Hi Pops_Man_ have you heard of Ekhart Tolle? He and a few other spiritual teachers have said that sometimes you have to hit rock bottom to come back up. I also heard a saying the other day “I’m sorry I had to hit you so hard, but you were not listening” The Universe.
Sometimes the kindest thing to do is to step back. You know him best, if he falls you can be there to help him back up, perhaps he needs to fall to get back up.
Someone else I know, who is a recovered alcoholic and manic depressive also said that if a person doesn’t listen, you sometimes have to let them hit rock bottom before they can come back up.
If that is what happens, it is hard to watch, particularly when things seem so clear to the person watching, we are here to lean on.