I am from Chicago & the police will probably not be actively searching for him. Of course if he goes back to the drug spots he might get picked up. Sadly, if he want to use he will get the money even if your mom doesn't give him any. I guess just tell him you love him and hate what drugs has done to him. I have known a few addicts over the years who chose a prison stay over the rehab route. The court ordered rehabs are very strict and if a addict doesn't want to stop it is a waste of time. They will kick you out in a second. Rest assured that he probably wont receive much prison time due to the massive overcrowding of the CookCounty court system.