Donald Trump’s 2016 presidential campaign rhetoric about violence in Chicago spatialized a narrative that branded the city as the poster child of urban disarray. His bombast lacked any contextual understanding of the issue and offered no productive pathways for collective solutions. Alternatively, I argue in this paper that a rising collection of Chicago hip hop artists were producing musical discourses in 2016 that not only challenged Trump’s negative rants, but also spatialized a multilayered narrative of the intersections between hip hop and activism in the city. Through textual analysis of three tracks from three breakout artists in 2016, my goal is to show how hip hop enables audiences to imagine Chicago’s 1) structural resistance to violence in the city’s communities of color, 2) a sense of place and belonging among the city’s youth, and 3) a loving and unapologetic “black liberation” lens to social movements in the city.