There was definitely correspondence between the Adjutant General's Office, War Department, with the Kentucky Confederate Pension Department ca June 12, 1916. And, there is also, an internal A. G. O. note [Capt. Penick's Co. Lt. Art. file] dated December 10, 1907, re his POW record.

This would suggest that there were two pension applications, 07' & 16'.

I checked the two counties you noted, Carlisle and Trigg and did not find one for him.

Kentucky Confederate Pensions County Search
http://www.e-archives.ky.gov/Confederate_pension.htm