Isaac and Jack join Jarrod Shanahan, an activist, educator, and the author of Captives: How Rikers Island Took New York City Hostage, for a wide-ranging conversation. We cover the last 70 years of New York City's political history from the lens of the city's jails. We discuss the various actors fighting for control in the city: the politicians and bureaucrats responsible for the administration of jails, the repressive jailers and their corrupt labor union, the revolutionary social movements struggling for liberation inside and outside prison, the non-profits brought in to plug the budget holes and keep the peace, and the capitalists profiting from it all. After examining the shifts in political hegemony within New York City - from liberal "penal welfarism" to the neoliberal "war on crime" to a resurgent, reactionary "revanchism" - we reflect on how this history informs our current organizing in the abolitionist and public sector union movements. We end with a discussion on the 2024 elections and Jarrod's most recent article for Hard Crackers, "Iowa Bluffs," focused on his experiences at a recent Trump rally in Dubuque, Iowa.