Most of the UMN connected businesses have been sold or are controlled by outside Minnesota corporations. The Cargills won't touch UMN for some reason. Curt Carlson's family has stopped caring about anything that doesn't bear the patriarchs name. The Casino funded people won't give because their aggitators believe the UMN is on their land.
The anarchists and hippies from the 1960s have succeeded in turning UMN into a money-repulsing school. It's not just athletically. Look at how effed the medical school is now that they want to separate from Fairview.
UMN has been fiscally mismanaged since the 1980s when they realized cuts needed to be made and the refusal to court large endowment gifts in the 50s and 60s was a bad idea.
UMN has never understood the need to have a self-sufficiency streak because they have tried too hard to exploit the land grant status of the school, relying too heavily on state funding and the political whims of the Twin Cities.
If you go out of the metropolitan region of Minneapolis & Saint Paul and talk to people, you will find that UMN has developed a generations deep distrust and even dislike, bordering on hatred, of UMN.
The outstate region is where losing sports teams mattered because that is where state pride really sits. Losing UMN teams was just another slap in the face to rural Minnesotans. Even the rise of the MNSCU (Mankato State, Bemidji State, Saint Cloud State, et al) system has been bolstered, in part, due to successful athletic programs.
TL;DR, the hippies and beatniks took power at UMN and are effing it up. No one wants to give money and they can't unseat that mentality.