I'm Lucy, and I'd be happy to answer your questions today. I'm sorry to hear that this happened.
"Acquiring and paying for" means that your husband chooses the insurance, and sets up payment arrangements with the company on his own. It doesn't mean that the employer picks insurance for him, pays for it, and withholds his paychecks to cover it. If the insurance needed to be paid in full on the day he left, the contract should have said that. But either way, the law is very specific about when paychecks can be withheld, and this is not allowed. Illinois law only allows employers to make deductions from an employee's paycheck "made with the express written consent of the employee, given freely at the time the deduction is made" (emphasis mine). 820 ILCS 115/9. That last clause is key - it doesn't matter what he agreed to pay for when he started working there if he doesn't NOW agree, in writing, that they can keep his paychecks.
When there's a dispute about whether funds can be withheld, they can only withhold the money if they notify the Department of Labor that they're doing so, and then there's an investigation. The state has 30 days to investigate whether the deduction is permitted. 820 ILCS 115/14 says that, if your husband has to sue, the employer must pay his legal fees. It also says he's entitled to 2% interest on the money withheld. Each paycheck withheld is a separate misdemeanor.
One option is for your husband to show the employer those statutes, and let them know that he won't hesitate to file a complaint with the Department of Labor if they don't release his paycheck, and that he'll seek the interest and attorney's fees. He can also show them where the statute says they're actually committing a crime if they keep his money, and see if that changes their mind. The other option is to go ahead and file a Complaint as soon as the paycheck is due and not provided. There would be no reason to hire a lawyer if you have the state investigate, and you shouldn't have to go to court. There could be an informal hearing.
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