^ Since 2010, not 2000.
There’s no question that, in the second half of the 20th Century, Chicago’s regular alumni giving seriously lagged that of its academic peers, at least insofar as the College was concerned. There were several overlapping reasons for that.
One of the most important was the size of the College. While most of its peers expanded their undergraduate colleges in the post-war period, and then again when they went co-ed around 1970, Chicago’s College actually shrank quite significantly in the 1960s-1980s, at one point falling below 500 students per class. Various solutions were considered, including moving to the suburbs, merging with Northwestern, and simply closing the College down. When a college isn’t graduating a lot of students, it will tend to have less alumni giving than similar colleges graduating more students.
Second, the College alumni Chicago was creating in that period tended to be ambivalent about the institution. Chicago’s self-image was one of intellectual rigor and asceticism. Students were expected to work hard with little reward, and the University did nothing to foster extracurricular activities. It was no fun – those were the days that gave rise to the “Where Fun Comes To Die” slogan. Alumni tended to be very proud of their education at Chicago, but they often lacked warm memories about that period of their lives and good associations with the University. The Marine Corps basic training facility at Camp Lejeune doesn’t get a lot of grateful alumni donations, either.
Third, Chicago’s single-minded focus on academic ability and academic training meant that, unlike the Ivy League, it was not educating a cohort of future leaders and entrepreneurs who were doers rather than thinkers, nor was it cultivating generations of loyalty in wealthy families. Chicago’s College alumni, compared to Ivy League alumni, were disproportionately academics and government bureaucrats as opposed to corporate executives, entrepreneurs, and politicians. So they were less wealthy as a group.
All of these issues got hashed out in a massive long-range planning report about 15 years ago that encapsulated the thinking of the current generation of Chicago’s leaders, especially Richard Zimmer and John Boyer. It recommended and explained the decisions to expand the College to its current size, to make admissions more holistic, and to invest real money in improving undergraduate quality of life. Those efforts – which began before the report, but accelerated after it – have been sensationally successful for the University in many ways, including, I believe, for its fundraising. (I wish I could find the report somewhere online so I could link it. But I looked and looked, and haven’t found it.)