Through a qualitative analysis of case studies from Boston in the 1970s and 1980s, this article explores how police officers exploited sex workers in pursuit of department goals and personal desires, all while attracting opposition from sex workers and their allies, who likened cops to pimps. Examining police-sex worker interactions documented in the commercial press, alternative media, appellate court rulings, and police documents, this article incorporates the police-as-pimp metaphor to elucidate the nature of police discretion in the context of sex work. When dealing with sex workers, officers proved willing to choose lawlessness if it helped them accomplish other personal and professional goals. Yet this article goes beyond condemning individual police officers as pimp like. Rather, the metaphor applies to entire law enforcement institutions, whose structures and norms facilitated state exploitation of sex workers.