Haven't tried to look into the John Estes connection yet.
I thought by researching Wiley's wife it might lead to more clues about his father, who is unknown. Researchers across the country who are descendants of the three Estes brothers from Cumberland Co. IL show Wiley's wife as Emily. Records from Chatham Co. NC, 1805-1822, show his wife as Mary. I believe this is the same person, but don't know if Emily was a nickname or a middle name. The marriage bond from Warren Co. NC shows Wiley/Willie Estes & Milly Bagley. Milly could easily be Emily as the spelling of names was never the same. The bond is not dated so this could actually be a different Wiley. The NC records show the bond as: Wiley Estes & Milley Bagley, Warren Co., no date. The bondsman was Wm.Gwyn and the witness was M.D. Johnson. The bond is # 0001160665. Warren Co. NC was formed in 1779, so this bond was written after this.
There is at least 2 other Mildred/Milly Bagleys in Warren NC. One was the wife of a William Bagley who died in Warren Co. NC about 1806. Mildred was still alive at the time of his death, so our Wiley couldn't have been married to her. William and Mildred had a daughter by the name of Mildred/Milly Bagley. She married Rhodum/Rodam Griggs in Warren Co. the 2nd of July 1784, the bondsman was John Estes. A John Estis was also one of the signatures on the court records after William's death. Our Wiley didn't marry this Milly Bagley either. An interesting note, Rhodum & Milly name their first child, born about 1785, Wiley Griggs. Our Henry Estes, first born child of Wiley, was born about 1787, so Wiley must have been about the same age as Milly Griggs.
William Bagley had a brother by the name of Henry Bagley. Henry Bagley and wife Elizabeth bought land in Chatham Co. NC in Oct. 1777. Wiley bought land in Chatham Co. NC in Sept. 1789. Henry Bagley signs as a witness in this deed. Henry's Will was written in Dec.1801 in Chatham Co. and in it he leaves (Wiley Estis' three sons Henry, John & James Estis, ten pounds each ). Thirty pounds was a lot of money in 1801, but Henry Bagley had quite of bit property at the time of his death. Wiley names his son Henry Estes, and Henry names his first born child Melinda Bagley Estes. No one has a complete list of Henry Bagley's children because information from the 1700's is harder to find. Could our Emily/Mary be Henry Bagley's daughter? No solid proof, but there is a connection between the two families.

Later Mike...