Sing Sing's long history of ingenious escapes

OSSINING – Last week's escape from the Clinton Correctional Facility by two murderers who cut through cell walls and crawled out of a manhole has invited comparisons to Frank Darabont's "The Shawshank Redemption" — but Ossining's notorious Sing Sing Correctional Facility provides plenty of examples of real-life breakouts rivaling anything Hollywood can dream up.

Since opening in 1826, the prison "up the river" from New York City has seen dozens of escapes and escape attempts, using a variety of sometimes ingenious methods. Some escapees left dummies in their cells, others disguised themselves in guard uniforms to try to slip out and one man even sewed himself inside a mattress that was being removed from the prison.

Willie "The Actor" Sutton, who famously robbed banks "because that's where the money is," broke out of jail five times in his career. His first escape, in 1932, was from Sing Sing, when he used a makeshift wire ladder to scale an unmanned wall.

(More notable escapes farther down in this story)

"Sing Sing captures people's imagination," Ossining police Capt. Scott Craven said. "It's close to New York City, it's been in a lot of movies and it's got that unusual name. It's instantly identifiable around the world."

Still, he said, there's nothing romantic about prison escapes, noting that in 1940 three Sing Sing inmates shot and killed guard John Hartye as they escaped and, once outside, killed Ossining Police Officer James Fagan. One of the trio was killed in a shootout; the other two were captured after seven hours on the lam.

Almost 75 years later, Ossining police still participate in a ceremony held at Sing Sing each April to honor the slain officers.

State corrections officers and state police are responsible for dealing with prison breakouts, but the Ossining Police Department has contingency plans for handling escapes from the prison, Craven said.

"This is not Shawshank Redemption," Craven said. "The people in state prisons are really bad guys."

The above video shows the funeral of Ossining Police Officer James W. Fagan, who was shot and killed on April 14, 1940, during a prison escape from Sing Sing. The Ossining Police Department posted the funeral footage on YouTube.

Between 1983 and 2013, officers in New York state dealt with 624 escapes or attempted prison escapes, according to the Department of Corrections and Community Supervision.

Of those, 279 were classified as "completed escapes," meaning the person made it off prison grounds, with 31 breakouts the most in one year, in 1994. Escapes have decreased significantly since that time, averaging just three to four attempts per year and two actual escapes in New York from 2009 to 2013.

Nationally, there were 2,000 escapes from state correctional institutions in 2013, compared to more than 14,000 in 1993, according to the federal Bureau of Justice Statistics.

Sing Sing's extensive history of escape attempts might be explained by a former inmate who used the alias "Number 1500" in authoring "Life in Sing Sing," in 1904. He described it as "perhaps the most insecure prison, structurally, that was ever built," citing the proximity to the Hudson River and the location along the railroad tracks connecting to New York City as easy avenues for fleeing the area.

The author said there had been "40 or 50" successful escapes in his 20 years incarcerated at Sing Sing.

Notable Sing Sing prisoner escapes and attempts include:

• 1872: When both men and women were housed there, a man escaped in a horse carriage. Fifteen days later, his wife escaped in the same carriage. Almost 50 years after that, the woman wrote the warden a letter saying she was living well in Detroit. Included in the letter was a $500 check.

• 1875: Five men hijacked a freight train that was passing the prison. After nearly running the train into the river at Scarborough, they got away. Four were caught, but one made a successful getaway to England, where he opened a pub.

• 1930: Jack Levy, 45, sewed himself into a mattress that was being thrown away. His attempt was foiled when the prison keeper noticed a lump in the mattress.

• 1938: Everett Bellach, 25, jumped from a train at the Riverdale station on his return trip from his mother's funeral. The first inmate to violate the funeral honor system, he was caught later that day.

• 1964: Seymour Snyder, 48, broke a streak of 14 escape-less years at Sing Sing when he ran off while on a work-release program. He was captured nine days later on Long Island.

• 1986: In the most recent escape, Julio Giano, Thomas Linz and Darius Gittens created a distraction with homemade smoke bombs, then scaled the wall using a 30-foot rope made from leather shoelaces. They were all caught within 30 hours.

The last known escape attempt happened in May 2003, when two men — Nicholas Zimmerman, 27, and Steven Finley, 26 — had several accomplices both inside and outside the prison help with their plan. The men had conspirators show up with fake IDs and guard uniforms, but their plan was foiled at the gate.

Staff writer Richard Liebson contributed to this report.

Sing Sing goes Hollywood

Sing Sing has long captured the imagination of filmmakers. Here's a sampling of some of the movies starring "the big house."

"The Big House," 1930, starring Robert Montgomery.

"Up the River," 1930, starring Spencer Tracy, Warren Hymer and Humphrey Bogart.

"20,000 Years in Sing Sing," 1932, starring Spencer Tracy, Bette Davis and Arthur Byron.

"Angels With Dirty Faces," 1938, starring James Cagney and Pat O'Brien

"Analyze That," 2002, starring Robert De Niro and Billy Crystal.

Thinly veiled versions of the prison even show up in cartoons: 1950's "Big House Bunny," stars Bugs himself mistakenly tunneling into "Sing Song" prison while trying to evade hunters.

In Episode 24 of the "The Dick Tracy Show" in 1961, the cartoon features the detective with a two-way radio wristwatch to capture two desperadoes who escape from "Sing Song" prison.