William Bailey Smith had a varied and colorful career. He was born in 1737 or 1738 (more likely the latter year) in Prince William County, Virginia. After the formation of Fairfax County, in 1742, his father's home was in Fairfax County. Upon the death of his father, James Smith, in 1751, he inherited land in that county. His name was on record in Orange County, North Carolina, as early as 1773. Caswell County was formed from Orange in 1777.
William Bailey Smith played an important part in the early settlement of Kentucky. He also served his country by aiding in the capture of Kaskaski in 1778.
Smith was described as "a tall, rollicking, unstable bachelor, energetic and brave, but with quite a turn for embellishing the facts." 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.
The Spring of 1775 arrived, and with it the assertion of American freedom. "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.”
Richard Henderson, on Christmas Day, had advertised for settlers for Kentucky lands about to be purchased. The "Great Grant" was signed March 17, 1775, and for merchandise valued at 10,000 pounds, Henderson and his associates were declared owners of all the territory south of the Kentucky River, which comprises 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.
When Henderson had somewhat earlier become sure of his treaty, he had employed Daniel Boone to cut a road to Kentucky. 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). Boone and 30 armed and mounted axmen left on March 10, 1775, to open a trail to his destination 200 miles away.
On March 28, Henderson left Watagua and started toward the land of his dreams. His expedition included 40 mounted riflemen, quite 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 went as surveyor.
After establishment of Boonesborough, Captain William Bailey Smith was one of the defenders of the fort against attacking Indians and pursued the fleeing band. He was one of the rescuers of 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 an act was passed by the State Legislature of Virginia creating the county of Kentucky out of the territory that was later to become the State of Kentucky. The new county included the Henderson purchase, and the Proprietary Government of Transylvania ceased to exist. Boonesborough was thus a wilderness settlement of the extremest western county of the State of Virginia.
On December 1, 1778, by way of compensation, the State of Virginia granted the Henderson Company 200,000 acres of land below the mouth of Green River. The present city and county of Henderson are on this tract, where William Bailey Smith, heirs of Luttrell, and others finally settled.
Corn raised in Boonesborough the previous year was a source of profit to its inhabitants in the Spring of 1780, as there was an urgent demand for grain. It was partly to secure a supply of corn that "about the first of March brought back to the station once more the former official head and de facto Governor of Transylvania Judge Richard Henderson...He...was promoting the settlement of the Company's land on the Lower Cumberland, which was within the supposed boundary of North Carolina. ...Breadstuff was badly needed at half-starving French Lick, the future Nashville, the stock-aded nucleous of Henderson’s second colony. The corn was bought for $200.00 a bushel in Continental currency and was shipped the entire distance by water in log perogues, which made their long and crooked way down the Indian-haunted Kentucky and Ohio and up the Cumberland to French Lick. The unique little fleet was in charge of Major William Bailey Smith, whose connection with Boonesborough now ceased...”
No one knew at this time whether Virginia’s boundary line would strike the Mississippi above or below the mouth of the Ohio and "to settle doubt, that State and North Carolina sent Commissioners to survey the line westerly." Virginia Commissioners were Doctor Thomas Walker and Daniel Smith; those of North Carolina were Colonel Richard Henderson and William Bailey Smith. Their work, however, was delayed by unprecedented cold weather during the winter of 1779-80. It was called the "hard winter" and long remembered as one of great suffering.
George Rogers Clark, the western hero of the Revolution, went to Kentucky in 1772 as a surveyor. In time, he was among those who opposed Colonel Richard Henderson's Proprietary Government at Transylvania.
Clark was one of two persons selected by the Harrodsburg patriots to represent them in the Virginia Assembly. In 1776 he went as their delegate to Williamsburg. The Assembly was not in session, but he visited Governor Patrick Henry at his home and told him of the dangers to the frail, ill-equipped and undermanned Kentucky settlement because of the British and Indians of the (then) Northwest. Governor Henry heard with great interest Clark's plan to attack and conquer enemy outposts in the West to prevent their further harassment, and destruction, of the exposed Kentucky stations and to aid the colonial fight for the country's freedom.
Later, on receiving the Governor's instruction to proceed with his plan, Clark 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, according to Temple Bodley.
The territory that was referred to as the "Northwest" is what now comprises the States of Illinois, Indiana, and Ohio. The first part of Clark's mission was completed when he captured Kaskaskia on the night of July 4, 1778. The American writer Winston Churchill gives a fascinating account of that feat in his book The Crossing. Vincennes was taken the following year. There are numerous published works on these expeditions and the difficulties that followed for the reader who likes early American history.
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 near what afterwards was known as 'Smith's Valley,' 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, 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. He never married. After his death a will was presented for probation by Moses F. Smith, his nephew, the son of Peter Smith of North Carolina. Presley Smith, of Washington County, Kentucky, brother of William Bailey Smith and Peter, entered a suit in chancery claiming the will was a fraud, etc. A lengthy proceeding ensued and after Presley's death in 1819, his son W. B. Smith, Jr., pursued the court action. Moses F. Smith declared that if the will was a forgery, he was not aware of it.
There is a file of papers on this court suit in Circuit Court Equity File Box No. 17, in the Daviess County Court House at Owensboro, Kentucky. On my brief visits to Owensboro, I have had time to copy only a few of the papers. Some of the more pertinent ones from a genealogical point of view are given as Appendix C.
Although I did not get deeply enough into the file to find William Bailey Smith's will, I have been told that it is dated 1811, made in Ohio County, Kentucky, and 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, who are listed above; the children and heirs of Peter Smith, who will be named later in this text.
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 his brother Presley, who lived at a considerably greater distance in Washington County. In his later years, it is not likely that he needed personal attention and assistance in the management of his affairs that only persons close at hand could give.
 Ranck, George W., Boonesborough, John P. Morton and Company, 1901, p. 12
 Ibid., p. 1
 Ibid., p. 8
 Ibid., p. 12
 Ibid., p. 54
 Ibid., pp. 114-115
 Bodley, Temple, History of Kentucky, v. 1, 1928, p. 211
 Bodley, p. 151
 Ranck, p. 115
 Register Kentucky State Historical Society, V. 21, Certificate Book, p. 184