My impression is the police screwed up the initial contact. Too many nervous Nellies are being hired too quickly with too little training and too little seasoning ... all in the name of "putting more cops on the street." This is what you get.
In their defense, I'm guessing legal gun carriers are far from common in that neighborhood, and Chicago in general. When they see someone obviously packing, their default assumption is 'bad guy'. I was impressed how chill the first cop who is talking to him is. He seemed to have the situation under control.