In 2023, Chicago implemented a novel form of police oversight: Police District Councils (PDCs). In each of Chicago’s 22 police districts, elected three-member boards serve as the “eyes and ears” of the community, reporting issues to local police commanders and the citywide Community Commission for Public Safety and Accountability (CCPSA), which, in theory, has the power to effectuate systemic change within the Chicago Police Department (CPD). This report analyzes the effectiveness of PDCs within the broader history of police oversight in Chicago, comparing them to a similar model in Los Angeles. Utilizing three interviews with Police District Councilors, observations of council meetings in Districts 2 and 14, analysis of news articles, and review of local ordinances, this paper finds that PDCs lack structural power due to political compromises made in City Hall. This has severely limited their impact, leading to internal conflicts, low community engagement, and resistance from city officials, weakening their legitimacy as an oversight mechanism. This report provides insights for cities seeking to implement democratic policing reforms while illustrating the challenges of balancing community-driven oversight with entrenched institutional power.