This paper explores the conception, rise, and initial implementation of a legal strategy which sought to fashion civil liability into a tool for reforming the Chicago Police Department (CPD) from the mid 1950s to 1967. Operating under a certain notion of the legal services market, a group of lawyers, working in close concert with the Illinois Division of the American Civil Liberties Union (ACLU), theorized that with the correct imposition of civil liability on police misconduct and brutality, they could weaponize civil suits into a means of forcing the CPD to crack down on abusive and harmful police behavior. Drawing from contemporary thought on how civil liability could shape municipal conduct, they reasoned that this imposition, brought about by plaintiffs sue the City of Chicago directly and expanding the conduct officers could be sued for, could be used to harness the legal services market to cause the number of successful civil suits to become commensurate with the prevalence of abusive police practices. Amidst a culture of impunity and widespread police misconduct within the CPD, they thought the total cost of the resulting civil suits would compel the City to enact reforms to combat such practices and the culture of impunity within the Chicago Police Department. This paper examines the attempt to carry out this legal strategy in the federal civil court system from the early 1950s to the end of Superintendent O.W. Wilson’s tenure in 1967, with a specific focus on police torture and abusive detention practices. I argue that while this may have been a novel strategy, it was ultimately unsuccessful in changing broader departmental policy and priorities. Altogether this is the story of a failed attempt to weaponize civil lawsuits to curb police misconduct and abuse. A close examination of this legal strategy and the assumptions underlying it offers insight into the utility of civil liability to rectify and prevent civil rights abuses by the police.