Sing Sing

“The Sing Sing Correctional Facility sprawls across fifty-five acres of the east bank of the Hudson River, some thirty miles north of New York City,” wrote Ted Conover. “Convicted criminals used to travel from the city to Sing Sing by boat ‘up the river' to ‘the big house,' which is how both phrases entered the language” (Conover 2000a). Conover, a journalist, worked for a year as a guard at the prison and wrote about his experiences in the book Newjack. He is one of many officials, inmates, and observers who have chronicled their observations and experiences at one of the nation's oldest penal institutions. Sing Sing has been in continuous use since 1826.

Originally known as Mount Pleasant Prison, Sing Sing Prison was constructed above the Hudson River in New York to provide additional prison space and to replace Newgate Prison. Construction was undertaken by Elam Lynds, warden of Auburn State Prison, in 1825 and completed by convict laborers in 1828. The initial facility had 800 cells. The prison population jumped in 1860, resulting in more construction. The four-story complex was soon six stories.

One of the notable visitors to the prison was Alexis de Tocqueville (1805–1859), author of Democracy in America. The French government sent him and Gustave de Beaumont (1802–1866) to the United States in 1831 to gather information about the American penal system. The two men were amazed at the total subjugation under which prisoners worked and the administrative power Lynds wielded at Sing Sing.

“One cannot see the prison of Sing-Sing,” these men wrote, “and the system of labor which is there established without being struck by astonishment and fear. Although the discipline is perfect, one feels that it rests on fragile foundations: it is due to a tour de force which is reborn unceasingly and which has to be reproduced each day, under penalty of compromising the whole system of discipline” (quoted in Pierson 1959: 68).

Lynds resigned as warden of Sing Sing in 1830 and returned to Auburn in 1838. He was asked to leave that prison a year later after the death of a prisoner who was punished severely for feigning illness. Despite this record, Sing Sing rehired Lynds in 1843.

Whippings and floggings were commonplace punishments. Frequently used was the cat-o'-nine-tails, a notoriously cruel whipping contraption whose lashes were often tipped with metal or barbs. Its use was abolished by the New York State legislature in 1848.

With the advent of the electric chair in 1891 Sing Sing became notorious for its executions. Although the electric chair was developed at neighboring Auburn, almost all executions within the state were carried out [Page 1518]at Sing Sing until 1963. The infamous “death chair” was later moved to Green Haven prison.

Sing Sing was also the site of penal reforms that affected the national penal system. Reformer Thomas Mott Osborne, who developed his penology theories while voluntarily incarcerated for a year at Auburn, was appointed warden in 1914. But his immediate, sweeping changes were assailed, and he resigned the next year under intense political pressure. During his tenure, however, the first psychological work with inmates began.

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