To: Mr. Hayde, re: Whitleys in Southampton County, VA: A recent autosomal DNA test that my dad took leads me to believe that your Whitley family may have originated in Smithfield, Johnston County, North Carolina.
It's a long, convoluted story, but the gist of it is this: My dad's great-great grandfather owned a store called "Whitley & Montague's" in Johnston County, North Carolina in the 1820s and 1830s. It turns out that his partner--Jesse Whitley of Johnston County, North Carolina--was his cousin. We've identified a number of autosomal DNA matches through the Whitley line, but there is one puzzling match-- a predicted 3rd to 6th cousin match on the same "Whitley" DNA segment-- whose family tree is from Southampton County, Virginia. Just googled "Whitley" and "Southampton" and found your post. Just a hunch until more proof is found, but I'll bet that your "Jessie T. Whitley" was descended from or closely related to our cousin Jesse Whitley of Johnston County, North Carolina.