“The Prison Has Failed”: The New York State Prison, In the City of New York, 1797–1828 Jonathan Nash (bio) During the evening of April 4, 1803, convicts attempted to escape from the New York State Prison, in the City of New York (commonly called Newgate). This was not the first time that convicts resisted confinement at New York’s first state prison. During its first six years of operation, prisoners frequently rebelled, set fires, and tried to escape.1 Although the historical record for this incident is fragmented—newspaper articles and a report to the New York State Legislature—it provides an opportunity to analyze prisoners’ responses to incarceration. Some inmates, such as Daniel McDonald, a convicted horse thief sentenced to seven years of hard labor, the alleged “ringleader” of the uprising, persistently resisted incarceration.2 On the other hand, Isaac Lytle and other inmates refused to join the uprising. Lytle may have hoped that his good behavior would lead to an early release. Other prisoners, such as Comfort Carpenter, who was convicted of forgery and sentenced to life imprisonment at hard labor, perhaps aligned with keepers (guards) during the rebellion in hope of receiving a pardon that might reunite them with family and friends.3 McDonald and his cohorts may have spent days, weeks, or even months planning their escape. Between five and six in the evening, McDonald and a handful of prisoners set fire to one of the apartments—a room that confined at least eight prisoners. When keepers arrived to extinguish the fire, the men escaped from the apartment and rushed into the prison’s interior [End Page 71] courtyard. A keeper reported that McDonald claimed that he was “unjustly imprisoned” and therefore “he would escape over the Walls of the prison.”4 In the prison’s courtyard, McDonald and his followers encountered another group of prisoners working as blacksmiths and nailers. These men “refused to join” the uprising. Some inmates went further; they pledged to protect keepers “at the risque [sic] of their own lives.” Rebelling prisoners climbed a scaffold in hope of scaling one of the prison’s exterior walls to regain their liberty. A keeper rang the prison’s bell to alert keepers and residents of the surrounding neighborhood that an uprising was unfolding. Keepers ordered prisoners “to desist.” Rebelling prisoners pelted keepers with “very abusive language” and “brick bats and hammers.” Keepers responded by peppering prisoners with bullets, and in time, regained control of the prison.5 Not all prisoners participated in the rebellion. Isaac Lytle attempted to avoid the melee. Lytle stayed inside his apartment and watched the unrest from a window. According to keeper John Bailey, Lytle “was uniformly a well behaved man, and did not discover the least disposition to join the riot, or to have any kind of concern with the rioters.” Lytle’s attempt to secure his safety by staying inside his apartment failed. When keepers shot at the escaping prisoners, a stray bullet penetrated his skull. Later that evening Lytle died.6 Other prisoners, such as Comfort Carpenter, refused to assist the rebelling convicts. Carpenter was a forty-seven-year-old white-male farmer from Rutland, Massachusetts. When two prisoners invited Carpenter to join the uprising, he declined. The two prisoners “seized” him. Carpenter escaped their hold. He “declared that he would die rather than be concerned in such an attempt to break the prison.” Undeterred, uprising prisoners “armed with knives and hammers, threatened vengeance to all who would not join them.” Carpenter and the convicts who refused to participate also armed themselves with knives and other tools from the prison’s workshops. According to keeper Bailey, prisoners Daniel Callahan, George Thompson, and James Dongherry pledged to protect him during the uprising. [End Page 72] After keepers and a militia company opened fire on prisoners, keeper Thomas Hartley declared: Let me entreat you to desist from further violence; consider the danger you are in; you are sporting away your lives as of no value; see that poor unhappy being, who is now apparently breathing his last, and who was with you a few minutes ago; put a stop to your hazardous attempt now, and it...