(1) to donate enough to UW to have that matter would take the kind of money the football team cares about, not the kind of money mere mortals have. They literally give a presentation to alumni about this very thing every year. (They pretend there's no donation that matters, but I've been around long enough to know that there is a threshold at which anyone gets special consideration.)
(2) No, he was never interested in ND. Too Catholic, and too private for his tastes. He doesn't love pretension...
(3) And it wouldn't have mattered because if Wisconsin was a stretch, ND was on a different planet. SFGopher is a real smart guy--smarter than me--but he didn't cover himself in glory in high school. He waited until his junior year to even try a little, and his senior year to really try. That doesn't get it done in today's college application market. No worries, he's happy where he is--and so are both of his parents.