BTW, apparently this guy owes the IRS about $5 million. The entire $8 million (if that’s the real figure) would be subject to income tax at 37%, which would leave him with less than the $5 needed to pay off the IRS. Of course, the details matter, but that wouldn’t get him completely out of hot water, just mostly. See how the evil rich control you...they give you enough to live decently, for a while, and not one penny more.
If they do, then he has a windfall. Not necessarily baked into the cake - he apparently did not pay taxes that he withheld from the paychecks of his employees - that is a BIG, HUGE, no-no. The IRS will generally waive (or greatly lower) penalties if it is your first time, AND if it appears that you weren’t trying to cheat them. Withholding taxes are like a trust fund - and as the “trustee” you are held to a very high standard.
Also, part of bargaining away a huge liability is the lack of resources to pay - but he just got $8 million.