An Owen McCaffry is recorded as having been transported to the USA in the mid 1700's from Co. Fermanagh for vagrancy ie homeless. An Owen McCaffrey is found as serving under Capt Thomas Smith in the Revolutionary war for Augusta Co. Va. An Owen probably the same is found in Woodford Co Ky in the 1790 census. He was associated with a Simon McCaffrey probably a son both found in the 1800 census for Lincoln Co but written as McCafferty. This Simon acted as a scout for General Logan in taking settlers into Ky from Va and was killed by the Indians in about 1809. He had a sister Eleanor who married a Michael Kennedy who settled in Todd co. As Simon or Simeon and Owen appear as first names in the McCaffrees of Adair Co.in later generations I assume that Owen or possibly Simon was James father.The Green Co. Ky deeds for 1793-1798 lists an Owen McCaffree and a Simon McCaffrey. William b 1818 was born in Green co so there has to be a connection. Also Urban Kennedy nephew of Simon McCaffrey wrote a history of Todd CO, Ky extracts of which were published in back issues of the KY Historical Society Journal. There may be further information there on this family. There is quite a lot of speculation here but it is the best with limited documentation.