The recently-announced Our Roots Chicago plan from Mayor Lori Lightfoot in Chicago, intended to plant an additional 75 thousand trees in ‘vulnerable’ neighborhoods, was met with surprise controversy when several community organizations protested what they deemed to be the potential for environmental gentrification. Troubling the notion of trees as ‘ahistorical’ or ‘apolitical,’ this paper examines how Chicago residents, in pointing to the ways in which the planting of new trees may not be truly sustainable for their communities, reveal deeper connections between the processes of sustainable development and regimes of racial hierarchy in America’s cities. Expanding on Brandi Summers’ work on “Black aesthetic emplacement,” this paper examines how debates around sustainability become the place of contestation over the modern city, wherein urban policymakers turn to a 'green aesthetic,' concealing larger histories of environmental injustice, attaching symbols of sustainability to spatialized forms, and greening the image of the neighborhood - making it more appealing to private investment - rather than greening the neighborhood itself.