Four men conspire to break out of one of the most notorious prisons in American history. Three make it to the water's edge... but what happened to them when they left the island remains a mystery to this day.

Stuck in prison on life sentences, two men used engineering smarts and psychological manipulation of several prison employees to escape Dannemora Prison; Richard Matt and David Sweat executed one of the most involved escapes from an American prison.

Timothy Vail and Timothy Morgan were murderers incarcerated at Elmira State Prison in Elmira, N.Y.;. Vail wanted to escape, so he engaged Morgan in his plan to dig through the ceiling and flee from prison.