The American Indians who frequented Kentucky, including from the Shawnee and Cherokee tribes, faced the prospect of the first permanent incursion into an area they had inhabited for some ten thousand years. The eighteenth century had brought with it greater but still limited exposure to outsiders, through European trade and religious missions. Boone and his fellow explorers represented a sea change, an attempt to set a course toward seizing Kentucky. The exact meaning of the name Kentucky has been lost, but it's believed to mean the "Land of Tomorrow" in one Iroquoian dialect, unintentionally matching these colonists' objectives, a grave threat to the local tribes' futures.
The solemn warning from Captain Will failed to dissuade the explorers, who continued to marshal resources for additional scouting trips into Kentucky. Daniel Boone occupied a role during this formative moment of American history harder to categorize than the politician or the military commander, though at times he served as both. Boone was a 'settler' in the most literal sense of the word. That was his true vocation—to settle areas new to him and often to the colonists. Hunter, woodsman, explorer, surveyor: these skills all helped make him this consummate settler. Though Boone generally sought peaceful coexistence with Indians, he relentlessly pushed into other people's territories, prompting conflict—thus his preoccupation with Kentucky.
Boone's early, temporary excursions into the "Land of Tomorrow" gave him a sense of the beauty and unknown dangers he could expect. On one hunting jaunt, he and fellow woodsmen read from Jonathan Swift's Gulliver's Travels, a fantasy voyage into unknown lands. The edition they read from likely contained a map of Brobdingnag, land of giants, situated by Swift somewhere in North America. The trips also led to property claims on the land by the travelers, in turn prompting a demand for surveyors to record those claims. One such team of surveyors put their lives on the line to parcel off two thousand acres below the Elk River for George Washington, then a representative to the Virginia legislature, and in two other spots recorded seven thousand acres for another legislator, Patrick Henry, who was ready to carve out a large piece of property in a place unknown to him. Washington and Henry, like other influential politicos, believed they could get rich from pushing into the territory. Joining the rolls of early surveyors was Hancock Taylor, whose nephew Zachary later became president of the United States. As he traveled in 1774, Taylor stopped to christen a spring with his daughter's nickname, Jessamine. While Taylor's team floated down the Kentucky River, Indians riddled their canoe with bullets, killing one of Taylor's men and shooting Taylor twice. As an indication of the vital importance ascribed to land claims by the settlers, Taylor was brought the survey book on his deathbed. Another surveyor "told him he ought to sign them," according to a later deposition, "and he did" before he passed away. With lives risked and lost through these explorations, actually living in Kentucky seemed about as farfetched as settling Brobdingnag.
Fanciful notions gave way to material plans as the settlers completed a series of treaties with tribes in the mid-1770s, sometimes forced onto the Indians by the military might of the settlers. For one of these negotiations, a group of land speculators had asked Boone to help draw up an agreement with the Cherokee over lands on the south side of the Kentucky River. "This I accepted," Boone later remembered, as related by his biographer. This brought Boone to an assembly of Cherokee and colonial representatives at the Watauga River, in present-day Tennessee, in the spring of 1775, shortly before the Revolutionary War began. Even when strife with Indians spread, Boone usually came off as fair-minded, poised, and hospitable, a natural ally to them. He advised another settler about how to comport himself. Approach Indians, Boone opined, "frankly and fearlessly, showing not the slightest sign of fear or trepidation. By kind acts and just treatment, keep on the friendly side of them." For Boone, philosophy doubled as strategy. Among the like-minded leaders of the Cherokee was the aged Oconostota, who had been lobbying for peace with colonists for decades.
This crowd gathered at Sycamore Shoals, named for its giant trees, on the southern bank of the Watauga. Richard Henderson was among the colonists' leaders in the venture. Henderson, thirty-nine, was an attorney and judge who had pushed back against restrictions on land expansion, especially into Kentucky, where by this point settlers had a track record of false starts and aborted explorations. Henderson saw a chance to make a fortune with a new colony. He spearheaded the weeks-long treaty negotiation. Along with the delegates, witnesses, and other attendees, the scenery filled out with wagons overflowing with goods and weapons, payment by the settlers for the Cherokee land. Covering twenty million acres in parts of what are now two states, the treaty was one of the largest land exchanges in American history. It paved the way for Boone and others to call for permanent settlement.