Could it be that those wealthier peer schools have more wealth than they actually need or can use effectively - at least at the undergraduate level? If Chicago is doing just fine by its own lights with the endowment it now has, that outcome speaks for itself. If with a yet greater endowment it could satisfy every conceivable student need - as the ivies are said to do - I would consider that a negative outcome for this school with its history and values. Excessive wealth concentrated in a few schools is part of the problem, not the solution.