Dolores, I’ve been in therapy for years and have reached the epiphany that my parents’ continual bailings-out kept me from growing up into the man I could have been. You absolutely did the right thing, even if he doesn’t realize it.
It’s still tough, though. I always feel bad when I tell my dog, “No!” when she’s begging for people-food at the dinner table. 
I talked to him yesterday, and he’s not mad at me at all. He said he was sorry for how he talked to me the other day (when he was in Laredo) and that everybody was fighting because they actually did get robbed. We talked about why I was not bailing him out of his messes any more and he said he understood, and that he knows he’s supposed to be a man now, and how he’s trying to be that. I asked him if he knew that I loved him, and he said of course he knew! He said he loves me, too.
We talked about his plans for the immediate future. He intends to pay me back the $50 (+$15 for “shipping.”) How he’s about to be promoted and how he intends to get his car fixed, then move to a higher-end restaurant to make more money. He tells me what it takes to be a great waiter and make good tips. I like it a lot when we can be friends and just shoot the shit, and so does he.
He is trying, and that is the main thing. I just feel guilty sometimes for the past and how I have to be now.
All is calm right now. 
Good. Don’t sabotage his trying, though, because of the guilt. It’s hard to watch him struggle, but the struggle is what will make him strong.
Did you ever hear the story about the butterfly emerging from the cocoon? A little boy, trying to help the butterfly, carefully cut away the cocoon so the butterfly wouldn’t have to struggle. Except, once the butterfly was free, it was unable to fly. The effort of fighting its way out of the cocoon helped pump the blood into its wings, and because the boy had cut away the cocoon, the butterfly did not have the chance to get its blood into its wings, and so it would never fly.
A bit on the glurge side, I know, but I think it’s appropriate.
Don’t feel guilty. You’re doing a fantastic job–and so’s your son. Best of luck to both of you! 
Not to rain on your parade, but you are probably in what is known as “The Honeymoon Phase” right now - your battle is not over, your son hasn’t changed, and you will probably have to keep on tough loving him for a while yet. Don’t get fooled by him showing you his sweet side into thinking that you can ease up on him now. Be understanding, be loving, be supportive, but don’t give him anything he hasn’t earned just because he’s being nice now. He sounds like quite the manipulator, and being nice is also part of the game plan.
Another non-parent checking in, but for what it’s worth I applaud the way you’re handling this.
I have had so many friends who were in your situation. One literally went from living in a very comfortable 4 BR home with a pool to a trailer because of the money she spent on lawyers, rehab and the like for her youngest son. It was horribly unfair to her other children and, far more than that, horribly unfair to her to be going without while working her ass off to subsidize a lifestyle better than her own. It was only when she had no more money to give that her son began to mend at all.
Another friend (the mother of my ex, though my ex is neither of the kids mentioned) literally works 60 hours a week even though she has major back and migraine problems so that she can pay the rent when her perfectly healthy piece-of-ordure 22 year spends all of his rent money going to Disney World, getting tattoos (of the Chinese characters for “Love” and “Honor” no less- he sees no irony) or buying his latest piece-of-trash girlfriend he just met a $200 watch for her birthday, or her daughter leaves her latest dysfunctional relationship and needs money to pay the pet deposits for the cats she won’t get rid of or one of them gets fired from their latest job or has to pay hundreds of dollars for a DUI, etc. etc… All of this is while his mother hasn’t so much as been to a movie (the last one she went to was with me and I paid because she of course didn’t have the money). Some while ago a $15,000 lawsuit settlement for an at work accident landed in her lap and she ended up spending every penny on those worthless kids and neither appreciated a single damned thing; both thought it was her responsibility to pay the repair bills on the cars she bought them since, after all, she’s the one who bought the cars ( :dubious: ?).
Anyway, as mad as I am at the kids of the above, I’m equally mad at the mothers for being such damned- nothing sexual meant- “total pussies” in the way they deal with their spawn. If, Og forbid, if I were ever left disabled or through no fault of my own laid off or otherwise dealt an incredible blow, I know that my mother would support me to the degree that she is able (which isn’t a lot- I’d probably move into her place and live frugally until I was on my feet again), but she also knows that I would take care of her to the greatest degree I am able including looking after her should she have to move in; in the cases of my friends, I honestly don’t think the support is reciprocal (at very least they’d make her feel like the world’s biggest leech) as they’ve been raised to be completely selfish.
Enabling is a vicious cycle and a reason that a record number of grandparents today are raising their grandchildren. You’re too young to be old and too old to have to start from scratch and I am sooooo glad you’re not underwriting your son’s failures (which is essentially what my friends are doing with theirs- they’re financing failure).