About 50 years ago, the Badger Boosters (I think that's what they were called) were constantly raising money and pouring it into the programs. The problem was, they became way too involved in the decision making at the U. Crazylegs was the AD at that time.
Granted, working with Elroy, the attendance nearly doubled at games, and they started to become more of a power. The problem was, they were always dancing around NCAA rules to get there.
Eventually, Hirsch left, and the boosters were put on a short leash, and finally removed from nearly as much inside influence.
I'm not going to go into the details of what happened.
Since then, the boosters have been strong, but never anything like they were back then, for what seems to be a fear that they could end up being like they were, and bring the entire program down.
The real key is getting individual benefactors who have super deep pockets, and are willing to dump so much money into a system that is legitimate, without strings attached. But, like Packinatl has stated repeatedly, the Badgers do not have the numbers of ultra-wealthy who can write out those 8-digit checks to support programs. Like he said, at Wisconsin, a healthy donation only gets you the "right" to pay for a decent parking space for game day.