This reminds me of a great thread I read here a *long* time ago, which I can no longer find, despite multiple searches. A poster here is some kind of expert on urban planning and design, and went into detail about why Love Park was changed from a dynamic and interesting plaza that allowed people to congregate for multiple purposes into a boring, pancake flat eyesore. The thrust being that yes, the design is intentional, because cities and the people who police them now see large, unorganized gatherings as a thing that should be interrupted and arrested where possible, and a flat plaza with few openings serves much better for their current intended use, which is "official" events like charity runs and festivals, where someone leases out the park and charges admission. As an added benefit, the authorities can now see everything going on in the park, so no one can get away with something nefarious like drinking in public.
I did a shitty job explaining it, but if someone can dig up that thread, I would appreciate it and I think it would be relevant to the conversation.