@CateCAParent - maybe I’m reading the list of top endowments wrong? To me, the main driver for wealth seems to be: prestige. The top endowment list for the private schools reads more or less like a ranking for prestige. Some of the schools have middling sports programs (Harvard, Columbia, etc.), some have negligible sports programs (UChicago, MIT, Wash U), and a few have notable sports programs (Stanford, Duke, Notre Dame).
But, aside from Notre Dame, all the wealthy privates have one thing in common: they are the country’s most eminent schools.
To me, it seems like Chicago’s options to grow its wealth are:
1.) Increase its eminence and its optics about eminence (e.g., move up in rankings)
2.) Invest billions to create a winning football or basketball team (e.g., Notre Dame or Duke)
Investing to create a middling sports program would be a curious decision indeed. Creating a big-time sports program seems too costly, and a risky use of resources.