This chapter reconsiders the work of Ludwig Hilberseimer (1885–1967) and his commitments to a socially progressive and environmentally informed modern planning practice through his opposition to the traditional street grid. Through his work as an architect, urban planner, and educator, the German émigré articulated an alternative model of urban order that was highly critical of the traditional street. Over decades of work, Hilberseimer proposed the editing, erasure, and replacement of the nineteenth-century street grid of the American city in favor of a decentralized, distributed tissue of walkable urbanity. Hilberseimer’s skepticism regarding the traditional gridiron street pattern was based on his understanding of the incredible violence that automobility subjected to pedestriansPedestrians in the city. These concerns could not be timelier for those committed to the relations between walkabilityWalkability, automotive violence, and environmental justiceEnvironmental justice. While it has become commonplace to posit various social values accruing to traditional urban typologies, most notably the traditional street, Hilberseimer was committed to urban planningGreen urban planning as a social task and advocated for the protection of pedestriansPedestrians from the dangers of the street. In contrast to traditional street grids, Hilberseimer developed the “settlement unit,” a safe, walkable residential community in which populations were directly connected with playgrounds, public parks, and green spaces while insulated from the violence of automobility.