TL - Great job! You handled that SO well.
You set boundaries with the phone calls. You told him you no longer wanted to spend all of your time debating the canteen and that you would think about the sweat pants and radio for a couple of weeks. Love that! And, you have decided to disengage from the girlfriend situation.
Now, don't forget to keep your radar up. Remember that your difficult child wanted something from you (sweats, radio, and canteen $, etc.) during this phone call. As he senses that you are setting firmer boundaries, he will figure out that he needs to be more convincing to get what he wants. My JT is very manipulative and great at telling people what they want to hear in order to get what he wants. Many times, I was duped into thinking he was making better choices, only to realize much later, in hindsight, that he was lying and manipulating me.
You did ask him about his girlfriend's pregnancy. The fact that he knows you cared about it can be used against you. Don't be surprised if future tactics by him involve this situation.
If I am not mistaken, your difficult child has been in jail before, right? If this is not his first time, and this is just my humble opinion, I would not give him the radio, sweat pants, or canteen dollars at any point. Those items would make him more comfortable, and he needs to be very uncomfortable, fully experiencing the consequences of his own actions. The fact that so much of his energy remains focused on getting stuff for himself vs getting serious about recovery from his substance abuse and turning his life around, speaks volumes.
I realize that the logic in giving him those things is that they might help him on his healing path. I get that. When our difficult child ended up in jail (first offense), we bailed him out, because we didn't want him to lose his very good job. We thought losing his job would make everything so much worse, and jail was bad enough. We thought that just being in jail (for distribution of alcohol to minors and also underage drinking) would be a wake-up call for him and that he wouldn't make the same mistakes again. But here we are, just a few months later, and JT is drinking and causing all sorts of drama. He still has his job, but his substance abuse hasn't changed. If he ever ends up in jail again, we will not be bailing him out, visiting, or doing anything in any way to spare him the consequences of his actions. Nothing. No matter what he loses or how uncomfortable it is for him. HE needs to experience the full consequences of his choices. When his problems truly become his problems and he is not rescued from consequences, he is much more likely to take action to positively change his situation.
The way you handled this situation is fantastic. You are so smart and strong. I hope your son makes better choices going forward. Keep us posted.