part of a lifelong pattern in Jackson's dealings with slaves and slavery, in which he remained "emotionally uninvolved" while alternately using appeals for and against various moral and social positions in pursuit of his own ends: "He viewed slavery as a convenient weapon of political warfare for obtaining objectives often quite remote from the Negro...His attitude toward the Negro appears to have been governed at all times by immediate and practical expediency. Whether in the fields of commerce, plantation management, military tactics or politics...He thought of the Negro in the present tense and appreciated him primarily as a tool in hand."^[352][w] Jackson repeatedly used hypocritical means in service of selfish ends: He criticized his political nemesis Clay as "'the typical western gambler,' obviously forgetting that he too fit the description."^[354]

Further along in the timeline, Jackson's First Seminole War begat the Second Seminole War during his presidency, which was triggered in part because "a unified band of defiant Native Americans and African Americans was a dangerous symbol when located so closely to a burgeoning plantation society built on the backs of enslaved people."^[355] Former slaves found some degree of safety and prosperity in the sovereign Seminole lands.^[356] The fact that Seminole leaders simply refused to allow these people to be turned back into products was intolerable to the Jackson administration.^[355][357]

Perhaps most importantly, Andrew Jackson's early arrival in the Deep South as a businessman led to his role in the Battle of New Orleans, extinguishing British hopes of regaining control of the lower Mississippi, and to his military conquest of the lands of the Old Southwest that remained in the hands of Indigenous people and the Spanish crown. Jackson's actions in the Creek War and the War of 1812 "greatly accelerated the transformation of ethnic relations already underway in the Mississippi Territory,"^[358] such that "the final shot in the Battle of New Orleans signaled the beginning of a race into the Old Southwest...with the acquisition of West Florida from the Pearl River to the Perdido, numerous waterways had become available for unrestricted shipment of cotton, timber, and naval stores to the seacoast."^[359] Turning and turning, in the widening gyre... In 1834, with Indian Removal well underway, The Liberator abolitionist newspaper published Nashville minister Marius R. Robinson's report on the internal slave trade: "In Mississippi and Louisiana the slave market is literally crowded. There are three principal reasons for the large demand.—1st. The high price of cotton last fall, induced many planters to go more largely into the cultivation of it, which increased the demand for laborers. 2d. The cholera has swept off thousands of negroes during the last two years, and the planters are now filling up the ranks made thin by this scourge. 3d. The country wrested from the Choctaw Indians has recently been brought into market. Of course the lands must now be cultivated by slaves."^[360]

Franchimastabé answered me that he had reason to believe that what I had told him was true, so he was determined to live prepared, as he was not unaware of the desire of the Americans to take the Lands of the Indians and always to impoverish them, which they were able to do.

— Journal of Stephen Minor, Spanish emissary to the Choctaw, March 27, 1792^[361]

What historian Andrew Burstein called "the political fashioning" of Andrew Jackson began in earnest shortly after the end of War of 1812 and continues to this day.^[32] Jackson's legacy remains a contentious topic.^[362][363]

Andrew Jackson's business model and actions met the definition of "slave trader" as understood by 19th-century abolitionists and 21st-century scholars.^[118] Still, as an 1828 campaign issue, "Andrew Jackson as human trafficker" got little traction. According to historian Robert Gudmestad, information about "Gen. Jackson's negro trading" failed to swing voters in part because "Southerners wanted to believe that there was a small group of itinerant traders who created most of the difficulties. It was this type of speculator, most thought, who destroyed slave families, escorted coffles, sold diseased slaves, and concealed the flaws of bondservants. They were the 'slave-dealers.' All others who bought or sold slaves, even if they did so on a full-time basis, were innocent."^[364] This privileged denial of the reality of the American interregional slave trade continued well into the 20th century. Joseph Erwin's biographer, writing in 1944, concluded in delusion: "Here as head of the firm, Erwin, Spraggins and Wright—Real Estate and Slave Dealers, Erwin speculated in plantations and 'trafficked' in slaves. However, he was not a designing speculator, bent on gain at all hazards, but the honorable, high-minded, upright dealer who believed that in business success could be obtained by self-reliance and honest and legitimate methods."^[365] In 1915, writing at the halfway point between Parton and Remini, a plantation heir named James T. Flint recycled the slave-trading-as-a-favor-to-neighbors shibboleth: "Andrew Jackson, who owned a few slaves in Tennessee, brought them down, with others belonging to friends, over the old Natchez trace to sell to well-to-do neighbors of his wife's former home near Greenville and Natchez, Miss., and for this reason he was accused by his political enemies in after years of being a 'nigger trader'."^[366] A few lines later Flint recorded that while visiting in the vicinity of Old Greenville, his forebears "talked with one of the negroes brought from Tennessee and one from Kentucky" sold in Mississippi by Andrew Jackson.^[366][x]

Further to the point, some Jacksonian scholars have argued that it was Jackson's status as a wealthy slave owner and slave trader that made him politically attractive to the electorate.^[367][y] If nothing else, according to biographer Remini, Jackson, his allies, and his successors believed "slaveholding was as American as capitalism, nationalism, or democracy...the white southern celebration of liberty always included the freedom to preserve black slavery. That states Jackson's own position precisely."^[370] In an 1841 column about local politics, the Mississippi Free Trader of Natchez defended the slave trade as the profession of a number of esteemed Southern gentlemen, listing as icons of genteel American prosperity John Armfield, Rice Ballard, Isaac Franklin, John L. Harris, Eli Odom, Thomas Rowan, and Sowell Woolfolk—"A desperate set of ruffians these, with old Andrew Jackson at their head!"^[371]

(1) American empire at the Gulf of Mexico, 1839; (2) Slaves enumerated in the diennal census, 1790–1840, represented as a percentage of the total population; (3) according to the legendary—in the medieval sense—of the Lost Cause of the Confederacy, Gone With the Wind (1939), "There was a land of Cavaliers and Cotton Fields called the Old South...Here in this pretty world Gallantry took its last bow...Here was the last ever to be seen of Knights and their Ladies Fair, of Master and Slave...Look for it only in books, for it is no more than a dream remembered"; (4) life in the Natchez District in the 1830s, as illustrated in American Anti-Slavery Almanac, featuring horse racing at the track, cockfighting (extensive), pistol duels, dull-normal stabbings, intermittent mass lynchings, high-stakes card games, the occasional eye gouging, manslaughter and murder aplenty, and torture of slaves in the United States

Historian Walter Johnson has described the lower Mississippi River valley of the antebellum United States as an anthropophagus landscape that fed on bodies and souls and turned them into American dollars: "The Cotton Kingdom was built out of sun, water, and soil; animal energy, human labor, and mother wit; grain, flesh, and cotton; pain, hunger, and fatigue; blood, milk, semen, and shit."^[372] Underlining the fact that the ethnic cleansing of Indigenous American people resident in the Old Southwest was prefatory to the establishment of a new economy and ecology predicated on the forced labor of African-American slaves,^[373] "when the surveyors hired by the General Land Office began their work in Mississippi in 1831, they used the 'Old Choctaw Line' as the 'base meridian' of their efforts to transform the landscape from a landscape of imperial violence to a field of national development."^[374] So here, behold, the gaping maw of the Slave Power, as it looked after the presidency of Andrew Jackson, mapped 1839 and printed 1845 by John La Tourette of Mobile, Alabama and engravers S. Stiles, Sherman & Smith of New York: "An accurate Map or Delineation of the State of Mississippi with a large portion of Louisiana & Alabama, showing the communication by land and water between the Cities of New Orleans and Mobile carefully reduced from the original surveys of the United States, being laid off into Congressional townships and divided into mile squares or sections, on the plan adapted by the General Government for surveying public lands, so that persons may point to the tract on which they live."^[374] American hegemony on the Mississippi and along the Gulf Coast is largely a product of Jackson's marauding.^[375] His ceaseless assault on the Indigenous people of the southeastern U.S. and his pioneering work in the for-profit forcible relocation of enslaved African-Americans yielded "the beginnings of rapid American economic development. The cotton kingdom...financed the American economic expansion of the succeeding decades."^[376] Stupid,^[377][z] greedy,^[284][379] and mean,^{[380][381][382][383]} Jackson's destiny was to expand and empower the young United States, but only "by violating many of its formal founding principles. If he had not done so, the United States would have different borders and fewer historical burdens today."^[384]

Slavery helped Jackson define the paternal state in whose name he removed Indians...But the slave model of paternalism, appropriate enough to Indian removal, contained force and violence at its core.

— Michael Paul Rogin, Fathers and Children: Andrew Jackson and the Subjugation of the American Indian (1975)^[385]

The blustering self-confidence and disregard of the sensibilities of others that critics ascribed to Jackson were traits he shared with many Americans, as were the predilection for violence and the tendency toward exaggeration. Certainly the insistence upon having one's own way and the willingness to use force...entered into the subsequent assault on the frontier along its whole length. To a considerable extent, these personal and national traits were elements in the phenomenal growth of the United States during Jackson's lifetime.

— Oscar Handlin, editor's preface, The Vindication of Andrew Jackson (1976) ^[386]

As you read, you will see, again and again, the same pattern acted out: A person or a group of people rejects injustice by rebelling and seizing the reins of power. As soon as those reins are in the hands of the rebels, the rebels become the establishment, the victims become the tyrants, the freedom-fighters become the dictators...Revolution shatters the structures; but the men who build the next set of structures haven't conquered the evil that lives in their own hearts.

— Susan Wise Bauer, The Story of the World, Vol. 4 (2021)

These things had other names once, before English or French or Spanish or Latin were even languages. A study of Natchez Trace toponyms noted, "The wary pioneer who 'said his prayers with his shotgun cocked' might notice a thrush or a butterfly but would not name a place for it..." reserving his animal place names only for those things that he could kill to eat or those things that could kill and eat him.^[387]

...his heritage, the land which old Carothers McCaslin his grandfather had bought with white man's money from the wild men whose grandfathers without guns hunted it, and tamed and ordered or believed he had tamed and ordered it for the reason that the human beings he held in bondage and in the power of life and death had removed the forest from it and in their sweat scratched the surface of it to a depth of perhaps fourteen inches in order to grow something out of it which had not been there before and which could be translated back into the money he who believed he had bought it had had to pay to get it and hold it and a reasonable profit too: and for which reason old Carothers McCaslin, knowing better, could raise his children, his descendants and heirs, to believe the land was his to hold and bequeath since the strong and ruthless man has a cynical foreknowledge of his own vanity and pride and strength and a contempt for all his get...

it was the new country, his heritage too as it was the heritage of all, out of the earth, beyond the earth yet of the earth because his too was of the earth's long chronicle, his too because each must share with another in order to come into it and in the sharing they become one...

— William Faulkner, Go Down, Moses (1942)^[388]

On Wednesday evening, April 29, 1863, a little over 25 years after the end of Jackson's presidency, a recently emancipated slave entered an Army of the Tennessee encampment on the Louisiana side of the Mississippi River and met with Major-General Ulysses S. Grant. The free man informed Grant of an excellent boat landing at Bruinsburg—entirely undefended, and much closer than the one Grant had planned to use. The next day, at the site of Andrew Jackson's old slave-trading stand, the U.S. Army made what stood until 1942 as the largest amphibious landing in U.S. military history.^[391]

General Grant and his men went on from Bruinsburg to capture Vicksburg, breaking the spine of the Confederacy at the Mississippi River.^[391]

• Family separation in American slavery
• Andrew Jackson and slavery
• Legal affairs of Andrew Jackson
• Presidency of Andrew Jackson § Slavery controversies
• Historical rankings of presidents of the United States § Scholar surveys of diversity and racism
• Political eras of the United States
• List of presidents of the United States who owned slaves
• List of slave traders of the United States
• Bibliography of the slave trade in the United States
• Bibliography of Andrew Jackson
• Robert V. Remini § Andrew Jackson
• John Quincy Adams and abolitionism