The only way this delusional clown could possibly win this case is if he bribed the judge to rule in his favor. He belongs in prison or a mental institution.
I will say that for whatever reason, his lawyers always manage to be aware of some kind of technicality that prevents such a thing or close to it from ever happening. They know about it before going into trial, so if things goes south, they can just use it to make sure he doesn't actually serve time.
As far as the money he owes continuing to pile up, it will just pile up indefinitely; nobody will ever be recredited and they won't have to be, because' he'll be completely broke.