Looking to help a friend

Hi everyone, I apologize if this is not the correct section of the forum but I was unsure. I am looking to help a good friend who is going to be prison for a long time. He suffers from some rather palpable mental issues including addiction, depression and anger, among other things. I am concerned for him on a number of levels because of these things as well as the fact that he has not yet been sentenced (he's been in a pre-trial unit for almost two years now) so I am unsure of exactly what is going to happen. I am writing him a letter and just looking for some kind of references or advice that may be helpful. I *believe* he is allowed to have books and so any suggestions on authors would also be appreciated. To be honest I am not even sure exactly what it is that I am looking for here. I'm just having a hard time with the whole thing, I suppose. I just want to be helpful and supportive. What do you say to someone whom you're not really sure when/if you will even see again?

An ex of mine was in prison for a year and a half (he's still there, we're just no longer together or in contact) and we spoke pretty regularly. I spent hundreds of dollars adding money to his account for phone calls, but other than that he could call me collect if he wanted to. Letters seemed to be a huge help and relief to him, though. Just having contact with someone he cared about helped him get through his days. I think if you send him letters, it won't much matter what you say (just be careful not to include anything the guards will deem 'inappropriate' or he will not receive it) because the fact that you bothered to write will show him at least someone cares, hopefully.

How well do you know the person? I say dont come off as cliche by getting him some self-help book on beating addiction if he's locked up for drug related crimes. Get them something they would like and be interested in, something for them to get into. Even a lame hobby could be a good thing. A book? I'm tempted to say The Count of Monte Cristo, but that may be a poor choice... Moby Dick? There are some really good books out there, everyone should at least try a few.

It is hard when we lose a friend. I know you will be able to visit him but it will never be the same. However, if he has done something bad and must go to a prison well, it will be a lesson for him. Of course, I am not judging. It is nice that you want to be supportive and the best way is to stay in contact and visit him as often as possible. Regarding the books, well, you can suggest him to read some books about how to overcome an addiction but also some other good books. I personally would suggest Stephen King, Paulo Coelho, etc.