Not the same as James Oldham, Sr., of Hopkins County
From https://www.findagrave.com/memorial/5094280/james-davis-oldham
There were two James Oldham's, both of Virginia, one moved on to Fayette Co Indiana and his wife was Leah Stephens. He left a will in Fayette Co Indiana, Willbook B, pages 56-57, naming his wife and heirs. It was probated in 14 June 1827. He should be buried in Fayette Co Indiana where his wife Leah Stephens Oldham is buried. The James Oldham who died in Hopkins Co Kentucky had two wives, first one unknown and live in Pendelton District, SC and then moved to Morton's Gap Kentucky and married Didamy Merritt nee Todd, widow of Levi Merritt. He left many children and I descend from a son of his first marriage.
https://www.geni.com/people/James-Oldham-of-Fayette-County/4944701137900038460