The 2020 Black Lives Matter protests placed significant pressure on local governments to fund nonenforcement alternatives to policing. One prominent example of such alternatives is the Cure Violence model. Cure Violence (formerly CeaseFire), a Chicago-based violence prevention organization, practices a model of violence prevention known as “violence interruption,” in which outreach workers, many of whom used to be gang-affiliated, leverage their local knowledge of the communities where they work to prevent gang violence. Despite this model’s growing popularity around the country and the world, however, the program is no longer in existence in Illinois, in part due to its having lost government funding on three occasions. These funding cuts were surprising given the organization’s popularity among legislators at the time, its continued success nationwide, and the state’s shifting role as a funder, rather than an executor, of public policy. Drawing from interview, archival, and newspaper data, I attempt to answer the question, “Why has Cure Violence struggled to retain long-term government funding from the city of Chicago and the state of Illinois?” I identify three challenges to long-term state funding faced by Cure Violence: (1) a tense relationship with police, (2) a fraught relationship with certain legislators, and (3) a loss of public trust resulting from several high-profile scandals the group was involved in. Although these findings are specific to Cure Violence’s Chicago operations and are therefore not generalizable to other cities, they raise areas for further exploration about the nature of state and nonprofit relationships that extend to other contexts.