Jim,
In John Livingston's book "Such a Foe as Livingston", he lists both D.M. Condray and B.F. Carter as members of Livingston's Battalion, which was called the Cherokee Spikes. Livingston was often in cooperation with Watie and at times was to report to Watie or Cooper and told to look to Watie for supplies. In spring and summer 1863, there were 75 men of Adair's Regt (2nd Cherokee Mtd Vols) from companies C and H on detached service with Livingston. I find no record on Condray or Carter in Bryan's Battalion (1st Battalion Cherokee Partisan Rangers), Adair's 2nd Cherokee (which was created from Bryan's Battalion), or the 1st Cherokee Mtd Vols (Watie's Regt). It could be Carter's Company was part of one of Watie's Regts, perhaps temporarily assigned. The records are very scant, especially after June 30, 1863. The organizations were very "fluid" and it could be that detachments of various units, partisans, and guerrillas were operating together as the opportunity or need arose. From time to time, I run across men who claim to have been in one of the Cherokee Regts on pension applications and such that never appear on the rosters. It is unclear whether they actually served with the Cherokee or had some other motivation, such as not admitting they were with Quantrill. They may have not been enrolled in an official Confederate unit and picked Watie's Regt as one that was well known and did NOT have a bad reputation like Quantrill and others. I did find an 1864 POW record for a B.F. Carter, captured in Missouri and claiming to be a conscript. I also found in the citizen files, records of Quarter Master A.S. Cabell paying a D.M. Condray for services as an assistant wagon master in about March through May 1863, signed at Bonham TX.

My best guess is that Condray and Carter were guerrillas in Missouri that may have acted in conjuction with Watie's Cherokee regiments. I presume Condray picked the 1st Cherokee as the official unit for his medical discharge since there was no question it was a fully official Confederate organization. He may have been with Livingston and attached to Watie's command in 1862 in southwest Missouri or at other times. In June of 1863, Cooper's main encampment was at Honey Springs in the Creek Nation, just west of the Cherokee boundary so if he did enroll with Watie's 1st Cherokee at that time he may have been in either the Creek or Cherokee Nations. Livingston was in killed at Stockton MO in July 1863.

I'd be interested to know if you run across other info on Condray or Carter.

Ken