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Two of the prisoners were working on the railroad which cut through the prison yard.

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. Other prisoners involved in violent, multi-person escape attempts were able to work together without such fatal ends. 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. The second article included theories about how they might have gotten away successfully on a boat. The New York Times covered the initial news, and then released a second article, also written before the men were found in 1893. 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. Most of the prison officials agreed that they ended up fighting and killing each other. However, at the end of the two weeks, the men were found dead. The search for the escapees went on for two weeks, which would have given them a great deal of clearance. 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 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 duo continued on alone, climbing up and cutting a hole in the roof. Although Roehl and Pallister had masterminded the plan, the men stopped and asked another death row inmate to join them, but he declined.

Roehl stole the keys and pistol from the keeper, then freed Pallister.

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. The men were both awaiting the electric chair, and seemingly decided that escape was the only option.