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This paper explores the history of exclusion and incarceration in NYC, its role in the development of the city, and how this forms the background for understanding NYC’s penal institutions as they exist today and the inequities within the city’s social fabric. One of the themes is that of invisibility. Within the city, there are few signifiers to the locations of early institutions of confinement – a small plaque to Blackwells’ penitentiary exists on Roosevelt Island, and many of the more privileged New Yorkers remain unaware of the location of the notorious Rikers Island jail complex or the city’s other penal institutions. The paper focuses on the voices of those who have been incarcerated in NYC over the years, especially at Rikers Island, and aims to contribute to the wider conversation on the politics of historical memory, and what we choose to memorialize. It starts with the colonial city, drawing from archival research and oral history, and explores the debate introduced by E.H. Carr in What is History? (1961) about the importance of learning from the past, especially in relation to criminal justice reform movements. It builds on the core tenets of critical criminology in its consideration of why and how institutions of incarceration came to be seen as such a “natural” part of society and as an acceptable solution to the social problems that have been confined there.