Conover opens Chapter 5 by describing the eeriness of the Sing Sing grounds, where “thousands upon thousands of lashings” (171) were meted out and hundreds of prisoners were executed by electric chair. Conover describes Sing Sing as a one-hundred-and-seventy-year-old “architectural hodgepodge” (172), where elements of older structures are scattered amongst the prison’s newer buildings.

In 1825, a group of inmates and their keepers travel by boat from the state prison at Auburn, under the supervision of Elam Lynds, a former Army captain. The United States is still devising the methods by which to enforce law and order; corporal punishments, such as hanging and flogging, are characteristic of the time period, but the nature of punishment in the Western world is undergoing a shift. Conover cites Michel Foucault’s observation that punishment has transitioned from torture and public spectacle towards more psychologically-oriented methods.

The Quakers are the first to establish the concept of the American penitentiary—penitence through isolation—and Philadelphia’s Walnut Street Jail serves as the first model. The penitentiary model leads to the creation of a separate holding units for the worst offenders, and in 1821, a new wing is built in New York City’s Auburn Prison that is comprised entirely of solitary cells.