Sounds like his identity is built around some kind of unhealthy street cult, bar room subculture environment he created for himself starting years ago.
That sort of cult stuff has been around forever. Look at the famous Manson family, with Charlie being the leader and how sick was that? Who were these women that flocked to him and sickeningly murdered for him? Or what about the Jim Jones religious cult fanatics that drank poison for him to their death.
I'm not a psychiatrist or psychologist and my mind can't possibly understand the sickness and motivations behind the behaviours of these people. It would take years of education and training for me to come close. I have to be content just knowing these are sick sick people and leave it at that. That's why you have to let go obsessing over it. imo It would be a career figuring him out completely. You need to get to a point of understanding that satisfies you enough to know that you have to let go of him. That you know you're doing the right thing and can't do anything to help him.
He may not be as bad as some of the cult leaders I've mentioned, but it could take years and years of counseling and work with no guarantees for him to deprogram all of that identity stuff enough to be reasonably functional in a normal way. And he may have issues rendering him incapable of that. Not to mention the alcohol or drug addictions, he'll have for life.
I'm sorry this is hurting you so much.