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The U.S. Interstate System is the most robust public works project in American history. While highways enabled cross-country travel and longer commutes, ample evidence suggests that their construction disproportionately displaced communities of color. However, research has not yet explored how the wide-scale demolition of residences and local social institutions that facilitate collective efficacy (e.g., churches, schools, barber shops) may have shaped criminal justice system demand and structural disadvantage within affected communities. This study addresses this gap by employing marginal structural modeling to explore the consequences of highway construction and building demolition across census tracts in 19 large American cities (≥ 500,000 residents). I first evaluate the factors shaping highway placement and the impacts of highway construction on the destruction of local social institutions (LSIs), residential dwellings, and population shifts. Finally, I analyze how the demolition of LSIs and residences mediates the relationship between highway construction and criminal justice system demand (e.g., crime, calls for service, traffic enforcement). The findings I present have implications for the long-term consequences of inequitable urban planning on criminological outcomes and structural disparities.