Exactly.
He lives in Florida, but he works in Massachusetts right? So, unless I'm wrong (which is why I'm asking), doesn't he still have to pay Massachusetts state income tax? If so, that's another 5.95%.
Even if he collected $300k a year for life, he'd live comforatably, but what about his kids, grandkids, and his own parents? That's what most other people don't understand. At $300k you can't buy your parents a home, help your brother or sister out, or take care of your kids, and grandkids. You'd be able to help them all a little, or do something special for one, whereas with with $25-30 million guaranteed you could do it for everyone.