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In addition to his legal and political career, Jackson prospered as planter, slave owner, and merchant. He built a home and the first general store in Gallatin, Tennessee, in 1803. The next year, he acquired the Hermitage, a 640-acre (259 ha) plantation in Davidson County, near Nashville. He later added 360 acres (146 ha) to the plantation, which eventually totaled 1,050 acres (425 ha). The primary crop was cotton, grown by slavesJackson began with nine, owned as many as 44 by 1820, and later up to 150, making him among the planter elite. Jackson also co-owned with his son Andrew Jackson, Jr., the Halcyon plantation in Coahoma County, Mississippi, which housed 51 slaves at the time of his death. Throughout his lifetime Jackson may have owned as many as 300 slaves.
Men, women, and child slaves were owned by Jackson on three sections of the Hermitage plantation. Slaves lived in extended family units of between five and ten persons and were quartered in 20-foot-square cabins made either of brick or logs. The size and quality of the Hermitage slave quarters exceeded the standards of his times. To help slaves acquire food, Jackson supplied them with guns, knives, and fishing equipment. At times he paid his slaves with monies and coins to trade in local markets. The Hermitage plantation was a profit-making enterprise. Jackson permitted slaves to be whipped to increase productivity or if he believed his slaves' offenses were severe enough. At various times he posted advertisements for fugitive slaves who had escaped from his plantation. For the standards of his times, Jackson was considered a humane slave owner who furnished his slaves food and housing, and he did not prohibit his female slaves from having children.
The controversy surrounding his marriage to Rachel remained a sore point for Jackson, who deeply resented attacks on his wife's honor. By May 1806, Charles Dickinson, who, like Jackson, raced horses, had published an attack on Jackson in the local newspaper, and it resulted in a written challenge from Jackson to a duel. Since Dickinson was considered an expert shot, Jackson determined it would be best to let Dickinson turn and fire first, hoping that his aim might be spoiled in his quickness; Jackson would wait and take careful aim at Dickinson. Dickinson did fire first, hitting Jackson in the chest. The bullet that struck Jackson was so close to his heart that it could not be removed. Under the rules of dueling, Dickinson had to remain still as Jackson took aim and shot and killed him. Jackson's behavior in the duel outraged men in Tennessee, who called it a brutal, cold-blooded killing and saddled Jackson with a reputation as a violent, vengeful man. He became a social outcast.
After the Sevier affair and the duel, Jackson was looking for a way to salvage his reputation. He chose to align himself with former Vice President Aaron Burr, who after leaving office in 1805 went on a tour of the western United States. During that time he stayed for several days at the Hermitage. Burr's true intentions are not known with certainty. He seems to have been planning a military operation to conquer Spanish Florida and drive the Spanish from Texas. To many westerners like Jackson, the promise seemed enticing. Western American settlers had long held bitter feelings towards the Spanish due to territorial disputes and the persistent failure of the Spanish to keep Indians living on their lands from raiding American settlements. On October 4, 1806, Jackson addressed the Tennessee militia, declaring that the men should be "at a moment's warning ready to march." On the same day, he wrote to James Winchester, proclaiming that the United States "can conquer not only the Floridas, but all Spanish North America." He continued:
I have a hope (Should their be a call) that at least, two thousand Volunteers can be lead into the field at a short noticeThat number commanded by firm officers and men of enterpriseI think could look into Santafee and Maxicogive freedom and commerce to those provinces and establish peace, and a permanent barier against the inroads and attacks of forreign powers on our interiorwhich will be the case so long as Spain holds that large country on our borders.
Jackson agreed to provide boats and other provisions for the expedition. However, on November 10, he learned from a military captain that Burr's plans apparently included seizure of New Orleans, then part of the Louisiana Territory of the United States, and incorporating it, along with lands won from the Spanish, into a new empire. He was further outraged when he learned from the same man of the involvement of Brigadier General James Wilkinson, whom he deeply disliked, in the plan. Jackson acted cautiously at first, but wrote letters to public officials, including President Thomas Jefferson, vaguely warning them about the scheme. In December, Jefferson, a political opponent of Burr, issued a proclamation declaring that a treasonous plot was underway in the West and calling for the arrest of the perpetrators. Jackson, safe from arrest because of his extensive paper trail, organized the militia. Burr was soon captured, and the men were sent home. Jackson traveled to Richmond, Virginia, to testify on Burr's behalf in trial. The defense team decided against placing him on the witness stand, fearing his remarks were too provocative. Burr was acquitted of treason, despite Jefferson's efforts to have him convicted. Jackson endorsed James Monroe for President in 1808 against James Madison. The latter was part of the Jeffersonian wing of the Democratic-Republican Party.