When I went to the U in the mid-1990's, Madison was the same distance from Chicago as it is today. Wisconsin had gone nearly 50 YEARS without an NCAA tournament berth. It's not just that they sucked; they were irrelevant. The U's basketball history, in contrast, was peppered with some really good teams and really good players, followed by scandal that knocked the program back down...a cycle that had repeated itself several times. The fan support was outstanding...there was nothing like the barn rocking on a cold February afternoon. At that time, nobody in their right mind would describe Wisconsin as having more potential than Minnesota.
Minnesota and Wisconsin have similar populations (WI 20th, MN 21st or thereabouts), and their AAU output is similar, but Wisconsin not only had to contend with a putrid history, but also the fact that they weren't even the #1 D1 basketball program in their own state. It would be as if the U of M were in Duluth and there were some program like Marquette in Minneapolis. Not to mention the fact that other D1 bb programs further siphon some (albeit minor) fanbase in a few of Wisconsin's other decent-sized cities.