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The most serious crime is the resisting. If he forcibly resisted, he will probably go to jail for a little while. The possession charge could result in a small amount of time too. The fact that he just got off of parole is not going to make things any better for him.
Unltimately, it depends on the prosector and judge on his case, but there is a good chance he will get a little time, though probably not more than a couple months.
I should say, this is all a guesstimation... the actual facts and charges will make the answer vary wildly.
Would a letter to the States attorney help in any way. He is a junkie and in a very bad place and I know he needs the jail time to detox. I know this sounds crazy, but I fear if he does not go to jail he will harm himself and others. This is a small town and the states attorney is very friendly and it is easy to talk to him. Jo Daviess county.
You want him to go to jail? Since you are not a victim in any of his crimes, your input probably won't carry any weight. That said, it can't hurt.
If the victims ask for jail, that is more compelling.