In this episode, former DEA Deputy Administrator Jack Riley takes us back to the gritty streets of late-1980s Chicago, where drugs, dirty cops, and the notorious Chicago Outfit ruled the shadows. Riley recounts an explosive investigation that exposed officers like Nick Rosado and Nedrick Miller—sworn to uphold the law, but instead working hand-in-hand with organized crime. With the help of daring undercover cocaine buys, relentless surveillance, and wiretaps, the case blew wide open, leading to the downfall of more than 30 players in the city’s criminal underworld, including corrupt cops, jail officials, judges, and even councilmen.