Discipline and Punishment in Sing Sing Prison from 1828 to 1870

Sing Sing prison, from its very foundation 1828, became a system of punishment within itself. Convicts found themselves at the mercy of their keepers, under the tyrannical rule of the prison warden, known in the 19th century as the Agent. Sing Sing’s first warden, Elam Lynds, set a standard for harsh punishment based on the doctrine that without strict discipline, such a group of criminals could not be kept under control. He sought to break the spirit of his prisoners, and establish prisons as a place of terror to potential criminals.[i]

Lynds’s vision prevailed, and Sing Sing became an institution of cruel discipline administered through many different means.

Convicts were punished often and harshly. Largely thanks to the influence of Elam Lynds, flogging became the first line of punishment in the first three decades at Sing Sing. Guards were encouraged to hit prisoners with anything they had on hand, including brooms, the heavy canes many keepers carried around, and their fists and feet.[ii] Most whippings, however, were conducted in a predetermined place called the Flogging Post. Inmates were stripped and tied to two iron rings fastened to the wall, while the keeper they had offended took his pick of whips hanging on the adjacent wall. According to an 1841 legislative report, “More than a hundred blows were struck daily…The whipping post was never dry.”[iii]


Figure 1: The Cat-o’-nine-tails. The ends of this vicious whip were hardened, waxed, and knotted – some even went as far as to put bits of metal in the knots.

The most vicious of these whips was favored by Lynds: the cat-o’-nine tails (see figure 1). The cat-o’-nine-tails was made of six to nine leather strips of hard chord, sometimes knotted and sometimes containing metal shards to maximize pain. The cat-o’-nine-tails had horrific potential in experienced hands; as stated by a warden in 1846, “an inexperienced keeper of but ordinary muscular power, when using the Sing Sing cat would scarcely heighten the color of the skin by a dozen blows, while a vigorous practical keeper, by adopting a peculiar swing in raising the cat and a drawing motion in striking, can cut the skin at nearly every blow.”[iv] The cat-o’-nine-tails was used ruthlessly: guards partnered with each other, trading off to ensure that as they tired the intensity of the blows wouldn’t diminish. Although this method meant that the fiftieth lash did as much damage as the first, the response of the victim steadily diminished, for his nerve endings would be dulled or destroyed. If a prisoner became listless, guards dripped salt water into their wounds to check they were still alive. For those who could still respond with gasps of pain, the crack of the cat continued.[v]


Figure 2: A prisoner secured to the whipping post.

The cat-o’-nine-tails had devastating effects on the convicts. A report from 1839 recounts the testimonies of two assistant keepers who witnessed extreme cases. John Mattucks, assistant keeper from 1832 to 1836 claimed he witnessed three hundred strokes of the cat administered all at once upon a convict for raising a weapon to a keeper. Following this punishment, the convict could not work, and was therefore further punished with a low diet and confinement to his room. Mattucks reported that this punishment seemed to have left him deranged.  Daniel Odell, assistant keeper from 1832-1839, told the story of a convict who, upon being recaptured after a failed escape, was given one hundred lashes with a cat of six strands and subsequently drowned himself two days later.[vi] Not all convicts even survived to suffer the mental aftermath of the cat. One such case is that of Theodore Whitting, a convict who some guards suspected to be mentally unstable, but regardless was flogged for every transgression. After a particularly lengthy flogging, guards administered salt-water sponges to the open wounds and got no response from Whitting; he was dead.[vii]

The death of Whitting was one of the cases that led to public outcry against the practices at Sing Sing. Many protested the brutality of whipping and legislature responded by abolishing the cat-o’-nine-tails in 1848, disproving Lynds’s assertion that it was impossible to govern such a prison without such a ‘cat-ocracy.’[viii]

According to a 1846-1847 legislative report, in those final years of its use floggings consisted 341 of the 551 punishments administered.[ix]

However, other than flogging, and especially after the cat-o’-nine tails was eliminated, there were many other means were used to enforce discipline. An example of these punishments, as well as what they were inflicted for, can be seen in this sample from the annual Sing Sing state Agent’s report:


Figure 3


Figure 5


Figure 5

The most infamous form of punishment was the Shower Bath, also known as the Cold Water cure. A device resembling medieval stocks secured the convict’s hands and feet, leaving him trapped directly underneath a barrel suspended about four feet above. The barrel would be completely or partially filled, depending largely on the temperament of the keeper administering the shower, with cold water that was especially icy in the winter months. The water would then be released upon the convict with great impact. In later years, the water would be released less forcefully, but a wooden collar would be fixed around the convict’s neck to collect the water and create the sensation of drowning. This punishment was particularly popular because it did not leave any visible markings on those who had suffered it. Indeed, The warden of Sing Sing in 1853 reported that “There are none of these punishments calculated to produce physical injuries, and a careful examination of the effects of the shower-bath enables me to say that it is not only a prompt and salutary corrective for the turbulent, incorrigible and unyielding, but that its physical effects are invariably beneficial.”[x] In reality, however, the damage it caused could be physically and psychologically devastating. The account of Auburn prison physician Blanchard Fosgate bears witness to several convicts who lost their sanity or died due to the cold water cure. Despite this, it was among the predominant forms of punishment in Sing Sing until it was finally abolished following violent prison riots in 1869.[xi]

The coolers were another form of both psychological and physical torture. They were 18 completely dark, isolated cells that reportedly reeked like a sewer and were shared by convicts and cockroaches. Convicts thrown into these cells were confined to starvation rations of bread and water, and those who survived came out deathly ill or insane.[xii] An average of 100 men per year were kept in these cells for varying amounts of time, and the practice continued until 1914, when authorities finally labeled the practice as ‘unhealthy.’[xii]


Figure 8

From existing records, there were two different kinds of punishments involving pulleys that were used at Sing Sing. One form, pictured in Figure 8, suspended the prisoners’ hands above his head and also lifted one leg, leaving almost all of his weight on one foot, a position that became extremely painful after being held for some time.[xiv]

The other kind of punishment that used the pulleys in the punishment room was much faster acting; a method known as ‘tricing’ by the thumbs. Victims would be strung up by the thumbs, having their entire weight suspended in a moment of shocking pain. Nobody could endure this punishment longer than a matter of seconds, a fact that was attested to by Colonel J.L. Broome upon his investigation of Sing Sing in 1879, where he subjected himself to the ‘tricing’ punishment and could withstand if for only 40 seconds.[xv]

The prison records also report ‘bucking’ as a form of punishment at Sing Sing. Bucking was a form of punishment that saw its heyday in the military discipline of the Civil War. A person would be forced to sit in a crouched position with a rod inserted between his legs and elbows, his wrists and ankles bound for complete lack of mobility. Insubordinates would often be left thus for over six hours, and when unbound would be left unable to walk and often sobbing.[xvi] Other records show that bucking involved hanging the victim upside-down by the rod inserted under his knees, occasionally raised into a sitting position and then releases to swing back and forth.[xvii]


Figure 9

Another such form of punishment through sustained discomfort was the yoke, a bar of flat metal weighing 30-40 pounds that would be placed on the neck and shoulders of the convict, whose hands would be attached to the bar behind his neck. The persistent presence of such a weight against the top vertebrae caused increasing pain as time slowly ticked by. According to what keeper John Ashton told prison inspectors, “I think that not one man in a thousand could stand up under the 40 pound yoke for four hours.” Indeed, the yoke could be debilitating even after lifted from its victims’ shoulders; one account from an 1851 legislative committee told of an inmate who endured four hours of the yoke as punishment for poor work and could not leave his cell for two weeks due to his pain.[xviii]

The Ball and Chain was especially popular for use on prisoners who had attempted to escape. A heavy iron ball would be affixed with a chain to an iron girdle clamped around the prisoner’s waist, adding strain to his every move. Guards could add further weight when they say fit.[ixx]


Figure 10


Figure 11

The crown, or the cage, was a device made of metal that would be affixed around the prisoner’s neck. Some accounts claim that the purpose of the crown was primarily for the humiliation of the wearer, while others report that the nature of the spike and the collar caused pain upon the slightest movement.[xx] This device is also likely a form punishment through sleep deprivation, as the pain caused by movement would render it impossible for the wearer to sleep. The crown would be worn day and night for the duration of the punishment.[xxi]

Other punishments were conducted through shaming the convicts. One of the most common forms of punishment documented in the Sing Sing annual reports is shearing, or shaving the convicts’ head. This was done with to humiliate and demark the offending prisoner, further evidencing the complete control that guards had over the body of the convict.

While women prisoners did not share in all the same punishments as the men, they too were harshly dealt with. Women who broke the rules would be gagged and have their hair cut off, and could then be put on a starvation diet. Those who most incurred the wrath of the guards might have been suspended by the wrists with their toes barely touching the ground, or have been flogged with the cat-o’-nine tails.[xxii]

Discipline in Sing Sing prison was irregular throughout the 19th century.   Different forms of punishment gained and lost popularity due to changes in administration and legislation. For example, in the earliest years of Sing Sing, flogging was the primary form of punishment, until it was outlawed in 1848. The Shower bath then enjoyed its heyday until 1869, when it was in turn supplanted by the paddle.[xxiii] A sample of the annual records from this mid-19th century time period gives a picture of this fluxuation. To view this visualization of discipline types and trends from the years 1848, click here.

– Briana Boland

[i] Lewis, David W. From Newgate to Dannemora, The Rise of the Penitentiary in New York, 1796-1848, (New York: Cornell, 1965), 87.

[ii] Lewis, Newgate to Dannemora, 150.

[iii] Conover, Ted, Newjack, Guarding Sing Sing (Toronto: Random House, 2000) 177-178, quote from 178.

[iv] Lewis, Newgate to Dannemora, 98.

[v] Brian, Denis The Inside Story of a Notorious Prison, Sing Sing (New York: Prometheus, 2005) 21-22.

[vi] Conover, Newjack, 179.

[vii] Brian, Sing Sing 28-29.

[viii] Conover, Newjack, 181.

[ix] Legislative Report, Documents of the Assembly of the State of New York, Volume 6, No 160

[x] New York (State) Inspectors of State Prisons. Annual Report of The Inspector of State Prison, 1853 (Albany: 1853) pg 22

[xi] Conover, Newjack, 182-183.

[xii] Brian, Sing Sing 22.

[xiii] Cheli, Guy Images of America: Sing Sing Prison (Chicago: Arcadia, 2003) 24-25.


[xv] McLennan, Rebecca M. The Crisis of Imprisonment: Protest, Politics, and the Making of the American Penal State, 1776 – 1941 (Cambridge University Press, 2008), 129

[xvi]Katcher, Philip The Civil War Source Book (Facts on File, 1992)

[xvii] Department of Correction, Sing Sing Prison, Ossining, NY: Its History, Purpose, Makeup and Program (New York State, 1958), 6

[xviii] Conover, Newjack, 181

[ixx] Brian, Sing Sing, 22-23

[xx] Brian, Sing Sing 22

[xxi] Department of Correction, Sing Sing Prison, Ossining, NY: Its History, Purpose, Makeup and Program, 7

[xxii] Brian, Sing Sing 30

[xxiii] Department of Correction, Sing Sing Prison, Ossining, NY: Its History, Purpose, Makeup and Program, 5


Figure 1:  https://en.wiktionary.org/wiki/cat-o’-nine-tails

Figure 2: Cheli, Guy Images of America: Sing Sing Prison (Chicago: Arcadia, 2003)

Figure 3: New York (State) Inspectors of State Prisons. Annual Report of The Inspector of State Prison, 1858/59 (Albany: 1860) pg 32

Figure 4: Brian, Denis The Inside Story of a Notorious Prison, Sing Sing (New York: Prometheus, 2005)

Figure 5: Art and Picture Collection, The New York Public Library. “Punishment Of Convicts — Torture And [Dea]Th By The Shower-Bath At Sing Sin[G].” New York Public Library Digital Collections. http://digitalcollections.nypl.org/items/510d47e1-1dde-a3d9-e040-e00a18064a99

Figure 6 and Figure 7: Cheli, Guy Images of America: Sing Sing Prison (Chicago: Arcadia, 2003)

Figure 8: http://www.correctionhistory.org/html/chronicl/fatal1858showerbath/auburnprisonshowerbathdeath.htm

Figure 9: http://hubpages.com/education/American-Civil-War-Life-Union-Infantryman-Life-In-Camp-Hygiene-Sanitation-and-Illness-and-Crime-and-Punishment

Figure 10: Brian, Denis The Inside Story of a Notorious Prison, Sing Sing (New York: Prometheus, 2005)

Figure 11: http://www.correctionhistory.org/html/chronicl/fatal1858showerbath/auburnprisonshowerbathdeath.htm