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3 Infamous Prison Breaks in the Hudson Valley

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Richard Matt and David Sweat became household names this summer after their brazen escape from the upstate Clinton Correctional Facility in Dannemora. However, they are far from the only escapees in the state’s history. In fact, there have been 279 “completed escapes,” meaning the inmates left prison grounds, between 1983 and 2013, according to the Department of Corrections and Community Supervision.

Hudson Valley prisons have not been immune. Take Sing Sing, for example. The notorious maximum-security facility in Ossining has seen its fair share of creative escapes. Some prisoners left dummies in their cells, others disguised themselves as guards, and one savvy bloke even sewed himself inside a mattress that was being removed from the prison — talk about being crafty. The infamous bank robber Willie Sutton actually broke out of jail three times, the first time from Sing Sing. In December 1932, Slick Willie, as he was called, and a fellow inmate sawed right through the bottom bars of their cells. After picking several locked doors, the two climbed over an unmanned prison wall using a makeshift wire ladder, and drove off in a getaway car waiting for them on the other side. It took authorities more than a year to catch up with Sutton. 

In November 1994, three convicted murderers at Ulster County’s Shawangunk Correctional Facility escaped after cutting through their cell bars. But they didn’t get far from the prison: All three were apprehended within a few hours because they were bleeding so badly from cutting themselves on the razor wire fence surrounding the prison.  

Inmate Ernest Rickens impressed us with his escape attempt. In 1985, the nimble 24-year-old escaped from Fishkill Correctional Facility by slipping under a prison storehouse van that was delivering groceries to the facility; he wedged himself between the truck’s frame and body. But Rickens wasn’t as sly as he thought. He was discovered by the driver not long after arriving at the storehouse, and, after an intense chase, he was captured an hour later.

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