Sing Sing Prison, Ossining, NY: A History of Hudson Valley’s Jail Up the River

One of America’s most infamous prisons, Sing Sing has been housing criminals for nearly 200 years

The natives who lived there called themselves the Sint Sink, which meant “stone upon stone.” The 17th-century Dutch interlopers appropriated their land and altered the name to Sinck Sinck or Cinque Singte. In the mid-1800s it became known as Ossin-sing, from another Native American word, ossin, also meaning stone.

But criminals have always called it “up the river.”

Sing Sing, the prison, and Ossining, the town, are inextricably linked. Indeed, in 1902 the town changed its name only because the prison had become so notorious. And that’s just one of a multitude of facts, stories, and myths surrounding this nearly 200-year-old star of stage, screen, song — and grisly executions.

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Its age was one of the things that inspired Guy Cheli, a writer who lives in Mahopac, to research and write Sing Sing Prison, a book in the “Images of America” series published by Arcadia Publishing in 2003. “It was built in 1825, and there aren’t many things still standing now from 1825,” says Cheli, 58, a member of the Ossining Historical Society. Like many who work or live in the region, Cheli was aware of the prison but not its history. “It’s right there in Westchester County,” he says, “but I never really knew the story behind it.”

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» Visit Sing Sing Prison Visitor Center in Ossining, NY
» Visit Ossining Historical Society in Ossining, NY


sing sing prison aerial viewThe prison sits on the banks of the Hudson, making escape more difficult

Photograph courtesy of Library of Congress Prints and Photographs Division

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You dirty rat…

The name Sing Sing almost immediately conjures images of the gangster era of the 1920s and ’30s, of Jimmy Cagney movies and cops-and-robbers radio serials. During that time the prison housed the infamous Willie Sutton, Lucky Luciano, members of Murder Incorporated, and other well-known ne’er-do-wells. But by then, bad guys had been sent “up the river” from New York City courthouses for 100 years.

When New York State’s first two prisons — one in Greenwich Village dating from 1797 and the other in Auburn built in 1816 — became overcrowded, the Legislature commissioned Auburn Prison warden Elam Lynds to build a new and more modern prison. He decided to locate it in Mount Pleasant, near a small village called Sing Sing, because the stones implied by its name were still being quarried nearby.

In 1825, Lynds transferred 100 Auburn inmates by barge along the Erie Canal to freighters that took them down the Hudson to Sing Sing, where he forced them, at gunpoint, to build the new prison. It opened in 1826, and was fully built in 1828. The completed cell block was four tiers high. Each cell was seven feet deep, 39 inches wide, and about six-and-a-half feet high. But with crime a growth industry, it continued to expand for the rest of the 1800s. By the turn of the century, it housed more than 1,200 prisoners.

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» Visit Sing Sing Prison Visitor Center in Ossining, NY
» Visit Ossining Historical Society in Ossining, NY

electric chair
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“Old Sparky” was the name given to the electric chair, first used at Sing Sing in 1891

Photograph courtesy of the Ossining Historical Society

Old Sparky

A 19th-century prison was a barbaric place, and Sing Sing was no exception. Prisoners were expected to keep absolute silence. Beatings — and worse — were commonplace. “Bread and water” and “ball and chain” weren’t euphemisms, they were a way of life. According to Mark Gado, the author of Stone Upon Stone: Sing Sing Prison, “the bath” was a method of torture used for decades to terrify the population and maintain order. “An inmate was tied to a chair… Water was dropped in a steady stream from a great height and landed on the top of a prisoner’s head. Prison records show that 170 men received this punishment in 1852. That same year, 120 men were placed in solitary confinement and five were “bucked”… causing the man to hang upside down like a roasted pig.”

“There really was torture,” says Cheli, until prison reform took hold in the country, led in large part by Lewis Lawes, Sing Sing’s warden during the ’20s and ’30s. “Lawes believe that prison was punishment enough, and that he would send prisoners back into the world as better people than when they came in,” Cheli says. Lawes educated prisoners, taught them trades, and entertained them with visits from the likes of Babe Ruth, Harry Houdini, Edward G. Robinson, and other stars of the day. “He helped change the way prisons were run,” says Cheli.

Lawes also abhorred the death penalty, which propelled Sing Sing into the spotlight many times during its history. Sing Sing electrocuted its first prisoner in 1891. By 1916, all of New York’s electrocutions took place there. The first woman to be executed by the electric chair also occurred at Sing Sing in 1899. Martha Place had been found guilty of murdering her stepdaughter. The electrocution of Ruth Snyder in 1928 for the murder of her husband was made famous when a photographer for a New York City tabloid smuggled a hidden camera into the death chamber and photographed her in the electric chair as the current was turned on. But perhaps the most famous execution at the prison was that of Julius and Ethel Rosenberg, convicted of espionage, in 1953. They were two of a total of 614 men and women who were put to death in the electric chair, known as “Old Sparky.” In 1963, the last execution was conducted in New York.

(Continued on next page)

» Visit Sing Sing Prison Visitor Center in Ossining, NY
» Visit Ossining Historical Society in Ossining, NY


sing sing prison todayHard time: A modern-day view of the prison wall and watchtower

Rooms with no view

Today, Sing Sing houses about 2,000 inmates as a maximum-security prison. But it’s essentially hiding in plain sight. Its impact on the village has been minimal. “It has supplied jobs, but many of the workers don’t live locally anymore,” Cheli says. There have been only a handful of escapes. In 1980, prisoners held some guards hostage. “Most famously, in 1941, a village police officer and a corrections officer were shot and killed during a prison break,” Cheli says. The escapees were caught and executed.

The prison may come out of hiding, however, if plans for a museum and visitors center ever come to fruition. “In my opinion, that would be great,” Cheli enthuses. “The train from Times Square goes right past it. Imagine how many millions of people would go there — it could be like Alcatraz. It would be a boon for the village and the state.”

Cheli is biased, of course. “Sing Sing is my favorite subject that I ever covered,” he says. In fact, he has a personal collection of artifacts, including old books, photos, artwork, and letters from wardens and prisoners, some of it more than a century old. “I have a beaded necklace made by a prisoner in the late 1800s,” he says. “It looks like a Native American necklace.”

But his collection isn’t open for public viewing. As of now, only the Caputo Community Center in Ossining, which has a small exhibit, and the Ossining Historical Society — which is more library than museum — openly acknowledge the place where bad guys go when they are sent up the river.

» Visit Sing Sing Prison Visitor Center in Ossining, NY
» Visit Ossining Historical Society in Ossining, NY

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