Here is a couple of better pictures of the back.
BuckleBoy Steve Sylvia has emailed me back and forth. I sent him some more pictures and he is in contact with someone in KY that is getting some info as well. He did tell me that the Kentucky Military Academy opened in 1847 and was the only year that it was open. He did not go into what happened to it or if it merged with another school. He did also say that it had the correct loops for period. Still waiting on info from O'Donnell. If you have a good contact, could you PM it to me.
Here is a couple of better pictures of the back.