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Thank you for your question.
I would argue that this is connected to the same facts and circumstances and is barred by their agreement to the waiver (though I do see where there is a theory as how this could be connected only to the criminal case). Ultimately, I think you're right. Present the waiver to the court and move to dismiss. Whether the suit is allowed to continue is ultimately up to the judge.
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This isn't criminal, though, so I'm not sure the same expectations would apply.
His financial condition is irrelevant to whether she is entitled to a judgment. Wage garnishment can only occur after a judgment is final. You are a LONG way from that point.
I think the odds are decent. Argue that the parents signed a waiver of recovery over these same facts and events, and that they are now trying to "double dip".
I was under the impression the passenger was a minor.
They may have a case for some compensation, then. They cannot be bound by something they did not sign.
If it is holding up the probation transfer, your son may want to attempt to settle the case on a payment plan of some sort. Otherwise, you are going to have to pick apart the parent's request for compensation (as in, is what she is claiming this cost her really did for the amounts she is stating).