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He cannot recover restitution that you have already paid. If you bring evidence from the court case that you paid full restitution, the judge should dismiss the $44,200 part of the claim. Your former employer can still claim punitive damages, which tend to be based on your ability to pay and the wrongfulness of your conduct. That's not likely to come anywhere near close to $300,000 unless you are independently wealthy. To get an additional $300,000 in damages, he'd have to establish some causal link between the money you took and later business losses. You're not liable for ALL business losses that occurred. He has the burden of proving he's out the amounts he's asking for due to your behavior. He's not out anything you've repaid. If he doesn't have proof of the rest, the judge can't make you pay.
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