#1 Northeastern families with an exuberant amount of money tend to not send their kids to UConn.
#2 Growing up I was told as long as you could write your name, you could go to UConn. This is false, but my parents wanted me to go to a school with a richer prestige than UConn. When applying to colleges, UConn was my safety school. I got in, but didn't attend because I got a boat load of financial aid and scholarships from the private schools I applied to - this made it cheaper than UConn. As much of a die-hard basketball fan as I was, it was impossible to go to UConn primarily for being a "fan."
#3 New England private schools are among the best in the country. The top portion of the class rarely goes to UConn unless they get reduced tuition through scholarships, top xx of their class, etc. The private schools give more money to get the better students. Better students usually lead to better jobs and more lucrative careers, increasing their ability to donate on larger scales.
#4 Compare UConn's enrollment and endowment to Yale, Harvard, Brown, Dartmouth, etc. Even compare UConn to Fairfield, Quinnipiac, and Villanova. While UConn grads contribute, UConn lacks the graduates that can drop millions at the flip of a coin. They have them yes, but I would argue the top 1% is heavier at those schools.
#5 Big10 country the best school more often than not is the state flagship university. Michigan, Minnesota, Illinois, Indiana, etc. Talented kids go to Notre Dame or Northwestern. University of Chicago too. The best students there go to these schools. Same down south, same out west. The private schools out there aren't as good and don't poach good students. Exceptions: Stanford, BYU, Gonzaga, etc.
So when you add all these up, plus a horrible football team in the red, it makes it really difficult to generate funds at the drop of a dime. UConn started as a regional voag school while others were doing science, math, business, etc. We're playing catch up - still doing a damn good job of it though. But the regional private schools are on a whole different academic level.
Our biggest financial donor for football didn't even go to UConn. He went to our rival school and throws us peanuts because we let his son play football here. Think about that. I want Diaco gone too, but financially (in our current position) it makes a lot more sense to make an OC/DC change and pray for a bowl game vs. blowing $7 million on the same odds.