Flight to Freedom

When creating the penitentiary system in the 1790s and early 1800s, American reform thinkers intended to make a space separated from society so punishment would no longer be a public spectacle, and so offenders would have an opportunity to reflect and gain skills to rejoin society.[i] If the penitentiary was supposed to be a place for such soul-searching and self-improvement, then what reason would prisoners have to attempt escape? Escape was a risky endeavour, but when the penitentiary failed to be a pillar of reform, it became a valid option for gaining one’s freedom.

Punishments of the Past

The penitentiary system was intended to replace horrific public punishments, and the notorious brutality of the jails of the past.[ii] However, the punishments that were used as replacements were not inherently more humane. Public punishments, such as branding, carting, and being placed in the stocks, were physical pains that would not last forever.[3] A public execution would, of course, destroy a life entirely, but even this extreme public punishment had another side for the person being punished-the chance of a legacy. Public execution drew many people from all different social classes and encouraged watching the execution to be a normal outing.

Death became a spectacle for the observing public and therefore not a deterrent to crime. Instead, criminals who were being hanged were observed with curiosity, especially about how they would handle the moment of their execution. When offenders were brave in the face of the scaffold, taking their punishment without repenting or possibly even mentioning their crimes, this was remembered more than their crimes because this was what the public witnessed.[iv] Criminals did not have a chance to escape these public punishments since they were not lengthy sentences, but brief, brutal, punishments that would soon be over.

Failures of the Penitentiary


Figure 1


Unlike public punishment, in the penitentiary the punishment was the time away from society. In the “separate system” that the penitentiary was based on, prisoners often spent entire days alone in their cells, making it impossible for them to escape even their own minds. Although the time spent alone was not directly responsible for any marks on the body, it had the potential to cause lifelong mental problems. Prisoners of war who were kept in solitary confinement discussed how their memory, concentration, and emotional stability were all affected. One even said that he started bashing his head into the wall one day, having lost control.[v] Scientists studying the effects of solitary confinement note how the human brain recognizes we are social beings, and are meant to be constantly calculating social moves. When a person is left in isolation, in most cases, mental health will deteriorate.[vi] Although the prisoners were not technically all in solitary confinement, they were all kept in isolation for long periods of time, especially over weekends when they did not have work, so the desire to escape was partially their desperate need for human interaction.

Physical Punishment

Although solitude is a trademark of the penitentiary, meant to allow for time to think and reform, physical punishments did not disappear. Use of the shower-baths (shown in Figure 2), whippings, and beatings by keepers were not uncommon in Sing Sing. In 1864 at Sing Sing there were 243 recorded punishments, from shower-bathing to being chained up in a dark cell.[vii] There were quite possibly other punishments that went without being recorded, and since they were within the penitentiary, they went without public notice.


Figure 2

Unlike the days of public punishment, the physical punishments that took place within the penitentiary were in addition to the original sentence of imprisonment. Though the physical pain might only last a little while, it might happen many times during the years a prisoner was locked away, adding to the prisoner’s determination to be free again.

Those Who Did Not Escape


Knowing that the penitentiaries were not in fact the pillars of reform that they were intended to be, one might wonder why many more prisoners did not attempt escape. Even among those sentenced to death or sentenced for life, and therefore with nothing to lose, there were prisoners who did not leap at the opportunity to escape.[viii] According to a former prisoner, escape might not have appeared to be a particularly difficult task. In fact, he says ,“Sing Sing is perhaps the most insecure prison..,” citing the location beside an open river, the lack of significant walls, the railroad passing through, and the lackadaisical attitude of many of the keepers.[ix] The wardens of the prison were aware of some of these problems, asking for funding for a wall in their annual reports. The request continued to be made from 1851 to 1852, and it is clear that no such protective wall was built.[x] The true barrier to escape, the prisoner wrote, was the practically inevitable recapture. Of about 50 escapes made in the last quarter of the nineteenth century, only two prisoners were not returned.[xi]

Some of the escaped prisoners lived for years as free men before being recognized and arrested again; most were recaptured within hours of their escape, and either way, they ended up back where they started.[xii] Newspaper accounts often reported on the escapes after the recapture had already occurred. A typical article from an 1859 edition of the New York Times describes the escape of a Sing Sing prisoner, but ends by saying that he has been recaptured, all of it having happened within one news cycle.[xiii]

Public help, the armed keepers, and the difficulty of swimming across the Hudson River, caused most escapes to end this way. Even years later, the prisons were committed to getting back their escapees. One prisoner, for example, had fled Sing Sing in 1876 and gone to England where he ended up being arrested, but was allowed his freedom so long as he never returned to England. He made his way back to the United States, was arrested for forgery, and served a seven year sentence in Jefferson City. At the end of this sentence, he had been “free” from Sing Sing for 15 years, but as he left the penitentiary, he was met by a New York State Detective and was brought back to complete his original sentence.[xiv]

Punishment Upon Return

Along with the pain and disappointment of recapture, prisoners would be punished upon their return. In newspaper accounts, such as the previously mentioned one in which the prisoner had already been recaptured, the prisoner was put into a darkened cell, and left in solitude. This part of the punishment was published, but the prisoner might be subject to a beating as well.[xv] Another article from 1876 describes a recaptured escapee being attached to a ball and chain for punishment.[xvi] For a prisoner who was already disliked  by keepers or who was violent toward them during his escape, a harsh punishment was a certainty.[xvii]


Figure 3. An artistic example of a cell where an inmate might be left with little to no natural light.

Lost Commutation

There were also certain rules in place regarding the sentences of the returned escapee. Prisoners serving a sentence of less than four years who attempted escape lost any chance at minimizing their sentence with good behavior. Prisoners with sentences greater than four years lost half of their possible commutation, or good behavior time, upon their first attempt at escape, then lost the benefits of good behavior entirely if they made another attempt.[xviii] Some did not get the chance to try again, as was the case for Joseph Hopkins who was shot by a keeper in his escape attempt in 1874. He did not survive.[xix]

No Escaping Stigma

For those who gained freedom at the end of a sentence, their time in the penitentiary stayed with them in public life. In Sing Sing’s annual reports, from the 1850s through the 1870s, there were listings not only of the numbers of newcomers, but also of numbers of criminals being recommitted for their second or third stay. For example, out of 687 new prisoners at Sing Sing between 1861 and 1862, 232 were being recommitted for the second time, 34 for the third time, seven for the fourth, two for the fifth, and one for the sixth.[xx] If a person completed a full sentence without ever attempting to gain freedom, this obviously did not mean that they were out of the system.

Even prisoners who did not turn to a life of crime after their release might find life outside of the prison to be unbearable because they could not rejoin society. John Luckey, chaplain at Sing Sing from 1839 to 1851, wrote in his memoir about a man who had been wrongfully imprisoned, but after his release begged to be retaken. He wrote to Luckey about his struggles, beginning with, “Dear Sir, I have some case to regret that I so soon got out of prison.” Even though he had been wrongfully imprisoned, no one would employ him. He had tried to find his family, but discovered that his immigrant wife and children had returned to England since they did not have their breadwinner, or any friends in the United States.[xxi] Sing Sing had not prepared the prisoner to rejoin society, and society was unwilling to welcome prisoners back as reformed citizens.[xxii]

Escape was an option that, if accomplished, would allow one to abandon the stigma of being a prisoner, so that they might be able to start again. Penitentiaries hid prisoners from society so people could not glorify or even think about them like they had in the days of public punishment. Escape was one of the only ways to make one’s story known to the public. Escapees were listed by name in the paper, and typically the press would recount how they escaped as well. Frank Reilly, for example, who had escaped several times by 1884, was listed in the paper as “An Expert Jailbreaker,” a glorifying title that makes him sound clever and makes Sing Sing sound insecure.

Reilly was a lifelong criminal and frequent prisoner, and therefore not someone who the public would have seen much, nor should have admired, but the New York Times published a lengthy biography about him after one of his escapes; he had become a well-known figure.[xxiii] The press touted escapees as “daring” and “bold,” their crimes seemingly forgotten.[xxiv] In this way, escape could allow a prisoner to gain a reputation for brains instead of sin.

Taking Agency

With such depressing odds, according to one former prisoner who published a book about his time in Sing Sing in 1904 under the moniker “Number 1500,” most of the other prisoners felt that those who attempted escape were fools. Still, whenever they heard the bells alerting the town of an escape, the cell walls became alive with chatter, and when the prisoners discovered who had gotten out, they erupted into cheers, full of hope.[xxv] Many men who Number 1500 interacted with spent every week hoping for a pardon to release them.[xxvi] He also noted how many of the prisoners awaiting death did not seem to really believe that they were going to die, perhaps because they could not bare to think that way.[27]


Figure 4. An inmate puts on the stripes that mark him as a criminal.

Despite the slim chance of obtaining a pardon, avoiding a death sentence, or maneuvering a successful escape, the prisoners held onto hope that it might happen. Cheering for someone else showed their desire for prisoners other than themselves to be free, or just to take advantage of some brief moments of freedom that would show the penitentiary that they still had some agency within their own lives. In spite of the punishments, recaptures, and loss of good behavior, the prisoners would continue to try, gaining notoriety and the chance of freedom on their own terms. Although escape was an impractical decision, the proof of agency and the hope that it gave the prisoners allowed even unsuccessful escape attempts to have some reward.

-Maggie Douglass



[i] Mark E. Kann, Punishment, Prisons, and Patriarchy: Liberty and Power in the Early Republic, (New York: NYU Press, 2005), Proquest Ebrary Version, 118.

[ii] Ibid, 130.

[iii] Ibid, 119.

[iv] Ibid., 118.

[v] Elizabeth Bennion, “Banning the Bing: Why Extreme Solitary Confinement Is Cruel and Far Too Usual Punishment,” Indiana Law Journal 90, no. 2: 741-786 (2015), EBSCOhost, accessed October 10, 2016.

[vi] Ibid, 755.

[vii]  Gaylord J.  Clarke., James K. Bates, and D. P. Forrest. Annual Report of the Inspectors of State Prisoners. Vol. 18th. 1864/1865. (Albany: New York State, 1865), accessed October 16, 2016.

[viii] Number 1500, Life in Sing Sing (Indianapolis: The Bobbs-Merrill Company, 1904), accessed October 15, 2016, 115.

[ix] Ibid, 183.

[x] Darius Clarke, William P. Angel, and Henry Storms, Annual Report of the Inspectors of State Prisoners, Vol. 5, 1852, (Albany: New York State, 1853), accessed October 16, 2016.

[xi] Number 1500, 187.

[xii] Number 1500, 201.

[xiii] “Troubles at Sing Sing State Prison,” New York Times (1857-1922), August 30, 1859, ProQuest, accessed October 16, 2016.

[xiv] Number 1500, 203.

[xv] “Troubles at Sing Sing State Prison.” New York Times (1857-1922), August 30, 1859.

[xvi] “ATTEMPTED ESCAPE FROM SING SING.” New York Times (1857-1922), September 29, 1876, ProQuest, accessed October 20, 2016.

[xvii] Number 1500 189.

[xviii] Thomas Byrnes, Professional Criminals of America, (New York: Cassell & Company, 1886), accessed October 14, 2016, 393.

[xix] “ATTEMPTED ESCAPE FROM SING SING.” New York Times (1857-1922), September 29, 1876, ProQuest, accessed October 20, 2016.

[xx] James K. Bates, D.P. Forrest, and Abraham B. Tappen, Annual Report of the Inspectors of State Prisoners, Vol. 15th, 1861/1862 (Albany: New York State), 1863, accessed October 15, 2016.

[xxi] John Luckey, Life in Sing Sing State Prison as Seen in a Twelve Years’ Chaplaincy, (U.S.: N. Tibbals, 1860), accessed October 12, 2016, 249.

[xxii] Tanzina Vega, “Out of Prison and out of Work: Jobs out of Reach for Former Inmates,” CNNMoney, October 30, 2015, accessed October 28, 2016.

Even hundreds of years later 76% of former prisoners say that finding a job is nearly impossible due to stigma, according to a 2015 CNN article.

[xxiii] “AN EXPERT JAIL-BREAKER,” New York Times (1857-1922), January 6, 1884, ProQuest, accessed October 20, 2016.

[xxiv]“OTHER DARING ESCAPES,” New York Times (1857-1922), May 11, 1893, ProQuest, accessed October 21, 2016.

[xxv] Number 1500, 204.

[xxvi] Ibid., 158.

[xxvii] Ibid., 102.


Figure 1: Interior of  a Convict’s Cell. 1858. Harper’s Weekly. Correction History. Accessed October 17, 2016.

Figure 2: Shower Bath. 1858. Harper’s Weekly. Correction History. Accessed October 17, 2016.

Figure 3: Exterior of a Convict’s Cell. 1858. Harper’s Weekly. Correction History. Accessed October 17, 2016.

Figure 4: Inmate’s First Day at Sing Sing. 1860. Sing Sing Prison Punishment. Accessed: October 17, 2016.