It’s a fine line to walk.
Planning is required and patience is needed.
You shouldn’t crush a man to the point that he totally checks out, because then he doesn’t work for you or anyone.
If you’re careful and wear him down over a matter of years, his “fight” can be broken. Just like a dog.
He’ll still come in and punch the time clock, but he won’t ask for more than his half cup because he’ll be afraid of losing the little bit that he has.
Just keep nibbling away at his hopes and you’ll wear him down eventually.