More than 600,000 prisoners are released from incarceration each year in the United States, and most end up returning to metropolitan areas, concentrated in resource-deprived neighborhoods. To the extent that convicted criminals are distrustful of the criminal justice system, the funneling of massive numbers of former prisoners back into select neighborhoods likely facilitates the reproduction of legal cynicism in those areas. Accordingly, this study tests the effect of prisoner reentry on the culture of neighborhoods, particularly with regard to legal cynicism. Using two-waves of data on the geographic distribution of returning prisoners in Chicago from the Illinois Department of Corrections combined with data on neighborhood characteristics from the US Census, the Chicago Police Department, the Project on Human Development in Chicago Neighborhoods, and the Chicago Community Adult Health Study, I conduct a cross-lagged analysis of the effect of the concentration of returning prisoners on legal cynicism as well as the effect of legal cynicism on the geographic distribution of returning prisoners. Findings reveal that a dense concentration of returning prisoners in a neighborhood facilitates the reproduction of cynical views of the law in the neighborhood. The substantial growth in the number of releases from prison and the stark concentration of the formerly incarcerated in select neighborhoods has detrimental consequences for the culture of receiving neighborhoods.