I have never had any problems pilling my cats alone so this may sound ridiculous to those of you with experience with more difficult cats but I'll give it a shot anyway (I only thought of it because I've been having my SO hold Moon down while I apply his frontline because that has been a challenge alone).

So...what about getting help? Have one person hold his front paws and another hold the back paws and then you can open his mouth and pill him?