The authors examine both main effects and cross-level effects of prior criminal justice contact on delinquency and violence. Using multilevel longitudinal data from the Project on Human Development on Chicago Neighborhoods (1994-2001), they addresses a lack of clarity on the effect of police contact on delinquency and violence. The authors found that police contacts (three types) were associated with increases in delinquency and violence. These effects remained robust after controlling for individual-level covariates such as low self-control. Importantly, the effect of jail contact on the number of delinquent acts a youth engages in was stronger in neighborhoods with high levels of legal cynicism. Paradoxically, however, youths with prior police contacts were more delinquent when they lived in neighborhoods that had higher levels of satisfaction with police. Our study provides a more nuanced understanding of the correlation between police contact and future offending and offers insights into how neighborhood characteristics may worsen the effect of police contact, as well as the importance of dissecting types of contact with the justice system. The study offers policy implications for law enforcement.