I'm just curious how the hell they hope to sentence him to prison if he's already escaped it more than four thousand times...
I'm pretty sure at that point they skip prison, and start sentencing him to death.
Which segues into my idea: more colourful prison sentences at M or C (still only death at C+ of course). It's kind of hard to come up with stuff that we could actually implement, but I would love to see conservative indoctrination at C or C+ free speech and torture for example. Your second in command gets arrested and next thing you know he's part of the CCS, with all the skills he had before, or when you break him out he becomes a mole (so any safehouse he's in gets raided at a lower level of heat). Obviously the key stat would be what "fortitude" = heart - wisdom, with people having negative fortitude breaking pretty much instantly and people with a fortitude of 8 or more basically never breaking.
Currently, an underling being arrested is basically just an opportunity to break them out of court or the prison. If they have a low heart they have a chance to rat you out and you get a racketeering charge. Oh no, now my founder will be
double arrested. I think having to monitor your prison escapees for conservative infection would make arrest a little more meaningful. Plus, trying to salvage a raid on the nuclear plant after your strongest fighter triggers the alarm and starts shooting your team would just be awesome.