Seeking Freedom: Stories of Escape Attempts at Sing Sing

By the mid-19th century, punishment in the United States had been removed from public view, and moved into penitentiaries. For prisoners in Sing Sing, which opened in 1828, prisoners were housed in a cell block that was 476 feet long and 44 feet wide with four tiers. The building sat on 130 acres of land, 33 miles from New York City. The penitentiary was located within the village of Ossining, along the Hudson River.[i]


Figure 1

Although it did not always have a wall, being surrounded by the villagers and the river still made Sing Sing a difficult place to leave. Escape, therefore, was not an easy task, requiring either immense planning, or tremendous amounts of courage during an opportune moment. Still, escape attempts continued, each year from the prison’s 1828 opening through the nineteenth century, with sometimes as many as five escapes being successful, in a single year as in the year 1859.[ii]  Before recounting some of the specific ingenious tactics used by escapees, we must examine some of the context around escape in general.


Figure 2. The wall that was later built at Sing Sing.

Crimes of Escapees

In Figure 3 there are examples of some of the crimes committed by 20 prisoners who attempted to escape Sing Sing in the second half of the 19th century.[iii] Although those listed below all attempted escape, the types of escapes that prisoners were capable of might have differed depending on their background.


Figure 3

The 4 convicted of murder were in prison for life, or were awaiting death sentences. In 1840s New York, the median sentence for assaults was two to five years, two and a half to three years for forgeries, and 49 months to five years for burglaries.[iv]

Escapes were almost always being attempted, as demonstrated below in Figure 4, showing that the problem was extremely prevalent.


Figure 4

[v]            These numbers do not show us how many of these escapees might have been recaptured, but what we can see is how many attempts continued to be made, each one having a story. These escapes might involve spontaneity, intense planning, inside help, or violence, but they all shared the same motive: freedom. The escapes were attempted in a variety of ways, each of which calls attention to flaws of the penitentiary and the way that they might be exploited by prisoners.

Violent Escapes

The population of a penitentiary included some criminals incarcerated for violent offenses. One prisoner who was at Sing Sing for six years during the 1890s ended up publishing a memoir about his experience, including information about some of the escapes that occurred during his time, and also mentioning some that he had heard about while incarcerated. The former prisoner, using “Number 1500” to preserve his anonymity, described one 1893 attempt involving two violent prisoners, Pallister and Roehl.


Figure 5

The men were both awaiting the electric chair, and seemingly decided that escape was the only option. When a keeper came to Roehl’s cell with coffee, Roehl pushed him up to the wall of the adjoining cell where his partner, Pallister, helped to secure and incapacitate the keeper. Roehl stole the keys and pistol from the keeper, then freed Pallister.[vi] Although Roehl and Pallister had masterminded the plan, the men stopped and asked another death row inmate to join them, but he declined. The duo continued on alone, climbing up and cutting a hole in the roof. The prisoners then waited for the guard who they knew would be doing rounds soon, quieted him with the threat of the pistol, and locked him in a vacant cell.

The patience of waiting for the guard that they knew was coming was one of the most important parts of their plan, the next round by guards would not be made until the morning, buying them hours before anyone would be on their trail. The search for the escapees went on for two weeks, which would have given them a great deal of clearance. However, at the end of the two weeks, the men were found dead.

Most of the prison officials agreed that they ended up fighting and killing each other. This theory only gains credibility by the fact that both men were awaiting the electric chair for something that was said to be “weird and dark,” implying that they may have been violent.[vii] The New York Times covered the initial news, and then released a second article, also written before the men were found in 1893. The second article included theories about how they might have gotten away successfully on a boat.[viii] Since the escapees were known to be violent, the Times likely published more articles about this escape since it would be a topic that aroused public worry and interest as it made Sing Sing guards seem like they lacked control.
More Violent Escapes

Other prisoners involved in violent, multi-person escape attempts were able to work together without such fatal ends. The 1875 escape that would go on to become Sing Sing’s most famous included five prisoners, and the cooperation of so many prisoners is part of what caused the story to gain notoriety. Two of the prisoners were working on the railroad which cut through the prison yard. The prisoners were armed with a pistol and rushed onto the engine of a train that was passing through. They were joined by three more inmates on the train. The prisoners used their numbers to their advantage, separating to fight off and force both the fireman and engineer off the train. Meanwhile, another of the five prisoners was able to release the engine from the rest of the train, and they raced away on the engine.

The engineer had smartly turned off the water pipe, so the engine was quite literally going to run out of steam and without control the men were heading toward the river. However, the prisoners had were past the prison yard already and jumped off of the engine, escaping on foot into the woods.[ix] Four of them ended up recaptured and returned to Sing Sing to complete their lengthy sentences. One, however managed to gain passage to England where he opened a pub and became a respected member of his community.[x] The story itself traveled far as well since it involved so many inmates at one time. It was written about from New York to Australia, calling global attention to the possibility of criminals conspiring and escaping their imprisonment, an idea that would have both scared and intrigued the public.

Another violent escape in which people working at the prison became victims involved a prisoner of spectacular strength who was at Sing Sing in the mid-1880s. Selected for his strength, the prisoner joined a few other men and keepers to load some heavy stones in the quarry which was on the banks of the Hudson River. Like the men who escaped on the train, this prisoner had the advantage of already being outside, but he still had keepers near him. The prisoner paused, acting as if he simply needed to tie his shoe, allowing the keepers to get just a few feet ahead of him. Then, while the keepers were vulnerable since he was behind them, the prisoner lunged at them, taking one by the throat and knocking the other one unconscious. The other prisoners, unsurprisingly, did nothing to stop the man and he escaped. He was not recaptured, but the injured keepers felt that this was a good riddance, not wanting another violent interaction with the prisoner.[xi]

Deceptive Escapes

Other escapes relied on no violence at all, but were still quite daring and called attention to the need for attentive keepers. Prisoner James Curry, for example, who Number 1500 said had been imprisoned a few years prior to him, was employed in one of the shops manufacturing saddlery at the prison. He stole a great bundle of white hairs from the mane and tail of a horse, out of which he he fashioned a beard. With the false beard fixed upon his face and a coat and cap on, the prisoner must have looked convincingly like the contractor who employed him.

He rode out of the prison with two horses, as the contractor usually did, and the guards were convinced that it was indeed the contractor. The man’s absence was not even noticed until the keepers realized the horses were gone, which gave Curry a good start, but he was recaptured still. Upon his return to the prison Curry was harshly beaten and kept in a darkened cell for 10 days. The darkened cell would have been a typical punishment for the escape attempt, while the beating may not have been reported.[xii]

Use of Dummies

There were quite a few escape attempts in the early twentieth century in which prisoners left dummy versions of themselves so that they would not be missed when the keepers were doing rounds. Two examples, one from 1919 and one from 1916 are shown below. The prisoner represented in Figure 6 was returned within six weeks. The other, shown in Figure 7, who put his skills as an artist to work, is not noted as having been returned. Both likely hid their supplies under their beds and used materials they could easily access, like clothing, bits of bread dough, and hair.[xiii] After another escape using a dummy in 1926, the penitentiary finally decided to have the prisoners stand outside for the headcounts, showing how the prison often had to react to the actions of the prisoners.[xiv]


Figure 7


Figure 6

Utilizing Corruption

Taking advantage of unethical keepers was another possible way to slip through the cracks. According to Number 1500 many keepers may have been complicit in providing prisoners with certain supplies or aiding in their escape attempts with some promise of reward, but it was a great risk for the keepers too. For example, two men wishing to escape their lifetime of imprisonment at Sing Sing paid off a keeper named John Outhouse in 1874, and he let them out during his rounds and allowed them to get away. The keeper’s involvement went for some time undetected, but when he attempted to use some of the money that one of the men had paid him, it was found that the money was counterfeit. Outhouse would have been prosecuted for attempting to pass counterfeit money, but he admitted how he got it, and was instead prosecuted and convicted for assisting in the escape. The keeper became the imprisoned and ended up falling into a life of crime even after his release, eventually spending most of his days at Sing Sing for different crimes.[xv]

Exploiting Prison Knowledge

Beyond exploiting corrupt keepers, there were other parts of the system that prisoners could use to their advantage. Labor and employment at the prison was a major part of how prisoners were supposed to be reformed, but it also meant that they might have knowledge of certain processes, such as the way that products left the prison. A large and strong prisoner named Frank Koehler, for example, began his time at Sing Sing in 1873 on a sour note. Koehler was not familiar with one of the keeper’s customs of poking passing prisoners with his club, so when he was poked, he immediately responded with an attack on the keeper. Koehler was harshly punished for the act, and though the keepers mostly feared him thereafter, he presumably could not stand being treated as a subordinate.

Only two months into his sentence Koehler got a fellow prisoner to nail him into a barrel as if he was one of the products that the prison would be shipping out. Koehler and his accomplice knew about the way the products looked when being shipped from the prison. Using this knowledge, they were able to make the barrel look just like the others and it was put on a boat with the prison exports. Koehler emerged from the barrel once the boat was on the Hudson River. Though his dress gave him away as a prisoner, he still managed to escape into the water, living freely until he was arrested years later in Pennsylvania.[xvi]

John Luckey, Sing Sing chaplain from 1839 to 1851, wrote a great deal about his experiences at the prison and his interactions with prisoners during his 12 years of employment. He noted two escape attempts made by water, one of which involved wood shavings from one of the manufacturing shops that employed prisoners. Luckey wrote about the incident only briefly, but it involved a prisoner who escaped by attaching two wooden casks from one of the prison shops, then covering the casks and himself in wood shavings from one of the manufacturing buildings on the grounds. The prisoner knew that shavings were always tossed in the water, so guards would not be alarmed, especially if the prisoner’s absence was not yet known. When, at some point, prisoners were being counted, the keepers realized that one was missing; only the casks could be found, the prisoner was already free.[xvii]

Damage of Prison Property for Escape

Another escape described by Number 1500 was achieved through the damaging of prison property. Charles Williamson, a smart man who had been involved in various money scams and forgeries throughout his life, had been sentenced to 15 years in Sing Sing. Charles was employed at the prison, working at the prison bakery. Since the bakery needed to provide food by each meal time, those workers often were not brought back to their cells until later. One night in 1877, it was discovered that the bakery was on fire. The primary goal was to extinguish the flames, so no one was looking into the possibility that a prisoner had started the fire as a distraction. In all the excitement, Williamson escaped and no one noticed until he was well down the Hudson where he paid off a ship captain and eventually gained passage to England. Once again, the idea of buying time to get away proved to be an important part of planning an escape, probably meaning the difference between Williamson’s freedom and his recapture, which did not come until significantly later in England.[xviii]


Figure 8. An 1880 fire started by an inmate in a Sing Sing factory.

Outside Help

Chaplain John Luckey noted how much planning one prisoner put into his 1853 escape by water, probably formulating his idea immediately upon arrival. The particular prisoner had previously completed a three year sentence, but was recommitted for life after being found guilty of burglary. He escaped a mere three months into this second sentence.

Upon arriving at Sing Sing, the prisoner had obtained a great deal of ‘gutta percha,’ a latex material formed from a certain tree sap.[xix] As prisoner accounts like that of Number 1500 have established, procuring materials was a possibility if one established a relationship with a keeper, although Luckey does not specify that this is how the gutta percha was obtained. The prisoner created tubing from the material, which he attached to hollow, decoy ducks. This whole apparatus was attached to a water tight jacket and hood, so that his face and body would be protected from water, and the tubes connected for breathing, like a snorkel.[xx]

There were still two hours until the end of the work day, giving the prisoner some time to sneak down to the river before he would be expected back in his cell and he began to swim across. The decoy ducks floated above the water, allowing the prisoner to breathe without attracting suspicion. One of the ducks became detached, but he still managed to complete the swim and reach the shore where some correspondent was waiting with plain clothes and some money.[xxi]

Since the striped garb of a prisoner was designed to make them stand out and was immediately recognizable, acquiring a change of clothes was a key part of any well planned escape. After only a few weeks of freedom the prisoner returned to New York where he had not yet been forgotten, and he was recaptured. However, the change of clothes and supplies used for his swim across the river had helped him to evade immediate recapture, showing how contact with the outside world could be critical.[xxii]

Spontaneous Escape

Not every escape attempt came with pre-planning. Some escaped by taking advantage of incidents when the prison or keepers were insecure. In the case of one prisoner, Yorkey, an attempt at escape was a case of this luck. Yorkey, who was imprisoned at the same time as Number 1500 in the 1890s, had been employed as a mason when he was a free man, so at the prison he had been called upon to repair a section of the wall in the yard. Yorkey was already outside, but there were still several guards and keepers watching over the grounds, and one specifically supervising his work on the wall. There was also a post that had been abandoned by a prison officer, but the uniform that the officer had worn was left behind.

A bell rang to signal the end of the work, and the supervising guard immediately went towards the gate that was being opened. There were other guards, but when outside they would sometimes smoke or rest in chairs, not paying close attention to any particular prisoner. All of these serendipitous factors had to be considered at a rapid pace by Yorkey. Although he had not been planning to escape, when the prisoner found himself already outside, beside a hole in the wall, and with clothing so easy to obtain, the attempt seemed worth making. Yorkey pulled on the uniform and ran away, stopping to hide under a bridge when the alarm alerted everyone to his escape.[xxiii]

Yorkey was actually recaptured by the warden who participated in the hunt, presumably because they knew almost immediately that Yorkey had left and were able to start the search before he could get far from Sing Sing. Yorkey was not too harshly punished as the warden was pleased to have captured the prisoner himself, and in fact Yorkey was allowed to resume work.

For some prisoners, especially those who had been known for their good behavior and who took their recapture well, punishment may not follow, especially since the loss of good behavior time they had earned might seem like punishment enough for the most well behaved prisoner. For example, a man named Danny asked for his old job and cell back when recaptured and his request was granted because he had been well-behaved while a prisoner and often had visits from his upper class family, especially his sisters.[xxiv]

For Danny or Yorkey, escape and recapture did not end up causing much harm, but even in this rare case, freedom was not permanently attained, remaining a desirable, yet nearly impossible, dream. Still, the stories noted here show the many different ways escape might be attempted, and despite the difficulty and unlikeliness of permanent freedom, escapes called attention to, and took advantage of, the many flaws in the penitentiary system in a way that came directly from the prisoners themselves.

-Maggie Douglass

[i] John Luckey, Life in Sing Sing State Prison as Seen in a Twelve Years’ Chaplaincy, (U.S.: N. Tibbals, 1860), accessed October 12, 2016, 13.

[ii]Isaac Comstock, John Gedney, David Spencer, et al. Annual Report of the Inspectors of State Prisons, Years 1848-1853 and 1857-1865 (Albany: New York State, 1848-1853, and 1857-1865), accessed October 16, 2016.

[iii] Number 1500, Life in Sing Sing (Indianapolis: The Bobbs-Merrill Company, 1904), accessed October 15, 2016, 194.

[iv] William Francis Kuntz, Criminal Sentencing in Three Nineteenth-Century Cities, (New York & London: Garland Publishing, Inc., 1988), 157.

[v] Annual Report of the Inspectors of State Prisons, Years 1848-1853 and 1857-1865.

It is important to note that the last 6 columns come from a time when annual reports collected information on parts of two years at a time, and the years 1854 through 1856 are not included.

[vi] Number 1500, Life in Sing Sing, 114.

[vii] Ibid., 115-117.

[viii]“MURDERERS STILL AT LARGE,” New York Times (1857-1922), April 23, 1893, ProQuest, accessed October 16, 2016.

[ix]“Convicts Capture a Railway Engine and Ride Off,” Australian Town and Country Journal, July 31, 1875, accessed September, 30 2016, 26.

[x] Number 1500, Life in Sing Sing 190.

[xi] Ibid., 196-197.

[xii] Ibid., 189-191.

[xiii] Guy Cheli, Sing Sing Prison, (Charleston, SC: Arcadia Pub., 2003), 23.

[xiv] Ibid., 80.

[xv] Number 1500, Life in Sing Sing, 191-194.

[xvi] Ibid., 194-195.

[xvii] Luckey, Life in Sing Sing State Prison as Seen in a Twelve Years’ Chaplaincy, 242.

[xviii] Number 1500, Life in Sing Sing, 202.

[xix] Luckey, Life in Sing Sing State Prison as Seen in a Twelve Years’ Chaplaincy, 244.

[xx] Number 1500, Life in Sing Sing, 242.

[xxi] Ibid., 243.

[xxii] Lewis Edward Lawes, Life and Death in Sing Sing, (Garden City, NY: Doubleday, 1928), 63.

[xxiii] Number 1500, Life in Sing Sing, 191.

[xxiv] Ibid., 193.


Figure 1: Sing Sing Prison Aerial, 1920. Wikimedia Commons, Bain News Service. 5 Jan. 2013. Accessed, October 3, 2016.

Figure 2: Levine, David. Modern Day View of the Prison Wall. Sing Sing Prison, Ossining, NY: A History of Hudson Valley’s Jail Up the River. HV Mag. Sept. 2011. Accessed Octber 3, 2016.

Figure 3: Graph made by author.

Figure 4: Graph made by author.

Figure 5: Tiers of Cells at Sing Sing. Jimmy “the Shiv” Death House Barber of Sing Sing. Accessed October 3, 2016.

Figure 6: Cheli, Guy. Sing Sing Prison. Charleston, SC: Arcadia Pub., 2003.

Figure 7: Cheli, Guy. Sing Sing Prison. Charleston, SC: Arcadia Pub., 2003.

Figure 8: Cheli, Guy. Sing Sing Prison. Charleston, SC: Arcadia Pub., 2003.