Hogg joined the Transylvania Company in 1775, led by a former judge, Richard Henderson. In 1771, the same year Hogg defended the shipwreck from looters, Henderson was a presiding judge over the trial and execution of six Regulators. The Regulator Movement was an early form of backwoods rebellion, objecting over unfair colonial taxation and corruption. Once released from the bench in 1773, Henderson was free to pursue his burning ambition of land speculation.

The Transylvania Company’s goal, through the acquisition and settlement of the wild lands to the west, was no less than to create the 14th colony. In January and February 1775, James Henderson and some colleagues met with around 1,200 Cherokee who gathered in Tennessee for a Great Council.

In the Treaty of Sycamore Shoals, as it came to be known, the aboriginals were given six wagon loads of liquor, guns, ammunition, blankets and trinkets in exchange for some 20 million acres, making up most of modern-day Kentucky and eastern Tennessee.

Tsi’yu-gunsini (“He Is Dragging His Canoe”), a young chief from the Wolf Clan, objected to this European expansion.

“Whole Indian Nations have melted away like snowballs in the sun before the white man's advance,” he said on the second day of negotiating. “Such treaties may be all right for men who are too old to hunt or fight. As for me, I have my young warriors about me. We will hold our land.”

Things reached a breaking point when the colonists asked for even more territory — a Path Deed — as a conduit for settlement.

"We have given you this, why do you ask for more?” Dragging Canoe demanded. “When you have this you have all. There is no more game left between the Watauga and the Cumberland. You have bought a fair land, but there is a cloud hanging over it; you will find its settlement dark and bloody." Dragging Canoe and his warriors then left the meeting in protest.



According to Indian history, the man who would blaze the Path Deed trail, Daniel Boone, helped seal the Sycamore deal by plying the remaining older chiefs with whiskey. Oconostota and Raven Warrior were made so drunk that their interpreter had to guide their hands in order to sign the treaty.

According to White history, the liquor was rum, not whiskey, and the colonists virtuously kept it from Indian reach until the agreement was executed. English explorer John Lawson had already noted the effects of alcohol on the Indian population in December, 1700:

“Rum,” he wrote, “a Liquor now so much in Use with them, that they will part with the dearest Thing they have, to purchase it.”

The proposed 14th colony, founded on the land newly gained, was to be called Transylvania. James Hogg was dispatched to Philadelphia to negotiate official recognition from the Continental Congress. The petition was never considered: The treaty was seen as illegal by the English Crown as well as the colonies of Virginia and North Carolina, both of which ultimately voided the claim. According to European law, the Cherokee could not own land, and were thus incapable of selling any.



In the meantime, Daniel Boone blazed the Wilderness Trail through the Cumberland Gap, creating a highway for settlement to the west.