Resistance by Prisoners at Sing Sing Penitentiary

At Sing Sing Penitentiary during the early 1800s, prisoners often attempted to usurp the regime put in place by the prison. Prisoners would resist the guards in various ways, a result of the terrible conditions they lived in as well as their horrible treatment. This resulted in riots, escapes, fighting with prison officials, arson and more. Much of this action took place against guards, a reaction to how prisoners were abused by the guards as well as how negatively they reacted to the labor they were forced to perform. While some instances of the prisoner rebellion were successful, many were not and oftentimes the inmates involved would face even greater punishment as a result. For many, resistance was a means of achieving prison reform, with prisoners acting out in order to protest the actions of the guards and the prison itself.

Reasons for Resistance


Figure 1

There were many motivations for prisoner resistance at Sing Sing. The most prominent and perhaps the most obvious purpose was a desire to provide retribution to the guards for the punishment inflicted upon the inmates. Prisoners were subject to horrendous treatment and beatings from the guards, and they were prevented from fighting back. Regardless of whether they hoped to physically defend themselves or even if they just wanted to plead with the guards or the prison as a whole for help, the prisoners went unheard. This invisibility of the prisoners is described in Levi S. Burr’s “A Voice from Sing-Sing,” in which he Burr discusses how punishment was inflicted on a near constant basis. According to Burr, prisoners were told by guards that the only way they could avoid punishment was to “get in line, keep silent, and work harder,” despite that never stopping the guards from inflicting beatings.[i] Burr’s goal in writing his pamphlet was for the New York State Legislature to understand and correct the terrible conditions the prisoners faced at the hands of the guards, but his pleas for help went unanswered.[ii] The Assembly of New York did not care that prisoners were being mistreated, as it was assumed that they deserved it. Burr’s pamphlet is essentially a form of resistance in itself, fighting back against the prison system from the outside.

Another major reason for resistance was the inmate’s desire to escape from the prison. In regards to breakouts and escapes from the prison, most of the inmates who left did so for one of two main reasons. First, prisoners attempted to escape in order to return to their outside lives, including their families and work life. Escape was used as a way to return to a life of happiness and normalcy, desiring a stability that prison could not provide.[iii] Secondly, prisoners would attempt to escape in order to leave behind the life of the prisoner at Sing Sing, meaning escaping from the guards, labor, and conditions of the prison. For this, the prisoners cared less about going home to their families than they did leaving behind the prison.[iv] For cases of this kind, prisoners were more likely to fight their way out of the prison, and this led to many of the brawls and riots that Sing Sing eventually became famous for.[v]

Forms of Resistance

On the prison’s grounds, three of the most common forms of resistance were rioting, arson, and fighting with guards. In the middle of the 19th Century at Sing Sing, each of these types of rebellion was used repeatedly, with a wide array of results. For some, rebellion was a success and led to actual change in the prison system. For others, it only resulted in greater punishment, or possibly even death.



Figure 2

Riots at Sing Sing were not the most common occurrences but nevertheless happened, with instances being covered by the New York Times across the 1850s and 1880s. In one such instance in 1855, two guards were shot by an inmate during a riot, the result of one of the guards losing his weapon in the struggle. Much of the focus of the Times article is on the death of these guards, looking primarily at the lives and deaths of these two men without ever providing a look at what occurred during the riots. However, brief mention is made of a different inmate being shot and killed by a guard, dead in his cell and showing “signs of a struggle.” [vi] This disparity in how the stories of the guards and the prisoners are told is apparent in many of the articles in the New York Times, with a greater emphasis often placed on those who have not been convicted of crimes. While this difference is not entirely unexpected, it does provide a look at how the mass media covered these riots.

Also interesting about this article and others is how it shows the inmates clearly having broken one of the cardinal rules of Sing Sing, which was keeping the prisoners from talking to one another. In a perfect world the prisoners would be unable to communicate and therefore share information. However, in the case of this riot, the leader of the riot had told the inmates about the impending fight and used a code phrase to incite the battle.[vii] A similar instance regarding communication used in rioting occurred in 1859 when inmates had secretly decided upon a time to act and an unknown signal to begin fighting. [viii] Another riot in 1874 contained over sixty people in its ranks, with all of the members knowing the exact time and place to strike, knowing the plan shared amongst one another. [ix]

Riots overall were uncommon because they required large amounts of organization and planning, something prevented due to this emphasis on maintaining silence. While it is not surprising that these riots did involve some talking between inmates, it does show how the perfect silence expected across Sing Sing was never completely maintained. The strict enforcement of silence made collusion between the prisoners much more difficult, but it did not make it impossible. But because guards could never fully prevent inmates from talking, riots were still able to occur.[x]


Another common form of rebellion at Sing Sing was the setting of fires within the prison, often to protest around labor at the prison. Arson was a much more difficult crime to pin on a single individual because of how the fires would not require a prisoner to be at the location at the time of ignition. There were two major fires at between the 1850s and 1880s that caused large amounts of damage to the infrastructure of the prison.

The first occurred in 1855 and involved a fire starting in a clothing factory on-site at Sing Sing. The damages from the flame ended up costing the prison over $80,000 dollars with the clothing factory needing to be rebuilt from the ground up. During the fire, a group of prisoners escaped from Sing Sing, with the fire likely lit as cover. An article about this fire in the New York Times that year also mentioned that this was the fifth in a string of similar fires at the prison, with each resulting in the escape of a number of inmates.[xi]


Figure 3

In 1879 another fire was lit with similar motivations, with the hope being that the guards would be distracted by the fire while inmates escaped from the prison. The prisoners had hoped to burglarize Sing Sing prior to their escape, stealing as much as they could from the prison before fleeing. However, the prisoners were recaptured before escaping, returning what they had stolen. One of the prisoners was found to be in possession of equipment needed to escape from the. Instead of setting the fire in a clothing facility, this fire was started in the center of the prison with the hope of causing as much damage as possible to the prison.[xii]

In the case of each of these fires, prisoners hoped to use the chaos they created as a way to escape. However, in setting the first fire at the clothing facility, the belief was that prisoners were attempting to protest the labor at the prison, burning to the ground a place where the inmates had worked.[xiii] By setting fires that damaged the prison, the inmates were able to hurt Sing Sing in a way that attacking the guards could not. By forcing Sing Sing to repair the damage done to the prison, changes could be made to how the penitentiary operated overall, possibly improving conditions of life for all of the prisoners.

Fighting With Guards

Oftentimes resistance would take the form of a single person fighting back against a guard, although this was typically more dangerous for the inmate himself. The prisoner attacking would usually be quickly outnumbered by guards at the prison, in some instances resulting in the death of the inmate.[xiv] These forms of resistance were much more based in emotional temperament and how a prisoner felt in a time, meaning it was less likely for the inmates to plan attacks of this nature ahead of time.[xv] In one example of this, an inmate notable for his ability to escape from jails found himself fighting with a guard. While the prisoner had the upper hand, the guard managed to use the escapist’s own hubris against him and took him down physically as well.[xvi]


Figure 4

Much of the emotional motivation for inmates was based in the cult of masculinity and manhood that existed in the prisons. Manhood is often defined as combining a sense of independence with familial leadership and responsibilities. Because both of these things were immediately removed when one becomes a prisoner, prisoners often acted out in different ways, usually related to showing strength and masculinity over another. In these cases, these emotional outbursts were often in the form of fighting against guards, invoking force over another man and controlling a situation. This was the inmate’s way of enforcing their own masculinity and becoming the “man” the prison prevented them from being.[xvii]

Inmates fighting with guards occurred often enough, although it was usually only a single prisoner. Small groups would occasionally fight a guard together, but this was a much rarer event. Regardless, fighting with guards would often involve terrible punishment for the prisoner, including forced solitary confinement or punishment bordering on torture to the inmates.[xviii] Punishments were generally worse for prisoners who attacked guards with intent to escape, the prisoners often put into solitary confinement for days on end or beaten viciously.[xix] Fighting with guards was often a temporary form of resistance, with the prisoners seeking emotional catharsis instead of reform.


Resistance against Sing Sing Penitentiary and its guards was a main form of rebellion against the prison system. The ability for prisoners to leave their forced positions and either fight through escape or physically by attacking, rioting and so on gave escaping prisoners a greater level of control over their situations, even if only temporarily.

-Liam Haber

[i] Burr, Levi S. A Voice from Sing-Sing: Giving a General Description of the State Prison. Albany, NY. 1833. p. 31

[ii] New York (State) Legislature. Assembly. Documents of the Assembly of the State of New York. Volume 57, Issues 3-4. Albany, 1834. p. 2

[iii] Number 1500. Life in Sing Sing. Indianapolis, 1904. p. 190

[iv] Graber, Jennifer. “Engaging the Trope of Redemptive Suffering: Inmate Voices in the Antebellum Prison Debates.” Pennsylvania History: A Journal of Mid-Atlantic Studies 79.2 (2012): 209-33. Accessed November 12, 2016. p. 227

[v] “A Convict’s Fight for Liberty.” New York Times. February 05, 1880.

[vi] “Rebellion at the Sing Sing Prison.” New York Daily Times (1851-1857): November 29 1855.

[vii] Ibid.

[viii] “Attempted Revolt at Sing Sing State Prison.” New York Times. August 06, 1859.

[ix] McLennan, Rebecca M. The crisis of imprisonment: protest, politics, and the making of the American penal state, 1776-1941. Cambridge, 2008. p. 98

[x] Graber, p. 226

[xi] “Destructive Fire at the Sing Sing Prison.” New York Daily Times. December 07, 1855.

[xii] “Large Fire in Sing Sing.” New York Times. August 14 1879.

[xiii] New York Daily Times, Dec 1855

[xiv] Gilfoyle, Timothy J. A Pickpocket’s Tale: The Underworld of Nineteenth-century New York. New York: W.W. Norton, 2006.. p. 162

[xv] McLennen, p. 148

[xvi] “An Expert Jail-Breaker.” New York Times. January 06, 1884.

[xvii] Kann, Mark E. “Penitence for the Privileged: Manhood, Race and Penitentiaries in Early America” Black and Pink. p. 21-31

[xviii] Gilfoyle, p. 168

[xix] Number 1500, 192


Figure 1: Newgate Prison Burned by the Rioters. 1780.

Figure 2: Inside Newgate. 1845. George Cruickshank.

Figure 3: The Mob destroying & Setting Fire to the Kings Bench Prison & House of Correction in St Georges Fields. c.1780-85. British Museum, Crace XXXIV.40

Figure 4: Wirz Stamping on a Prisoner. 1865. Harper’s Weekly.