A watched pot takes forever to boil. The addict in your life will hit that proverbial wall, but probably not in an area that you are watching. If this person is an "ex" in your life, then just move on. That whole thing is between him and his HP, and your presence is not a part of it.
If you think it through to its end, I think you'll see that being denied unemployment will not be the incident that causes the addict to hit that wall.
I too get frustrated with all the enabling, especially that money is the bloodline of addiction. But I have also noticed that addicts hit that wall not because he/she runs out of enablers (the world is FULL of enablers) but because he/she runs out of energy to live that way any longer. Like the poster above, the addict in your life is not living a "cush" life - having to bum cigarettes, no computer of his own, no place of his own. Perhaps focusing on that part of it will help.
BTW, it is my understanding that one cannot qualify for unemployment if they are fired from a job. But, again, if he does not qualify for unemployment and because he is not actively seeking recovery, some other enabler (besides the Federal Government) will step up to his plate. Your job is to move on - not an easy task - but it is doable.