The Jacksons returned to Nashville, where Andrew bought a small plantation, Poplar Grove, and left it to Rachel to run. Rachel was a cunning businesswoman, and the plantation succeeded splendidly under her watch. As Jackson's law practice continued to expand, so did his property–until he eventually settled on 650 acres of land that he named "The Hermitage." Indeed, Jackson often speculated in land throughout the early expansion of the West, buying or trading for tracts of wilderness when they were worthless and then waiting for the frontier to advance to his property.

In 1795, Jackson ran into his first major financial crisis, traveling to Philadelphia to sell nearly 50,000 acres of land he co-owned. After nearly a month, he found a buyer who paid twenty cents an acre in the form of promissory notes. Jackson, in turn, used the notes to buy goods to open a trading post on the Cumberland River in Tennessee. However, his partners in both ventures went bankrupt, and a bank notified Jackson that, as the promissory notes were no longer good, he would have to pay back the general store in Philadelphia where he purchased his goods. Jackson sold the store, only to find the man to whom he had sold the store was also bankrupt, which again left Jackson saddled with the cost again. He had to sell his second plantation and move into a shack on the Hermitage to pay back his bills. These bad experiences Jackson had with lending and borrowing led him to distrust banks and credit for the remainder of his life–a major factor in the Bank Bill crisis of his Presidency.

In the mid-1790s, the territory of Tennessee commissioned a census to determine whether the area met the 60,000-inhabitant threshold to be admitted as a U.S. State. When the census discovered that more than 77,000 lived in the area, the government ordered a convention to draft a new constitution and hopefully admit Tennessee to the Union. Andrew Jackson was selected as one of the five delegates from Davidson County. He and his fellow delegates traveled to Nashville on January 11, 1796, to begin the work. The convention debated and wrote the new constitution for twenty-seven days, during which Jackson made few major contributions. Popular lore says that Jackson suggested the name "Tennessee" for the new state, but many historians doubt whether he actually did. Jackson did second the motion to make the legislature bicameral, and he vehemently opposed a clause that would require all public officeholders to believe in God.

When Tennessee was admitted to the Union on June one, 1796, the offices were split between the two big parties in the new state: that led by John Sevier and the one with which Jackson aligned himself, the party led by William Blount. Sevier was chosen as the first Governor, and Blount and William Cocke were chosen as U.S. Senators. Jackson became the lone representative in the U.S. House. He arrived back in Philadelphia, then the nation's capital, just in time to hear George Washington's farewell address. However, three days into his first session, Jackson voted against a resolution honoring Washington because he felt that Jay's Treaty betrayed the new Republic to Britain–a vote that would later haunt Jackson as a Presidential candidate. Jackson served Tennessee well, and he was promoted to the Senate after that body expelled Blount amid scandal. Jackson did not stay a Senator long, as his financial problems were deepening back home. He resigned from the Senate to take a higher-paying job closer to home–an appointment on the state Supreme Court, where he served proudly for six years.

Never one to shy away from controversy, Jackson became entangled in a mess with Governor Sevier, angling to become major general of the state militia. Jackson lost the election twice before running successfully in 1802, narrowly beating Sevier. Sevier and Jackson almost came to blows in the street in Knoxville, and Sevier slandered Jackson's wife, charging her with adultery for marrying Jackson before her husband had completed a divorce. Jackson challenged Sevier to a duel, which turned into a comic farce where even the duel's seconds pulled pistols on each other. Indeed, even as Jackson advanced through life, he never lost his proclivity for dueling. Four years later, he killed another man in a duel over a horseracing bet.

After Jackson left the judge's bench, he returned to storekeeping. He and his two partners would receive goods in payment for their wares, and the storekeepers would then float the goods down the Mississippi to Natchez, to be sold at New Orleans. During this time, Jackson occasionally engaged in slave- trading, although he usually only allowed other owners to put slaves on his boats–slave-trading was too stigmatized for a gentleman to participate in. At varying points, however, Jackson did own up to 150 slaves to help run his various land holdings. By many accounts, though, Jackson treated his slaves relatively well compared to many slave owners at the time.

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