Andrew Jackson was a twenty year old attorney when he and Judge John McNairy rode into Jonesborough in the spring of 1788. Andrew passed the bar exam in Washington County and started a law practice to supplement his meager salary as state prosecutor for North Carolina. Some residents considered themselves citizens of the State of Franklin, others North Carolina. As an Attorney, he did well during the quagmire of legality created by the State of Franklin situation.
Andrew Jackson and Judge McNairy shared a loft with Mr. and Mrs. Christopher Taylor and their thirteen children. Two men sleeping together; one the judge the other his prosecutor would be considered a political scandal by today’s standards.
Andrew had made a name for himself in Salisbury, North Carolina where he apprenticed under lawyer Spruce Macay. Unfortunately, the reputation he made would follow him the rest of his life, regardless of his accomplishments.
In a heated moment of courtroom rage, the unknown Andrew Jackson challenged Waightstill Avery, a well-liked attorney in Jonesborough to a duel. Realizing how popular Mr. Avery was, Andrew had the opportunity to shoot Avery at point blank range; instead he raised his dueling pistol in the air and fired. The crowd applauded him, the barristers shook hands and their feud was over.
A decade later as a guest of the Chester Inn, Andrew Jackson woke to the smell of smoke, alerted the guests, and climbed on the roof of the inn to extinguish the fire. He saved the inn and the town of Jonesborough, becoming the town’s hero. Today the Chester Inn still stands as a Tennessee landmark thanks to his heroic efforts.