I'm sure, knowing Trump's character, he's neither forgotten nor forgiven this and is determined to get some sort of payback.
^The fascist knows his fascists. This has very little to do with any meaningful concern for the people of Chicago, and everything to do with the fact that the President is a senile old man who spends most of his free time being Mad Online. The right-wing posters here pretending to care about gun violence are doing a hilariously poor job at excusing a move that would be entirely aimed at political intimidation.
Anyway, any "occupation" would be an utter disaster. The people being put under martial law in this scenario do not trust the person giving the order, and Chicago has already demonstrated that it has a more aggressive and organized left-wing movement than any other city. People are proud of what happened last time Trump tried to come here. Not endorsing the idea of mass resistance against the national guard, but would be less surprised if it happened in Chicago than anywhere else.
This is the reason why we need to occupy it. The aggressors must be punished.