I have finally pieced together our connection to the Dent County Watsons!!
Our line is as follows:

1 Leonard B. WATSON , Sr. b: ABT 1775
+ Sarah COOKSEY b: ABT 1778
2 William Coleman WATSON b: 24 OCT 1794
+ Mary Ann GIBBONS b: ABT 1795
3 Leonard A. WATSON b: 1820
+ Nancy JACOBS b: ABT 1825
4 J. C. WATSON b: 1849
+ Anna TILLEY/TILLY
5 William Coleman WATSON b. APR 1872
+ Elizabeth BURGAN
5 Mary N. WATSON b. 1874
+ Albert M. TROUP
5 Anna WATSON b. 1881
+ Unknown FISHER
5 Laura WATSON b. 1884
One of the younger girls also married Joseph Munger. John's family all ended up in Indian Territory, now Oklahoma. William died in Wheeler County, Texas in 1932.
Does anyone have any more information on any of these, especially John C. Watson?