Henderson’s Transylvania Purchase


Every tree has to have a rock star in it; someone who defies reality; seems other worldly, Orwellian by nature; a regular sort of Forrest Gump, but literally living in the forest. Someone famous has to be living a little closer than the 6 degrees of separation allowed by Kevin Bacon. Let me introduce you to Uncle Bailey.  Here’s how you too can find him:  Simply Google “William Bailey Smith and Daniel Boone” together in one search. Those are the key words.  And Bingo… There’s Uncle Bailey, son of our James Smith of Bull Run. And what is he doing in those first few Google hits we have: Working with Daniel Boone, Going up against Blackfish, fighting for Boonesborough, and saving Boone’s daughter (Jemima) from captivity at the hands of Natives had kidnapper her. Not bad for starters. There’s more.

William Bailey Smith (1737-1811) is my 5th Great Uncle and brother to Peter of Round Hill. He was born on Bull Run, the son of James and Elizabeth Taylor Smith, and grandson of Peter of Yeocomico (d.1741). Bailey, as he was known, carried the surname of his grandmother, Mary Bailey. The Bailey name was well established in the Virginia Colony. It is found in the early records of Jamestown, Westmoreland and beyond. Her ancestors are identified in our tree and landmarks along the Virginia highways reference their homestead.

Bailey remained single for his entire life and there is no evidence that he was a lothario or father of unwanted children. He lived his life in the vein of the famous Jamestown hero, Captain John Smith. That is to say, Bailey was married to adventure and exploration. While Captain John Smith, no known relation, was married to the sea, Bailey was wedded to the wilderness beyond the Blue Ridge Mountains. His adventures are well documented and it is possible to develop an historically accurate portrait of the man and his contribution to the growth of America from Coastal Colony to inland empire.

The work of Bailey Smith brought him into close professional and personal contact with Daniel Boone in the construction of the Wilderness Road, the ‘peace treaties’ of Wautauga, the skirmishes and battles of the infamous “Indian Wars,” and the development of frontier fortresses including Boonesborough, KY. Covering all of that in a thumbnail sketch will be difficult, but worth a shot.

Upon the death of his father, James Smith, in 1751, Bailey inherited land in that county. Deeds also reveal that he joined his brother Peter Smith in Caswell County, North Carolina. His name is on record in Orange County from which Caswell was organized in 1777. Bailey and Peter were part of a great migration of pioneers who settled into the rich soils and forests of the Piedmont in the wake of the American Independence movement. The energy that propelled Bailey’s Uncle Thomas Smith and George Mason IV forward in their search for liberties in Colonial Virginia drove Bailey Smith’s indomitable thirst for opening up the frontier to settlement.

But, first things first. The Spring of 1775 arrived with a clamor for American freedom and independence.

“The hour had struck for the permanent settlement of Kentucky and in widely separated regions the hearts of unconscious instruments of fate had been fired for the work. But in no American colony was the interest in that distant forest-land keener than in North Carolina and in no place in North Carolina was it so conspicuous as in the…little frontier settlement of Watauga in what is now East Tennessee.”

Wautauga was a breakaway place on the North American continent. A handful of Caucasians knew what was beyond the crest of the Blue Ridge mountains. Long hunters who had traversed the hills knew that the hills seemed to go on forever. It was known that the Ohio River flowed West and that the Great River to be known as the Mississippi sort of ran north south into the Gulf of Mexico. The Natives knew the area well but the white guys had a sketchy notion as to what was out there in terms of resources and land. Some of the white guys had studied the growth of the American colonies and understood that friends of the British monarch could score a patent, a large deed of land, and then sell that land off in parcels and become all the more wealthy.

These same white guys saw the American Revolution as an opportunity for a land grab, a stab at establishing a small American country to the west of the colonies, independent of England, independent of Virginia and North Carolina. Kind of like Holland was to France, Wautauga could be to North Carolina and Virginia, a small nation off to one side of a larger nation.

The first permanent white settler in what is now Tennessee was a guy named William Bean, who settled in 1769 on Boone’s Creek, near where it flowed into the Watauga River. Communities like Nolichucky, Carter’s Valley, and North Holston sprouted up in places where a river might afford a mill, or a crossroad might be found. Folks arrived via the Shenandoah Valley through western Virginia. Others, victims of the failed Regulator Rebellion (1771) in North Carolina came into Wautauga from the East, finding gaps in the mountains that would allow a cart, wagon or simple man on horseback.

Folks in these hill country settlements believed they were in Virginia. They were a bit off in their estimate and it created a problem for the British, Virginia and the Cherokee Indian. A survey revealed that only North Holston was in Virginia. The remainder of the settlement was part of North Carolina’s western claims— land guaranteed to the Cherokee Nation. The British told the Wautauga settlers to pick up their home furnishings and head north of North Holston and let the Cherokee have the land to which they had been promised.

Settlers then did what settlers did in those days when threatened. Expecting a battle from either the British or the Cherokee they refused to budge. They moved into the safer confines of the Watauga settlement, behind the timber palisades that were the earmark of colonial settlements from Jamestown and Plimouth Colony right into Kentucky. The Wautauga leadership approached the Cherokee with a request to lease land along the Watauga River. The Cherokee agreed. The Wautagans were elated. Their problems were solved. The Brits were not happy. Insubordination was becoming all too commonplace among the colonists. The British Proclamation of 1763 outlawed the purchase of Native land by anyone other than the British government.

The Wataugans established what amounted to the first white, autonomous bureaucracy in the British colonies. The Watauga Association (1772) cloned the Virginia legal system replete with commissioners, court cases, legal documents, and land titles. The settlers focused on the practical needs of routine government. The pattern reminds me of Swallowfield, England and the Articles of 1591. Like the authors in Swallowfield, the Wautaugans did not claim independence from Great Britain. They didn’t really have to. Their physical position on earth was far removed from any white government out there. At this point in time they had more in common with the Cherokee.

In 1775 the Watauga settlement was the site of a most remarkable real estate transaction: the Transylvania Purchase. For several days in mid-March, Richard Henderson of North Carolina negotiated with leaders of the Cherokee Nation. William Bailey Smith is recorded as being at the table and playing a role in the negotiation process. He eventually secured an agreement by which the Cherokee exchanged their claim to all of the Cumberland River Valley and most of Kentucky in exchange for 10,000 pounds of trade goods. Again, this reminds me of our great grandfather Van Couwenhoven’s first recorded purchase of land from the tribes of the First Nation on Manhattan Island in 1635.

Henderson’s Transylvania Purchase

Henderson and his associates were declared owners of all the territory south of the Kentucky River, which comprised more than one-half of the present State of Kentucky. The Cherokee Indians, on that date, deeded the land to Henderson and Company. William Bailey Smith was among those who witnessed the transaction.This purchase, referred to as the Transylvania Purchase, was nullified by both Virginia and North Carolina, who were still holding to the notion that the land was Cherokee. Colonial leaders on the Atlantic coast, focusing on a war with Britain, did not wish to stir up a battle on the western edge of the colony.

The purchase created some serious negative vibes within the Cherokee Nation. A militant faction of the tribe, under the break away leadership of the Chief’s son, Dragging Canoe, broke with their elders and sought to reverse the sale and maintain control of their hunting lands. This growing faction aligned with the British during the American Revolution and raised hell with American war efforts. These activities also drew our Bailey Smith into the history books as a frontier soldier and legitimate mountain man.

The threat of Cherokee attack was real and Wataugans appealed to both Virginia and North Carolina for protection. North Carolina agreed and created the Washington District to include all Carolina lands west of the Blue Ridge into lands as far as the eye can see. The Cherokee attacked in 1776. The Wataugan’s retreated to their fort and withstood the siege. In 1777 Washington District became Washington County, and the Wataugans gave up any urge for independence. The Association was no longer necessary.

The Wataugans did play one more significant role in the American Revolution. Known as the “Overmountain Men” because they lived beyond the Blue Ridge, they gathered at the Sycamore Shoals of the Watauga River. They crossed over the mountains and attacked and defeated British Colonel Patrick Ferguson at the Battle of King’s Mountain in 1780.It was a battle which Jefferson referred to as thee Turning Point in the war with Britain. We had relatives on King’s Mountain that day. One of them, a Whittington great grandfather, died in the bloody forest that day, in the arms of his son, Phillip Williams.

Bailey Smith’s role in the Transylvania Purchase was one aspect of his work for Henderson. On Christmas Day of 1775 Henderson’s pamphlets circulated, advertising for “settlers for Kentucky lands about to be purchased.” Henderson and Boone had already agreed that the first settlement should be made at the mouth of Otter Creek on the Kentucky River (the settlement was later known as Boonesborough). With all of that land in the ‘Caintuck hills’ at his disposal, Henderson was eager to open a road and move pioneers into his domain. This was the model for how land speculators operated.

Smith surveyed the land and organized the route. On March 10, 1775, Boone and Smith and 30 armed and mounted Scotch-Irish axmen began felling trees, turning Native hunting trails into horse paths wide enough for wagons, and early versions of the Suburu, heading for a destination 200 miles away.

On March 28, Henderson pulled a move that would catch Boone off guard. He left Watauga and started toward the land of his dreams. His expedition included 40 mounted riflemen, including a number of Negro slaves, 40 pack horses, a train of wagons loaded with provisions, ammunition, material for making gun powder, seed corn, garden seed, a drove of bees, etc. Henderson was accompanied by four other members of his Company: his brother Samuel, John Luttrell, and the Harts. William Bailey Smith was relieved of his work on the front edge of the pathway and was called upon to accompany Henderson as a surveyor. Henderson expected Smith to refine every aspect of the trail as they moved forward, insuring that the preliminary work conducted by Boone’s contingent was now turned into a highway wide enough for wagon travel.

Once the road was opened and Boonesborough established, Bailey Smith continued his work for Henderson. As a military Captain, Smith was one of those chiefly responsible for the defense of the Boonesborough fort against Indian and possible British attack. He was one of those who rescued Jemima Boone (Daniel’s daughter) and the Callaway girls when they were captured by Indians. At different times Boone, Smith, and Richard Callaway negotiated with the Indians.

On December 7 the State of Virginia designated Kentucky as a county within the state. The new county included Henderson’s Transylvania purchase. Boonesborough was thus a wilderness settlement at the extreme west end of Virginia.[5] Henderson and his investors were compensated for their loss with 200,000 acres of land below the mouth of Green River. The present city and county of Henderson are on this tract, and it was here that William Bailey Smith, heirs of Luttrell, and others finally settled.

Smiths work at Boonesborough came to an end, but he continued in the employ of Henderson who was now focused on developing a kingdom in what is today Tennessee. In the Spring of 1780, food and grain was desperately needed at the half-starving community of French Lick, present day Nashville. Henderson was shipping foodstuff the entire distance by water in log barges traveling along the Kentucky and Ohio Rivers and up the Cumberland to French Lick. The fleet was in the charge of now Major William Bailey Smith.

Smith’s Role in Determining the Virginia and North Carolina State Line

No one knew at the time whether Virginia’s boundary line would strike the Mississippi above or below the mouth of the Ohio. Confusion in the settlement of Watauga was just one example of problems that evolved as pioneers pushed westward into the hills of Kentucky and Tennessee. To put the issues to rest, both states sent Commissioners to survey the line to the west. Virginia Commissioners were Doctor Thomas Walker and Daniel Smith; those of North Carolina were Colonel Richard Henderson and William Bailey Smith. The Daniel Smith representing Virginia was not our Daniel Smith, son of Thomas Smith, as I originally thought. Thomas Walker may be descended from the Walker family of Westmoreland, neighbors and relations of Peter Smith.

William Bailey Smith and George Rogers Clark, the western hero of the Revolution

Clark arrived in Kentucky in 1772 as a surveyor. He was among those opposed to Colonel Henderson’s Proprietary Government at Transylvania. Clark had visions of his own for the development of the region. He understood the important role these new frontier lands would play in the growth of America. In 1776, as a delegate in the Virginia Assembly, Clark strongly urged Governor Patrick Henry to be mindful of the need to protect the backside of the American front in the war with England. Kentucky settlements were frail, ill-equipped, undermanned and vulnerable to British and Indians in the Northwest Territory. Governor Henry heard Clark’s plan of attack and authorized the raising of an army to attack remote British forts and protect the western front.

Clark received permission to proceed with his plan and chose the captains and lieutenants for his expedition and began recruiting. His diary says:

[January 2] “Appointed W. B. Smith major. He is to receive 200 men [on the Holston] and meet me in Kentucky the last of March.” “3. Advance Major Smith 150 pounds for said purpose.”

These actions are on record in the Illinois Historical Collection, V. 8, pp. 36-37.

Clark wanted to raise 400 troops for his Illinois campaign and he hoped Smith alone would pull 200 soldiers out of the Watauga area. Smith’s efforts were made difficult by a number of competing issues. The locals were more concerned about defending their homes in Appalachia and did not want to leave their families vulnerable while they went off to protect Kentucky pioneers. The federal government (Continental Army) was competing with Virginia state militia efforts and paying more for soldiers. Smith did not reach his goal of 200 troops and his force, once it headed west, was running behind schedule, throwing off the timing of the entire campaign. Clark had to make adjustments in his plans. When Smith’s troops arrived in western Kentucky they heard Clark explain the nature of the task before them. Smith had been ordered by Clark to keep the invasion a secret. The Watauga men had no idea they were part of an invasion force. They expected to protect Kentucky villages from marauding bands of Indians. Many of them deserted in the dark of night and headed back to North Holston. Those who remained helped George Rogers Clark secure Forts Kaskaskia and Vincennes.

The Virginia Magazine of History, V. 15, p. 88, provides evidence that Smith gave military service in Kentucky prior to the “Northwest” expedition: “1777, December 11. Smith, Captain William Bailey, for pay for his Company of Kentucky Militia, p. Pay and Cert., 878. 7. 7.”

William Bailey Smith “finally settled about 16 miles from the site of the present city of Henderson, Kentucky, on a tract of land which he received from John Luttrell, of the Transylvania Company, in payment for his services. His residence was known as ‘Smith’s Valley,’ at the mouth of Green River.”

He received a grant of 400 acres of land in Ohio County, Kentucky, on February 19, 1780. He also claimed for his brother Presley Smith a preemption of 1,000 acres “lying on Panther Creek Waters of Green River below the land of William Bailey Smith on the said creek” and “a preemption of 1,000 acres of land at State prices…lying on Panther Creek adjoining the lands of Presley Smith” for Peter Smith, presumably the brother of Presley and William Bailey Smith. These preemptions were granted “on account of marking and improving the same in the year 1776.” Nancy Smith Boggess, sister of the Smith men, made an entry for 1,000 acres on Clifty Creek in January 1783.

William Bailey Smith died October 19, 1818, in Daviess County, Kentucky. Upon his death a will dated 1811, made in Ohio County, Kentucky was presented for probation by Moses F. Smith, his nephew, the son of Peter Smith of Caswell County, North Carolina. Presley Smith, of Washington County, Kentucky, brother of William Bailey Smith and Peter Smith of Caswell, entered a suit in chancery claiming the will submitted by his nephew Moses, was a fraud. A lengthy proceeding ensued and after Presley’s death in 1819, Presley’s son W. B. Smith, Jr., kept the case alive in court. Moses F. Smith denied any charges of forgery. [Per the work of Pearl Smith, the paperwork for this case is found in Circuit Court Equity File Box No. 17, in the Daviess County Court House at Owensboro, Kentucky. Some of the more pertinent ones from a genealogical point of view are given as Appendix C.]

Presley Smith’s concern about Bailey’s will relates to the nature of the gifts: the will bequeaths $500 to nephew James Simpson Smith; $100 to William Wigginton Smith (both sons of William Bailey’s brother Peter), old slave Sinah to be set free; and balance of estate to Moses Smith. Witnesses: Richard Taylor and Jacob Shaw. Mentioned in papers pertaining to the suit were Nancy Smith Boggess and her children.

Since William Bailey Smith and his nephew Moses F. Smith both lived in Daviess County, and nephews William W. and James S. Smith lived nearby in Muhlenberg County, it seems likely that they had more contact with him than did Bailey’s brother Presley, who lived at a considerably greater distance in Washington County.

Smith was described as “a tall, rollicking, unstable bachelor, energetic and brave, but with quite a turn for embellishing the facts.”[1] Smith’s positive characteristics, together with the fact that he was unmarried, seem to be those of one who might seek adventure in the settling of a wilderness as the frontier moved westward.