James Woodsmall died December 19, 1808. His eldest son, George Lasley Woodsmall, Sr., had built a separate cabin for himself on his father’s Simpson’s Creek farm before his father died. He inherited the farm as the oldest male sibling and lived there until he and his siblings sold the family farm to Edmond Cotton May 10, 1817 and he moved to Shelby Co. Edmond Cotton was Margaret Woodsmall’s uncle-in-law (her husband Thomas Halbert, Jr.’s mother Sarah’s brother).
The first indication of a Woodsmall link to slavery is found in a January 20, 1813 Bill of Sale for a 28 year old male slave named Baccus who was sold for $400 to John Newland by George Lasley Woodsmall, Sr., together with two partners. It is not clear whether this slave was owned by the three partners for work or if this was a speculative venture. The 1820 Kentucky census for Shelby Co., where he moved after selling the Simpson’s Creek farm, confirms that, in 1820, George Lasley Woodsmall, Sr. did not own any slaves. Nevertheless, his son, George Lasley Woodsmall, Jr. adopted a pro-slavery attitude, one that was shared by his wife, Tabitha McKenzie’s family, who were from Henry Co., Kentucky. The family of George Lasley Woodsmall, Sr. though, became sharply and totally divided on the issue of slavery.