Wisconsin is a state--a culture--with a chip on its shoulder. It's the underdog in the Midwest, behind Illinois, Michigan, and Ohio. It's not as big, as wealthy, etc. That's built into its sports culture. The UW athletic department is actually a pretty good encapsulation of it--while the state is sports mad, it's also comfortable in its role as an underdog. Sure, they want to win championships, but they also love their identity as a scrappy bunch (and they haven't succeeded when they've tried to make it as blue-chippers).
Ohio is not the underdog. Neither is Michigan. (We'll leave Chicago--I mean Illinois--out of this for now). The cultural identity of those states and the flagship state universities is to be the big kid on the block. Period. So yeah, Wisconsin might make a run in the tournament because it is really good at winning close games, or it might lose early because it doesn't really have the talent that the highest tier teams seems to. And we Badgers will be annoyed if we don't make the Sweet 16, but not overly surprised, and we'll still love this scrappy, picked-to-finish-10th team. And who knows--maybe these Badgers will win those close games and head deep into the tournament--at this point, should that really surprise anyone?
And the Ohio State and Michigan fans will continue to be frustrated every time Wisconsin finishes higher because that's not the natural order of things (if you're from Ohio/Ohio State or Michigan/Big Blue). So a coach who consistently has top-20 finishes won't be good enough, if Wisconsin is still winning conference titles, and UM/OSU isn't.