I have a dilemma.

My friend Rob and I have known each other for almost 11 years, and in that time I've seen him completely destroy himself with alcohol, and a year and a half ago, he blacked out drunk at the wheel and nearly killed this poor woman when he jumped a median and collided with her head-on.

Meanwhile, I've struggled with my own addictions, so I haven't been able to help him with his problem.  I've instead been focusing on how to stay clean myself.  

So he's been in prison.  He got out several months ago on probation, but he violated his probation by drinking (and this may have happened more than once, I'm not sure), and now he's requesting that I write him a recommendation letter so that he can be released. He'll need three letters, from people that aren't related to him, to help make his case, but I'm starting to wonder if he even SHOULD be released.  His mother called me and told me about his request last week, and she said "I think he's finally seen the light," but from what I know of Rob, he hasn't seen anything except the bars on his cell.  I really fear that he'll just go back to drinking himself to death if he doesn't go straight into some kind of intensive care.

Now, I love my friend, but he's an asshole.  He's bigoted, self-absorbed, judgmental, angry, sometimes-violent, and generally childish to begin with.  He also suffers from serious emotional problems, and he's bipolar but he refuses to take medication for it.  He really is a danger to himself and others when he drinks, which he's done every minute of every day as long as I've known him, even when he's supposedly been on the wagon.  I've done my best to be patient, to not judge, and to encourage him to get help, but as with all others, he shrugs it off, or gets mad at me for it.  

I've written Rob a letter.  It's sitting here on my desk next to me.  In this letter I've asked him who I should write the recommendation letter to, and what I should tell them, but I'm apprehensive.  He belongs in long term, intensive treatment, both for his alcoholism and his psychiatric problems.  I'm afraid if he's released, he'll just do what he's always done, crawl into a bottle and hurt himself, or someone else.  I want to be a good friend to him, but I don't know if this is what's best for him.

For 11 years now, I've defended Rob to everyone I know, saying "yeah, he's an asshole, and he's a drunk, but deep down he's a good person, you just don't know him."  And that entire time, he's done nothing but fuck up over and over again.  So maybe I'm the one who doesn't know him… 

So I guess I'm asking for some advice.  Should I write this letter of recommendation for his probation, should I press him for his plan once he's released to make sure he'll do the right thing, or should I tell him that I won't help him and he deserves to be where he is?