[Shinertx]

I am new to this board but there seems to be a wealth of knowledge here so looking forward to any help that can be given.
I have an older shih tzu that came to me as a stray. He does not appear to have been well taken care of as a pup, his teeth are bad, his eyes have not been taken care, he was not neutered, and his hair was horribly matted when he was found. Fast forward a few years and we are now dealing with increasing health problems.
Max is currently on 8 pills a day. Initially we were giving them to him by breaking up treats and just squeezing them together. He would suck the treats down so quickly that he never noticed the pills. However he has gotten wise to that and now spits them both out and just picks up the treat.
I have tried the manual method and holding his mouth closed but his airway is narrow and he starts to choke very easily. Also he is able to spit them up several minutes after he should have already swallowed them.
We have also tried crushing them and mixing them with soft foods but he has figured that out and just sort of picks at the food. By the time he finishes the whole thing it is time for the next dose.
Sorry for the long post but would appreciate any help.
Thanks Jennifer