Shortly after a man named William Green escaped from Sing Sing prison (approximately 30 miles North of Manhattan in Ossining, NY) the Sunday Magazine took a look at how so many people have managed to escape from Sing Sing. It turns out that the prison was so overcrowded that it wasn’t difficult to slip away. Sing Sing was built to accommodate 1,200 prisoners, and at this time of Green’s escape there were more than 500 above the limit.

The escape of Green’s was more or less of a novelty. The usual course has been to make a rush. But Green, in the most leisurely manner in the world, attacked the two keepers in charge of the dormitory, laid them out, then took out a saw which he had secured somewhere, sawed at a window for twenty minutes, invited his fellow-convicts to join him, was reinforced by four of them, dropped out of the window, and disappeared.

The article recounts other noteworthy Sing Sing escapes, including Thomas Pallister and Frank W. Roehl, two convicted murderers, who escaped in 1893. Pallister overpowered a guard and took his gun, cap, shoes, and keys, and then unlocked the cells of other prisoners.He and Roehl broke out of the prison through a skylight, but “it was an unfortunate escape for them, for a few days later one of them shot the other in a quarrel and then committed suicide. But in the meanwhile they had baffled all the efforts of the State to recapture them.”

THE WAYS IN WHICH MEN ESCAPE FROM SING SING: Green’s Success Was Due to Congestion of the Prison — How Roehl and Pallister Escaped — A Rush the Usual Method (PDF)

From October 16, 1910