Unbelievable Escapes That Defied All Odds: 8 Prison Breaks You Have to See to Believe
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Confederate forces had seized the facilities that would become Libby Prison—once a locally owned ship chandler—early in the Civil War and converted it into what was thought to be an “escape proof” prison. But they couldn’t stop the 100 Union soldiers who banded together to break free.
The Union soldiers slowly dug a passage from the prison’s first floor to its basement, where they were then able to enter an area of the building nicknamed “Rat Hell.” Slipping into Rat Hell allowed them to avoid detection by Confederate guards while they worked for more than two weeks to burrow a tunnel from the basement into a shed on the grounds of an unoccupied lot across the street.
On the evening of February 9, 1864, more than 100 Union prisoners fled through the tunnel before the Confederate soldiers became aware of their absence at the following morning’s headcount. Nearly half of the escaped soldiers were successfully recaptured, with just 59 making it to Union territory successfully.
Ted Bundy

Serial killer Ted Bundy was arrested in August 1976 for possession of burglary tools after an officer spotted his vehicle cruising a Salt Lake City suburb in the early hours of the morning. Following his arrest, authorities began connecting Bundy to numerous unsolved murder cases across the western United States.
Bundy opted to serve as his own counsel while on trial for the murder of Caryn Campbell in 1977; he was subsequently granted access to the courthouse’s law library without handcuffs or leg shackles. While visiting the library, he slipped his inattentive guards and leapt out of the library’s second-story window. Bundy spent six days on the lam before authorities recaptured him.

Once back in prison, he wasted no time trying to hatch another plan to escape. Bundy lost a considerable amount of weight and slipped through a hole he had carved in his cell’s ceiling using a hacksaw. On December 30, 1977, he climbed through the hole and, via the ducts in the ceiling, made his way into a jailer’s apartment before donning civilian clothing and simply walking out of the prison. He ultimately made his way to Florida, where he’d claim the lives of his last known victims. He was arrested in the Sunshine State after more than a month on the run.
Bundy was found guilty of all three of the murders he’d committed in Florida. He spent just under a decade on death row before his execution on January 24, 1989.
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