Convicts at Large: Escapes and the Public

Although the penitentiary system is associated with a separation of prisoners and the public, for the towns where penitentiaries are built they become an integral part of the society. For a small town, having a state penitentiary can actually be desirable since the increased population gives the town increased representation in government. On top of this, there is the possibility of jobs within the penitentiary for citizens of the town. Still, there are certain negative factors since the public is in close proximity with criminals. The risk of having convicts escape is a complicated problem. Escapes are a point of stress, but also created a possible chance of reward for citizens who recaptured the convicts, both of which will be further discussed.


Figure 1. An artist’s depiction of a serene Ossining.

When keepers realized that a prisoner was missing at Sing Sing, an alarm bell and whistle would be sounded to alert the public. One ex-con known as “Number 1500,” wrote a memoir about his time at Sing Sing, including the information he had about escapes from word getting around while he was a prisoner, and from some common knowledge about more famous escapes. The initial way that they found out an escape had happened is also detailed in his book. As he put it, “The alarm whistle and bell gave the news to the villagers and country people.” The siren was a shrill blast that might wake people up at any hour.[i] Since its opening the penitentiary was trying to find fast, far reaching ways to alert the public about trouble, eventually taking to the radio in 1933.[ii] The citizens had become so accustomed to life with a prison in town that the sound of the alarm was unmistakably alerting them that a prisoner had escaped. Sing Sing was embedded into the lives of the people of Ossining. According to Number 1500, once the alarm was heard, the citizens would drop everything and abandon work to begin a manhunt for the escapees.[iii] Of course it makes sense that the public would not want criminals who should still be in prison to be roaming their town. However, convicts who attempted escape would not stay in Ossining; they would want to get far away to avoid being easily recognized. Although this would mean they were not a direct threat to the citizens of Ossining, these citizens had other motivations to return the escapees to the prison.

Rewards and Justice

The typical escape attempt was foiled before the prisoner had made it off of the property, so the keepers stopped the prisoner, not the public. Once a prisoner had made it outside of Sing Sing, the public would be searching as well. If the prisoner was not found within the day, the next newspaper would include an article with the some description of the prisoner and their escape attempt and offering a reward for their recapture. The fifty dollar reward for return was typical in the nineteenth century, as it appeared in the 1893 escape of Charles Smith, for example, who had snuck out during his work in the kitchen.[iv] With many people searching, it might not be likely that you would be the one to take home the reward, but the idea at least made it worthwhile to take time out of one’s work, or other activities, to participate in the search, as people in Ossining would do on the first day when they heard the siren.


Figure 2. A map of the town with the prison in the lower left corner.

Along with rewarding the successful searcher, there was the reminder that the prisoner needed to be returned because their escape attempt was a bad thing, something to be punished. When reporting on the escapes and recaptures, the press often included a follow up on what happened when the prisoner was returned and how they were punished.

One 1859 New York Times article wrote about the escape attempt of a man who had tried to stay outside and escape in the night. The man was captured the same day by keepers, and therefore the public would not have needed to worry about him, but the article ended with, “He was captured and is now in a dark cell, on a diet of bread and water.”[v] A similar article from 1876 told its readers that the convict mentioned in it was punished for his escape attempt by being kept in a dark cell with a ball and chain.[vi] Escape stories might be framed as being bold and clever, with headlines like “Other Daring Escapes: Bold Dashes for Freedom…” from 1893, but by ending articles with mentions of the dark cell or the ball and chain, the press reminded the public that the escapes were acts to be punished, and prisoners needed to be returned so this justice could be served.[vii]


As previously mentioned, convicts did not typically stay in Ossining when they were free, no matter how they gained their freedom, so the Ossining citizens did not necessarily have to think about the idea that there could be a dangerous convict roaming free elsewhere.


Figure 3

Headlines like the 1920 one shown in Figure 3 portray convicts as monsters, wreaking havoc across the nation.[viii]


Figure 4

This similarly sensationalized headline in Figure 4 about the escape of death-row convicts Pallister and Roehl also continues with the fear-mongering, even after the convicts have died.[ix] The press coverage could make it seem like escapes were most definitely going to interfere with the public, and could dramatize the stories so that they felt interesting, and therefore nerve wracking, to every audience, including people in Ossining and in other states.

Constant Exposure

The story of Pallister and Roehl was sensationalized and reported on almost constantly. At first, the idea that two armed death row convicts had escaped was certainly scary for the public, but even after the men’s bodies were found, several more stories followed. The story mentioned above was joined by countless others that detailed and questioned every aspect of the escape, from the gun they had, to whether the keeper who they had beaten was corrupt.[x] Even as late as 1910, 17 years later, articles were written about their escape. The 1910 one refers to them in the subheading simply as “Pallister and Roehl,” still names that they assume the public will know.[xi] The public is never allowed to forget.

Many escapes were written about after the criminals were already back in their cells. One 1869 escape is noted in a New York Times article that detailed the escape itself and attempts at recapture, then in the final sentence informed the reader that the prisoner was actually returned to the prison without even making it half a mile into his escape.[xii] Occasionally, updates were not even connected with a specific escape. An 1893 story let the public know that there were only eight criminals still at large who were known to have escaped Sing Sing, all others having been recaptured, although their recapture may have come years later. This article was released at the time of Pallister and Roehl’s escape, but it did not focus on them, instead just reminding readers of the many escapees who had come before, how constant the problem was, and how important recapture had been.[xiii]

The widespread reporting on prison breaks normalized them as they seemed to always be present in the media and therefore in the world. The way that the articles focused on the specific criminals allowed those criminals to gain notoriety since the public knew their name, their story, and their description. However, this also reminded citizens of the crimes of the prisoner, showing that attempting to escape was a problem of the prisoner, not a problem with the penitentiaries. Meanwhile the sensationalism of the stories themselves kept the public alert to the idea that they needed to return these people to prison for punishment before they damaged society. When escapes were made in Ossining, the people knew it was simply time to catch the prisoner and put them back.

-Maggie Douglass


[i] “ESCAPES SING SING DROPS INTO HUDSON,” New York Times (1857-1922), September 14, 1921, ProQuest, accessed 2 Nov. 2016 .

[ii] “PRISON GETS RADIO ALARM,” New York Times (1923-Current file), July 27, 1933, ProQuest, accessed November 2 2016.

[iii] Number 1500, Life in Sing Sing (Indianapolis: The Bobbs-Merrill Company, 1904), accessed October 15, 2016, 189

[iv] “CONVICT SMITH ESCAPES,” New York Times (1857-1922), January 11, 1886, ProQuest, accessed October 22, 2016.

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

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

[vii] “OTHER DARING ESCAPES,” New York Times (1857-1922), May 11, 1893, ProQuest, accessed November 14, 2016.

[viii] “SING SING FUGITIVES TERRORIZE TOWNS, HOLD UP AUTOISTS,” New York Times (1857-1922), October 18, 1920, ProQuest, accessed October 17, 2016.

[ix] “HOW THE MURDERERS DIED,” New York Times (1857-1922), May 21, 1893, ProQuest, accessed October 20, 2016.

[x] “ROEHL HAD MURPHY’S PISTOL,” New York Times (1857-1922), May 23, 1893, ProQuest, accessed October 20, 2016.

[xi] “THE WAYS IN WHICH MEN ESCAPE FROM SING SING,” New York Times (1857-1922), October 16, 1910, ProQuest, accessed October 20, 2016.

[xii] “Still another Attempt to Escape from Sing Sing,” New York Times (1857-1922), May 29, 1869, ProQuest, accessed October 21, 2016.

[xiii] “OTHER ESCAPES FROM SING SING,” New York Times (1857-1922), April 22, 1893, ProQuest, accessed October 16, 2016.


Figure 1: Havell, Robert. Hudson River North to Croton Point. ca. 1841. The Ossining Historical Society Museum.

Figure 2: Dripps, M. Map of Sing Sing. 1852. The Ossining Historical Society Museum.

Figure 3: “SING SING FUGITIVES TERRORIZE TOWNS, HOLD UP AUTOISTS,” New York Times (1857-1922), October 18, 1920, ProQuest, accessed October 17, 2016.

Figure 4: “HOW THE MURDERERS DIED,” New York Times (1857-1922), May 21, 1893, ProQuest, accessed October 20, 2016.