From this correspondence, it is clear that James was deeply involved in the various land speculation schemes of the Blount brothers. He made at least two trips to Philadelphia from Knoxville in 1794, an arduous journey of over 550 miles one way. On his trips to and from Philadelphia, James traveled the Great Valley Road which originated in Philadelphia and went west to Lancaster, Pennsylvania, before turning south to the Shenandoah Valley of Virginia. He would have stopped at inns and taverns along the road at Winchester, Harrisonburg, Staunton, Fincastle and Big Lick (Roanoke). The road split near Roanoke, with one branch going through a gap in the Blue Ridge to Salisbury and Charlotte in North Carolina. The other trail continued down the valley in a southwesterly direction to Fort Chiswell, Wolf Hills (Abingdon) and Sapling Grove (Bristol), and Colonel James King’s Iron Works, said to be a frequent stopping point for travelers. The trail split again at Sapling Grove, with one branch going to Jonesborough, Greeneville, Morristown, Mossy Creek (Jefferson City) and to Knoxville. The western road passed through Long Island of the Holston (Kingsport), Rogersville, Rutledge, and then on to Knoxville. When delivering messages and plats to William Blount’s brothers in North Carolina, James would have traveled the same routes used by Daniel Boone and the trail from Jonesborough, Tennessee, through Trade (Mountain City, Tennessee), West Jefferson, North Carolina, and Salem (now Winston-Salem) to Tarborough, North Carolina. Andrew Jackson and John Overton During the year 1794, James also formed a business relationship with Andrew Jackson and Jackson’s friend in Nashville, John Overton. Jackson was the brother-in-law of Stockley Donelson. It was undoubtedly through this relationship that Grant met Jackson. Andrew Jackson (1767-1845) was a lawyer and Superior Court Judge. He served in the U.S. House of Representatives and the Senate. In 1801, he became the Colonel of Tennessee State Militia, and during the War of 1812, he was the victorious commander of U.S. troops in the Battle of New Orleans. And of course, he was the seventh President of the United States (1829-1837). John Overton (1766-1833) was a prominent attorney, businessman, banker, land speculator, and advisor to Andrew Jackson. He succeeded Jackson as a Superior Court judge and became a Justice of the Tennessee Supreme Court. He was one of the founders of Memphis, Tennessee. Overton was also the son-in-law of General James White of Knoxville and the brother-in-law of Hugh Lawson White. James entered into a number of business arrangements with Jackson and Overton during the years 1794-95. In late December 1794, James received a letter from John Overton in Nashville regarding a correction to a previous instruction relating to a tract of land they were attempting to sell. Overton’s message, shown below, was hand-delivered to James by their mutual friend, Robert Hays.47 Colonel Robert Hays (1758-1819) was born in Salisbury, Rowan County, North Carolina, and died in Davidson County, Tennessee. He was a Revolutionary War officer (1778-1784) and spent over a year as a British prisoner of war. After the war, Hays moved to Tennessee and married Jane Donelson, the sister of Andrew Jackson’s wife, Rachel. He served as Colonel of Cavalry for the Mero District of Tennessee and was a prominent figure in the Nashville Lodge. He was also a surveyor, and over time, accumulated over 36,000 acres of land in Tennessee. Colonel Hays served as a Justice of the Peace, and in that capacity, he married Andrew Jackson and Rachel Donelson in 1794. In the same year, he was authorized to raise a fund to cut and clear a wagon road from Southwest Point (Kingston) to Nashville. In 1797, he was appointed Marshal of West Tennessee by George Washington. He served as Deputy Inspector and Muster Master during the war of 1812. In 1818, he was “…old and very infirm and in reduced circumstances.” He received a pension from the government, but “died poor” the following year. 47 Letter: John Overton to James Grant, December 10, 1794, Tennessee State Library & Archives, Nashville 57 .