Colonel William O’Rear (the title is probably from later militia service) was an early settler at Boonesborough, Kentucky. He had been, as a young man of 17, a Revolutionary War soldier, and following the war, went to Boonesborough as a merchant. He was a surveyor, real estate agent, merchant, town keeper and had the dubious distinction of being perhaps the first slave trader west of the Alleghenys. He later was a pioneer settler in Alabama, locating on "Orear’s Bluff" on the Black Warrior River, and finally moved to Boone County, Missouri. These two letters, preserved in his father’s desk in Virginia (see sketch No. 47), tell of his tavern venture. Madison County, Kentucky, Court Order records show "William Orear was granted license to ‘keep ordinary’ in 1786."
Boonesborough April 19th, 1786
Dr. Brother Enoch,
After my compliments to you and so forth, I hope you are will. I Received your Letter from Mr. French the 24 March & tho had been long coming I was very glad to hear you had done my business so well for I assure you I was uneasy to hear. I now must beg the favor of you to do some more business for me which is to settle an order I have given Mr. Isaac Mcferson on you for L 18..14.. of which I was ablidge to call on Charles Wickliff for in Liquor who is calld on for a return before I can raise the money & prest me for an order on you saying it would answer him well as cash as Mr. Montgomery in Domfries was to Receive it & pray Dont fail taking in the order same terms as other as I expect you can settle it with some of the other merchants in Town if not with Montgomery for produce of some kind you know who are Due me there collect what you can as I am building & just opened Tavern In This Town which I think will be one of the most capital taverns in this country. I assure you I am sometimes run hard for cash but shall soon be in a way to get my share of what is "passing" but shall not be cleverly fixt to business till I come in which I expect will be in June I am my companion as I suppose you have heard I am married I understand long before it was so -- So no more but Request you Let me hear from you before I set of in and inform me how times are there -- I Remain
Your Loving Brother Till Death Wm Orear
Boonesborough Jan. 3rd 1787
Brothers Daniel & Enoch,
I inform you I and family am well I thank God hoping you are both the same. And now must inform you my misfortunes on the road and water but suppose Mr. John Night informed you to Redstone but I assure you my journey was attended with much fatigue beside some loss I lost all my case of Gin but 2 bottles & about 12 g. of Rum By Leaking but my other goods come very safe only the Loss of about 1/2 Doz. glass tumblers & my sale Since I got out has been very slow on account of money it being very scare but my goods I never got home till the last of Nov. by being Disappointed in wagons & my Expense in coming out amounts higher than I expected -- therefore I would not Recomend you to bring foods to this country with out you could get 12 month credit & then pick you goods & if you know paper money is made by our assembly pay Dont fail to inform me the first opportunity you can get I pray give me also account how militia & military certificates pass in your parts as it may be in my power to collect a Quantity of them and also inform me Respecting Mr. Bruce whither he has paid my order as I may know whither to do his business or not. but fear not my Disappointing Carr his payment for I hope I shall be Ready for him by the time appointed & tell him I have not Collected any of his bonds yet but I have found some of the people that owe him (over). since I promised to pay shortly but for want of an assistant have not had opportunity to make much search & till Cousin John I now look for him Every Day & if either of you or Ben is coming out to see the country & wish to bring a venture of any kind I think Liquor is the surest chance for cash. So must conclude as Mr. Alvery is now waiting for me with my Respects to all brothers & sisters & Remain your Loving Brother Till Death.
Wm. Orear
I pray Do not fail informing me the particulars Requested by the first opportunity & Excuse the writing for I am in a hurry.