Damn, I bet you got some good stories.
A lot of it is actually pretty boring. Once they realize you aren't an authoritarian, you don't view them as a problem, you respect them and their background, and you aren't a "saltine" it is mostly playing cards and video games.
One of the kids served time for grand theft auto, kidnapping, wreckless endangerment, and fleeing to elude. Once he got comfortable, we spent hours coloring pictures he drew the night before. He talked about being in Gangster Disciple Nation. He talked about living in Chicago before his mom sent him down here to live with his grandparents. I let him talk about what he thought it meant to be a Black Man in America. The kid was smart.
So, I engaged him intellectually from the POV as someone that understood being poor and being around that life but maybe not in it. Then I spoke up for him when he was right or being mistreated by staff. The time I was assigned to be with him went quickly and without incident.
There are some cool stories, but if it got to the point it was an interesting story for people on the outside, you probably failed or they decided a bad outcome was all they would accept.