Early career of Andrew Jackson

Clerking and lawyering in North Carolina and the Southwest Territory (1784–1798)

Biographer James Parton wrote in 1861 that while Jackson had acquired "the little legal knowledge necessary" to practice frontier law "he never became, in any proper sense of the word, a lawyer." Historian C. Edward Skeen, in a review of The Legal Papers of Andrew Jackson (1987), stated, "Historians have written little about Andrew Jackson's law practice and career as judge of the Superior Court of Tennessee...this period of his life is largely a void...The editors are to be applauded for their considerable effort in producing this volume, but it would appear that all they have shown is that the documentary evidence of Jackson's legal career is too skimpy to be recovered."

Training

Information about Jackson's legal education is "sketchy and uncertain." In December 1784 he went to Morgantown, North Carolina, and sought the tutelage of Waightstill Avery, "a Princeton graduate and former state attorney general who...declined to take him on as a student." He then studied with lawyer Charles Bruce in Martinville, which was named for its chief resident, Founding Father Alexander Martin. Local lore has it that he may have worked at the "mercantile establishment" of Thomas Henderson and Thomas Searcy during his time in Guilford County—or very possibly the three were simply acquaintances who raced horses and fought cocks together. Jackson read law in early 1786 at the Salisbury, North Carolina law office of Spruce Macay, a socially connected lawyer and later a North Carolina state judge and state legislator. In late 1786 Jackson moved to the Montgomery County, North Carolina, law office of John Stokes.

North Carolina lawyer

In August 1787, Rowan County, North Carolina issued a warrant for the arrest of Jackson and two friends on charges of trespass. Jackson posted a recognizance bond, and "no further records exist, suggesting that the case was settled out of court or dismissed."

Jackson was tested by two judges, Samuel Ashe and John F. Williams, and admitted to the bar of North Carolina in September 1787. He then "drifted" through western North Carolina, handling cases in Randolph and Rockingham counties, but "it seems apparent...that Jackson found it difficult to attract clients." Among the cases Jackson handled at the Johnstonville courthouse in Randolph County was a dispute over beehives. Another surviving record from Randolph County states, "On motion of Andrew Jackson, Esquire, attorney for Absalom Tatum, it is ordered that Adam Tate, Coroner of Rockingham County, be fined 50 pounds nisi for failing to return fiere facias against John May, Sheriff of said county, at the instance of Absalom Tatum and that fiere facias issue accordingly."

Mero District attorney

Jackson was 21 years old when he arrived in "Nashboro" in October 1788. He was invited to the Mero District by his friend and fellow Macay law clerk John McNairy, judge of the Davidson County Superior Court, and was granted the unpaid position of county prosecutor and "acted as attorney-general for the state" at the November 1788 and May 1789 terms of the Superior Court. He was eventually granted a salary of £40. Jackson prosecuted 85 crimes "on behalf of North Carolina or the territorial government," predominantly assault and battery, some petty larceny, perjury, and horse thievery, as well as two felony murders, and one rape. He also "instituted more than thirty scire facias proceedings on behalf of the territorial government, presumably to collect fines for statutory offenses against court."

Private practice

Jackson also developed a private practice, filing more than 400 suits for clients between 1788 and 1798, predominantly in the Davidson and Sumner county courts, and the Mero District Superior Court. Matters at issue included lame horses, chattel slaves, real estate, and 1,453 pounds of beaver pelts. In the telling of legal historian James Ely, "Jackson's service to his clients involved more than preparation of pleadings and arguments in court. He functioned partly as a collection official and land agent. One client, on the losing side of a lawsuit, requested Jackson to convey a portion of a tract 'to the use of Setling the Judgment...obtained against me.' He further instructed Jackson: 'Sell the Balance for any kind of Trade and we can Settle when I return in the Spring.' On at least two occasions Jackson signed as security on his client's prosecution bond." Other lawyers working the vicinity at the same time included Josiah Love, John Overton, Bennett Searcy, and Howell Tatum; between the five of them they handled almost all the litigation in middle Tennessee. Jackson's legal practice was at its zenith in 1794 and 1795, after which he became more concerned with commerce and politics. There are only scant records that might illuminate Jackson's legal arguments but all of the legal systems in the Cumberland showed a "degree of continuity with colonial and English legal roots." In both his public and profit work, debt recovery was one of his specialties and since "he was on the side of the creditors, merchants were pleased to make use of his services."

Reputation

With regard to his reputation as an attorney, biographer and first editor of his collected papers John Spencer Bassett wrote "He was, no doubt, but little versed in the law." There are multiple versions of how Jackson came to challenge Waightsill Avery to a duel in 1788, but one retold in a history of western North Carolina had it that "Jackson had ridiculed Avery's pet authority—Bacon's Abridgment," and Avery's reply was "sarcastic...intimating that Jackson had much to learn before he would be competent to criticize any law book whatever." In 1796, John Sevier referred to Jackson as a "poor, pitifull, petty fogging Lawyer" (but two years later saw fit to appoint him to the Tennessee state bench). When the Magnesses were tried in 1810 for the murder of Jackson's friend and occasional business partner Patton Anderson, Alfred Balch was the prosecutor, and Felix Grundy and Jenkin Whiteside were the defense attorneys; Jackson was not involved in the trial except as a witness—"he was licensed to practice law and had served as a judge, but he and Anderson's friends had no delusions about his legal abilities." Bettina Drew argued in her influential thesis Andrew Jackson: Indian Removal and the Culture of Slavery (2001) that "Jackson was a continual law-breaker whose conception of the law was deeply Southern in orientation...In the slave-holding worldview, the law was an instrument of the master—the master was not, ideally, an instrument of the law—and it is this idea that Andrew Jackson lived by."

Ely states that Jackson was well-regarded: "Jackson experienced considerable success as a lawyer and enjoyed a favorable reputation. One litigant wrote to a friend: 'I wish you to put my Papers into the hands of an Attorney Lawyer Jackson if you can or into Mr. Overton or some good attorney...'...At the time of his death in 1793 [Josiah] Love had the largest case load [in the Mero District]. Second to Love at the latter's death, Jackson represented more clients than any other attorney for the period 1788–1796. Another measure of his standing in the profession is that Love and Searcy asked Jackson to represent them in private litigation."

Shopkeeping (1795–1807)

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." About 20 account books survive from Jackson's stores. Goods from Philadelphia resold in the Cumberland were marked up triple. Cotton from the Cumberland resold for double in New Orleans. 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." 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. As explained by a news writer in 1882, to be a merchant in Nashville at the turn of the 19th century was "vastly different" than it would be even 50 years later because the nation was then just beginning to build the vast internal transportation and communications networks necessary for commerce, and "Merchants usually kept a miscellaneous stock of goods, which stock was annually replaced by a visit to Baltimore or Boston. For several years goods were hauled by wagon from Baltimore to Nashville." In addition to manufactured goods, stock animals, and cotton, frontier Tennessee merchants dealt in slaves. For instance, 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 Andrew Steele's $150 past-due account at their store.

There were several stores in Tennessee and, briefly, one at a "cantonment" in what is now Alabama. Jackson's brother-in-law Samuel Donelson helped him open one such store at Clover Bottom in 1795, collecting goods that Jackson had sent down the Ohio River from Pittsburgh to Limestone, Kentucky, then bringing them overland down to Davidson County. The account books for this store use pounds, shillings, and pence. Among their many customers was Robert "Black Bob" Renfro, the keeper of a tavern in Nashville, to whom Jackson sold fabric, wine, and flatwares. The account book for this store includes several notations suggesting that it was perhaps used by men who held accounts with Jackson as a payroll service for hired-out slaves: "paid Negro George for you 10 shillings...paid a Negro pr your Verbial O[rder]...paid Negro for you 6 pence...[paid] your Order Negro Tom 2 pence...[paid] your Order favour Negro Nan 1 shilling 6 pence..." Goods for sale included "coffee, tea, sugar, chocolate, raisins, wine, pepper, 'Tobaccho', 'segars', knives, tea kettles, paper, ink, gloves, hosiery, combs, needles, linen, calico, handkerchiefs, ladies' and gentlemen's hats, bridles, stirrups, history and spelling books, and one entitled Hamilton on Female Complaints, to list just a sample!" However, since Jackson had bought all this based on the value of David Allison's notes, and Allison was defaulting, Jackson now owed the wholesale merchants in Philadelphia, and by June 1796, "The store had to be sold so Jackson's creditors could be paid. Jackson & Co. was dissolved...the brothers-in-law took a considerable financial beating."

In February 1802 he partnered with nephew John Hutchings and neighbor Thomas Watson in a store at Lebanon, two cotton gins, and a distillery. Watson exited the business in July 1803. Jackson was an investor in a "stand" at a "cantonment" on the Tennessee River near what is now Tuscumbia. Jackson and Hutchings jointly invested in the Clover Bottom development in approximately 1804–1805.

Early participation in state and national politics (1796–1798)

Andrew Jackson was a delegate to the 1796 Tennessee constitutional convention from middle Tennessee, along with Thomas Hardeman, Joel Lewis, John McNairy, and James Robertson. Jackson was an at-large U.S. Representative from Tennessee from December 5, 1796, to September 1797 (resigned), and a U.S. Senator from Tennessee from September 26, 1797, until April 1798 (resigned) during the 4th and 5th U.S. Congresses, which met at Philadelphia.

Tennessee state judge (1798–1804)

From 1798 to 1804, Jackson was one of three judges of the Tennessee Superior Court of Law and Equity. This was the state superior and appeals court, the lower courts were called Tennessee Courts of Common Pleas and Quarter Sessions. This was a combined criminal and civil court that "met twice annually in three judicial districts, Washington and Hamilton Districts in the eastern part of the state, and Mero District in what is now middle Tennessee." Washington District court was held at Jonesborough, Hamilton District court was held at Knoxville, and Mero District court was held at Nashville. Nashville was about 200 miles (320 kilometers)—by way of dangerous frontier horse paths and wagon roads—from Jonesborough and Knoxville. He oversaw some cases involving enslaved Blacks but "slave crimes were handled separately in special justices and slaveholders courts," and there was no appeals process that would bring the cases to his bench.

Jackson was initially seated under a recess appointment made in August 1798 by Sevier, and then he served the September term in Hamilton District and the November term at Mero District. Jackson was officially elected by vote of the Tennessee state legislature in December 1798, defeating Bennett Searcy, 18 to 13. Other historically significant figures who had the same judge job before or after Jackson included McNairy, Overton, Willie Blount, and Archibald Roane.

The three judges met twice a year in each of the three judicial districts for 12 to 15 days at a time. Day one was administrative and bureaucratic business followed by county justices of the peace and sheriffs submitting "return of recognizances, scire facias, and other writs. Constables were summoned and a grand jury impanelled." The judge work included overseeing trials, hearing motions, and deciding on appeals. The cases were mostly commercial litigation. Jackson "often presided over three or four jury deliberations daily, and during one hectic day he sat on seven trials." Criminal complaints were a comparatively small fraction of the docket, with few serious felonies, the most common charges were for assault, stealing horses, and "riot". Penalties of the era were harsh, for instance, Jackson joined in "rendering the death penalty on at least ten occasions. For instance, in May of 1802, Jackson handed down three capital sentences for horse stealing at a single term."

Per James Ely, one of the editors of The Legal Papers of Andrew Jackson, "It is difficult to probe the intellectual dimension of Jackson's years on the bench...Decisions were delivered seriatim by the individual judges. Although Jackson was prepared to exercise an independent judgment and to disagree with his colleagues, his opinions were brief and lacked extensive citation to legal authorities." Jackson had several extended absences and missed several sessions of court in 1803 and 1804, in two instances because he was traveling to Philadelphia to buy goods for resale at his stores. He began to contemplate resigning from the bench as early as 1801. In the telling of Ely, "Jackson's restless nature was not suited for the inevitable constraints upon a judge." The money was also no good, about which Jackson complained. (When Jackson sold Betty and her 15-year-old daughter Hannah to Abraham Green in Pickering County, Mississippi Territory on December 27, 1800, the sale price of $550 for the pair was almost equivalent to Jackson's $600 annual salary as a Tennessee state judge.) Jackson resigned from the bench on July 24, 1804, apparently for a multitude of reasons, including that being a state judge conflicted, since February 1802, with his elected office of major general of Tennessee militia. Sevier, for his part, had apparently come to regret the appointment: In 1803, Sevier journaled about a dream in which his dying father visited from heaven to share that everyone there was fascinated by the Jackson–Sevier abortive duel incident but also that "Jackson was by all viewed as a very wicked base man and a very improper person for a Judge."

Farming

In Tennessee, Jackson farmed at Poplar Grove, and then Hunter's Hill, and finally at the Hermitage beginning in 1804. He used overseers beginning in 1795, and his wife Rachel is frequently credited with holding together the slave-labor farm at the Hermitage during her lifetime, during the many periods when Jackson traveled for business, politics, recreation, and conquest. 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." One historian wrote of his agricultural investments: "He did not make as brilliant a success in farming as some of his neighbors. He lived in too high a manner for that." The "high manner" problems included imprudent financial investments, status symbol purchases, and extravagant wagers on sporting events. Still, Jackson "valued land and the independence that it provided; the success of his 'farms,' or plantations, consumed much of his free time throughout his public career."

Gambling

Gambling wins and losses seem to have been a consistent element of Andrew Jackson's income and outgo. One of the preserved anecdotes of his early life tells that, in 1784, while living in Charleston, South Carolina, he "saved his horse from having a new owner" by winning at rattle and snap, which was a dice game similar to craps. The neighbors recalled that while he was resident in Salisbury, N.C., he "played cards, fought cocks, ran horses, threw the 'long bullet'...carried off gates, moved outhouses to remote fields, and occasionally engaged in a downright drunken debauch." In Nashville, it was said of Jackson: "He had fine horses an he run 'em, he had fine cocks an he fit 'em." He also "probably gambled some with cards...[and] was devoted to the game of billiards." Jackson had a horse track and cock pit in Mississippi Territory. Jackson and friends organized a "cocking ring" to celebrate Independence Day at McNairy's Spring in Nashville in 1809. He was co-owner of a racetrack at Stone's River. There was gambling going on in this establishment, as well as throughout the settlement. (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.")

According to one study of sports and sports betting in the early American republic, "Andrew Jackson had made friends through cockfighting and racing...maintained an active racing stable through his presidency, and used his image as an active sportsman to appeal to voters."

Distillery and saloons

Letters and tax records show Jackson sold whiskey from stills running at his property beginning in 1798, capacity 197 U.S. gal (750 L), later reduced to 139 U.S. gal (530 L). He wrote to customers, "The whiskey you can have at any time in such quantities as you may think proper," and customers like G. M. Deaderick wrote Jackson with specific requests: "Should you not have made the whole of the Whiskey you intend for me, would be very thankfull to have one Barrel of at least one third Rye." Jackson's winter 1803 distillery record concludes, "Whiskey made, 370 gallons Sent to Store." In 1922, S. G. Heiskell described Jackson's Mississippi business as "slaves and whiskey."

Jackson had saloons. 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, Mississippi, 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." 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. Rawlings was married to a niece of Rachel Jackson. 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."

Boats and freighting

The Clover Bottom was also where Jackson's company sold and launched flatboats for other travelers going downriver. These boats had no propulsion, were barely steered, were most useful in winter and spring when rains kept the rivers high, and went only downstream, never up. In the words of Donald Davidson, a flatboat was a "broad-bottomed, boxlike structure, perhaps with a little rake at the bow. It was steered by a board fastened to a long pole, and was steadied in the current by clumsy, oarlike sweeps on each side, called 'broadhorns'. It was built of green timber sawed from the forest near the stream and put together with wooden pins...The roof might be gabled or round; one early observer described it as being 'like the roof of a carriage'. It covered at least half, or as much as two-thirds, of the boat. The larger flatboats measured up to 20 ft (6.1 m) by 100 ft (30 m) and could carry heavy loads—300 to 400 bales of cotton. The crudest possible type would be a mere log raft, with a shelter of rough boards, but the better boats might be fancied up considerably, with a pump to take care of leakage, and a brick or stone fireplace with a chimney, for cooking and good cheer."

Jackson's brother-in-law John Caffery moved his family to the lower Mississippi River valley in 1800 to serve as an "agent" for Jackson's business, offering in newspaper ads to "freight produce to New Orleans and act on his customers' behalf in selling their goods in New Orleans in exchange for 'five per cent on the [sale]'." In October 1800, Caffrey advertised that he would soon "descend the river to New Orleans" in boats that were being constructed at Lancaster's saw-mill at the confluence of Caney Fork and the Cumberland River near present-day Carthage, Tennessee. In 1936 a descendant wrote, "Their home was in Natchez, Miss., where John Caffery was engaged in the mercantile business, in the employ of Andrew Jackson."

There is a surviving 1803 contract between a riverman and Jackson's partner John Coffee arranging for a flatboat to depart from Haysborough, Tennessee for New Orleans loaded with 25 cotton bales and 77 hogs, which offers some sense of the scale of Jackson's shipments. In 1803 his firm built 27 boats "for the war department in expectation of difficulty with Spain in Louisiana." One of these boats, 12 ft (3.7 m) across the beam and 45 ft (14 m) long, and apparently never used for its commissioned purpose, was sold to Williamson County merchant John Hardeman on February 23, 1804, for US$45 (equivalent to $967.5 in 2025). 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. These boats were themselves valuable in the lower Mississippi, which had a shortage of planed lumber; they could be deconstructed and recycled into buildings and raised sidewalks.

Land speculation

According to biographer Robert V. Remini, Jackson's engagement with real estate investment started early in his life and continued "almost to the moment of his death," although historians have no clear insight into how profitable it was for him or even the full extent of his involvement. It was the combination of slave ownership and land speculation that "marked his entry into the planter class," elevating him above his roots as a fatherless runabout of the Carolina backcountry. Owning 20 slaves was the "traditional dividing line" between someone being considered a farmer and someone being considered a planter.

Some of Jackson's later Indian treaties may have opened lands to which his friends from North Carolina held "grants," such as lands north of the Chickasaw Bluffs (in what became Dyer County) which were claimed by Jackson familiars including his law teacher John Stokes, Ezekiel Polk, Hardy Murfree, Reading Blount, John Gray Blount, Wm. T. Lewis, William Hawkins, and Archibald Murphey.

Slave trading

In the telling of 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." Jackson carried slaves from the eastern states by land and water to middle Tennessee and then down the rivers by flatboat to the confluence of Bayou Pierre and the Mississippi River and there sold them to the planters of what are now Claiborne, Jefferson, and Adams counties, Mississippi. He sometimes ventured further south to sell to planters near Baton Rouge and Bayou Sara in the Feliciana section of Louisiana, and to brokers at New Orleans, but he reportedly preferred to sell in Mississippi because Louisiana's redhibition laws (which were essentially state-mandated slave warranties) complicated his trading.

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 politicians, militia officers, and "land-grabbers" were men whose "classifications...greatly overlapped." As a merchant, Jackson bought and sold as the market demanded, and as explained by researcher Bill Carey, "In the early 1800s, Tennessee's retail world had not advanced to the point where there were separate grocery, drug, and furniture stores. Customers bought all types of products from auctioneers, who might have furniture one week, blankets the next, and slaves the third." 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." It was common to treat slaves as a cash equivalent: as debt collateral, by mortgaging them, or by staking them on the turn of a faro game. (One of Jackson's friends from North Carolina was even accused of buying his way into a judicial clerkship with "the present docket profits and three negroes.") 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. An 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." In 1819, Overton asked Jackson to have John Brahan, of Huntsville, Alabama Territory, 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." According to Goodstein's analysis of 452 Nashville-area transactions involving approximately 700 enslaved persons 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."