On your son's W-2, does he have a code DD in box 12 with a number? If so, this is the sum of what he and his employer paid towards his health insurance premiums. By definition, this amount is pre-tax, that is, it is removed from Wages in boxes 1, 3, and 5 before the W-2 is printed. This is why it is different from your son just writing a check.
This is what David is referring to. He also noted that the pre-tax premiums might be reported in box 14 as a Section 125 benefit.
This means that the only way you can tell if the code DD amount is actually removed from Wages is asking his employer - there is no way on the W-2 to tell; however, if they used code DD and did not removed the amount from Wages, then they filled out the W-2 wrong, according to the IRS W-2 instructions. Note that these are instructions for the employer on how to fill out the W-2, not instructions for the taxpayer who receives it.
As David notes, pre-tax amounts are not deductible in Wisconsin, but only after-tax amounts.
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