Ok, I’ll bite: his goal is for every stakeholder to feel listened to, for their lives to get better, for no one to have an undue advantage, and for people to generally have what they need and want to the extent possible.
"But what's really happening there is that there are in fact very well-defined Latino neighborhoods in Chicago, and the earmuffs capture a bunch of them neatly: Pilsen, Little Village, Cicero, Belmont-Cragin. If you know Chicago, you know these places, and you also know what the boundary between, say, Belmont-Cragin and North Austin is like; however artificial it looks on a map, it is a real border. That these communities are where they are is also not purely happenstance: a lot of very unfortunate social engineering took place in the early-mid-20th century to put those neighborhoods (and all the other neighborhoods) where they are now."
Assuming his goal is to protect the unique culture of that neighborhood, two options are:
1. the neighborhood already has its unique culture protected because the people in that neighborhood help elect the city government
2. the unique culture of the neighborhood is not sufficiently protected by the city government, therefore the neighborhood should incorporate and so become its own independent city
Again, whatever Thomas's goal is, I'd suggest that he achieve his goal directly, rather than trying to achieve the result as the accidental side effect of other architectural decisions. Gerrymandering is a very weak way of trying to defend the culture of a neighborhood. If his goal is to protect the culture of the neighborhood, then he should think of an architecture that would do so directly.
What’s the next step, then?