There is limited empirical research related to lawsuits involving the police due in part to limited accessibility to relevant data sources. This study aims to examine the relationship between citizen, situational, and lawsuit factors and police misconduct litigation in the city of Chicago. Data were collected from two separate databases: The Chicago Reporter and The Invisible Institute. The analyses in this study demonstrate that there is a relationship between lawsuit payout amounts, lawsuit misconduct type and various situational factors. Policy implications are discussed.