Chicken Dilemma. What Would You Do?

I know the government is in the middle of a crisis, but can we talk about me?  I need your advice.

Three young men in my town were recently arrested for breaking into cars and vandalizing public property. All are legal adults and were booked on felony charges

My dilemma is that I know one of the three and am trying to decide the best way to help him. I'll call him "J" to protect his privacy.   He grew up in the neighborhood, was a good friend  to my eldest son, and spent a lot of Saturday nights sleeping over at our house.  

I won't bore you with every detail of his background, but suffice it to say that the one person who loved and nurtured him got very sick and died.  Her illness and subsequent death sent his life into a tail spin.  He moved away for a time, but came back once he turned 18.  His situation has been precarious.  He has little support, emotionally or financially, and is, most likely,  suffering from depression.  It's hard to tell.  A lot of  his emotions are trapped on the inside and his affect is flatter than a six-month-old glass of coke.

After a rough start, he seemed to be on the right track, earning a GED in record time, participating in a work program, and eventually transitioning into a part-time job. His goals were to get his license, save some money, and join the military.  He was living with another family that I do not know, but he seemed grateful to have a place to stay.  He came over several times a week, for awhile, and I would feed him, encourage him and try to get him to talk.  When I remember the meme of the kitten hanging on to a ledge by the nails, with the caption, "Hang In There, Baby",  I think of J.

I asked my son,  after the neighborhood gossip made it around to our house, what he thought J was thinking to put himself in that situation. My son's response,  effectively, was that he would never put himself in a position to fall out of favor within a peer group. That makes sense,  I guess, when you consider what it means to be alone. Most of us prefer the pack.  It's the way we are made.

I texted and called J when I found out about his situation.  I wasn't sure what I could do, but I did want to make myself available to him.  When he didn't respond,  I did a search online, which confirmed that he was still being held at the intake center. 

I could probably scrape together enough bail money to get him out of jail.  I'm aware that it is money I would most likely never see again, and I could live with that.  My dilemma is that helping with his release would only solve his most immediate problem.  If released, he will need a place to live, a job, and emotional support, as well as practical support.  My husband is not willing to bring him into our home and I respect that.  I also feel I do not have the tools, time or resources necessary to help him find  his footing, and there does not seem to be anyone else in his life who is willing to take on that role.  Without some hefty support from somewhere, he will most likely end up back in prison, possibly worse off for my assistance.

If I bail him out, am I hurting more than I'm helping?  Are there services and people within the system who can help him more than I can outside of the system.  Is the system set up to rehabilitate young adults who are not hardened criminals, or does it just process every criminal the same way?

What would you do?  Is there anyone out there who has experience  with these sorts of cases and can speak to what is likely to happen to him next or how I can best support him?  I am not comfortable with the notion of no action, but I'd like to proceed cautiously.

I am a Chicken, after all.  Thank you for reading.  I will be resuming my usual nonsense after this short reality break.

Chicken out