You're looking at it from just a pure 18 basketball games or so per year perspective. Is there a line of people waiting to donate tens of millions of dollars for a DePaul basketball arena only? Maybe not. Is there a line of people waiting to donate tens of millions of dollars for an arena that's going to be attached to McCormick Place so that his/her name becomes immortal in Chicago or, if you're a corporation, curry a TON of favor for the pet project of the Mayor (in a city where the Mayor's Office is more powerful than any other major city in the country)? When you phrase it that way, you might find quite a few rich people or corporations that have the combo of vanity and political desires to set forth that money. You have to look at the bigger picture (much like the massive money that donors send in to fund a Presidential Library). Having lived in Cook County for the majority of my life, $70-100 million amortized over a 20-30 year period (some or all of which might even be tax deductible if structured properly!) really isn't as much as you'd think if what you end up getting is a direct line to the Mayor's office for all of your other business with the city.
Chicago politics is a completely different animal than maybe any place other than New Orleans (who have their own unique style of patronage and corruption). In other cities, the City Council might matter. There could actually be the notion of separation of powers in a place like Hartford or even New York City. In Chicago, that doesn't exist. What the Mayor wants is what the Mayor gets. Period. The Mayor doesn't set forth plans unless they're effectively done deals, and even when they aren't done deals, they might push them through, anyway. (See how former Mayor Daley literally bulldozed Meigs Field in the middle of the night. Speaking of which, Mayor Daley, who gave Rahm his first big political break and even guys as high up as Obama have kissed his ring to start their political careers in the past, is an alum and very large donor to DePaul. What might look like a weird expensive plan to a lot of people across the country is hardly a weird plan to those that know how Chicago politics works and the power players involved.)
