This chapter analyzes two countries where criminal economies have thrived in marginalized urban communities, yet only Brazil experiences localized criminal wars while Argentina faces limited violence. The chapter explains how the Brazilian military dictatorship developed a counterinsurgent state with an extensive intelligence and repressive apparatus that allowed its specialists in violence’s involvement in illicit economies. The first democratic government failed to hold authoritarian specialists in violence accountable, and validated a military-era amnesty law, enabling the survival of the counterinsurgent state. Authoritarian security forces adapted counterinsurgency practices to launch wars on crime, sold protection to gangs, or controlled illicit markets, turning Brazil into one of the world’s most violent democracies. The chapter then discusses the development of Argentina’s counterinsurgent state. It analyzes the role of the security apparatus in developing a clandestine carceral system to perpetrate gross human right violations and the participation of authoritarian specialists in violence in illicit markets in dictatorship. After transitioning to democracy, Argentina’s first administration initiated a robust truth commission and the historic trial of the military juntas, unlocking Latin America’s most powerful accountability shock. Multiple truth and justice “boosters” contributed to dismantle the counterinsurgent state, to deflate criminal markets, and to put the country on a path of relative peaceful development.