My Dad tells me that more than who is on the Board, the big difference is how the board gets elected or confirmed at Chicago compared to the other schools like his alma mater Harvard or Yale or Princeton. I think for the Chicago board, alums get no say in the matter. Other Board members decide who else gets on the board.
So younger and more progressive alums cannot stage a coup and get a bunch of board members elected that could fundamentally alter the priorities of the administration within five years. My guess is that if there were a lot of alum appointed trustees on Chicago’s board, the postures of the college towards free speech and other controversial issues for example may have been very different.
There is no way for younger Chicago alums who might want to change directions or the school’s priorities to get any say on the Chicago board and this may be the reason, Chicago is in some ways so different from other schools right now.
Not sure how this may affect Chicago in the long run, but right now, as an outsider looking in, I feel it may be the reason the administration is a little more moderate and little less likely to pander to current students and their activism. President Zimmer can just “No” to the students or not worry about making a huge “faux pas” like Lawrence Summers made at Harvard by making some controversial statement and risk losing his job because a young alum dominated board loses confidence in him.