This brief examines the fractured relationship between residents in high-crime Chicago neighborhoods and the police that serve those communities. Based on surveys of people living in and police officers serving in four Chicago police districts on the city’s south and west sides collected as part of the evaluation of the Chicago Violence Reduction Strategy, these data demonstrate ambivalence between the police and residents. Community members do not generally perceive the police as acting in a procedurally fair manner and do not support their work; this perception is particularly high among individuals with recent arrest histories in co-offending networks. Police officers do not believe the community trusts them, and officers express little confidence or trust in those living in the districts they police. However, residents are generally willing to cooperate with the police on crime control efforts.