Jake/River
I apologize I didn't even think about T being confused for Therapist. I'm really weary about using the names, since it's not my secret to tell. The little won't be identified as him so I think it's ok to refer to him as Tommy.
The brain tumor is actually more around his brain and ear than actually part of that. So I don't think it's part of any D.I.D. stuff. Plus he's had like 30 surgeries like this in his life around his ear, so if it has made a difference, it's nothing that has recently changed. It's mainly just the fact that he is taking pain meds which weakens my SOs (Jd's) ability to stop shifting. (It seems weird to only refer to the core as my SO, but all except the little are my SOs, I'm marrying all 6.

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I like the ideas you presented with art therapy and such. I'll keep that in mind when we are in person and he is out.
The prison is not giving him help with counseling or therapy except the bare minimum necessary which is not even weekly and usually not more than 20 minutes. They just think he's a troublemaker/liar who's trying to con them. They don't believe in the D.I.D. There is no doubt he has it, because of my interactions with each of them. His sister was diagnosed and has confirmed it as well. He's just the type to never admit it. He didn't even know his sister knew until I told him about a week ago. And he trusts her big time. So he never tried to get it diagnosed. He didn't want to admit it.
I guess my biggest concern is how to approach him being there. Jd has known about 5 of his alters since he was a kid. I think there are 2 more that haven't come out yet that he isn't aware of besides Tommy from what I've heard his sister tell me about the past. But Jd is not comfortable with the others fronting. He has not figured out how to stay present with any of them, so it's all scary for him. I want to acknowledge Tommy because he did make the move to contact me. There is a reason he felt ok talking to me and I don't want to ignore him (of course if he's out I wouldn't) but in context of when he's not fronting. For example. I sent 6 birthday cards, one to each I know. Well it seemed important to me to send a card to Tommy now that I know him as well. I don't even know if he can read, but I don't want him to feel excluded. How aware do little's tend to be when they aren't fronting? I'm stuck between wanting to give him attention but not wanting to draw him out in that setting either. If that makes any sense what I just rambled.

In the future should I address him in letters that I address everyone else in? Or when I send everyone a card for a special occasion? Jd is very concerned about Tommy being active.
Ultimately my goal is to gain Tommy's trust, to help him feel safe, accepted and loved. To encourage him to have his feelings, and to be able to tell me things like when he said he doesn't like me without any judgement or critique. (When he said that to me I just said, It's ok that he doesn't like people and "I hope we can be friends").
I am very appreciative of your comments. Thank You!