This episode explores the notorious and haunting history of Eastern State Penitentiary, detailing its origins, the failed Pennsylvania system of solitary confinement, the harsh conditions faced by inmates, and notable figures like Charles Dickens who criticized its practices along with some infamous inmates such as Al Capone. The conversation also covers infamous escape attempts and the evolution of security measures within the prison. The conversation then explores the elaborate tunnel escape plan of 1945, the chaos of the 1961 riot, and the eventual closure of the prison. It also highlights the eerie experiences reported by visitors and the unique Halloween events that celebrate the penitentiary's haunted legacy.