For as clueless or as uncaring as Marty might seem about how his behavior appears to others, he does recognize the importance of optics when it comes to other people—hence his telling Barack to find someone other than Will to be the face of this push, and hence his hiring Barack, a Black man, in the first place. And yet, Will still understands Chicago differently than Marty does, despite his eccentricities. As a part of the community, he understands better that outdoor meetings like these will be far more successful than Marty’s preferred indoor meetings.