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10 Insane Prison Escapes!

324 views · Published 29 September 2017 · 13:06 · Indexed 12 October 2026

Channel: Zero2Hero · 2017 · Entertainment

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10 Insane Prison Escapes! Throughout history, men and women have been incarcerated for crimes that they did, or sometimes didn't commit. While most allow the wheels of the justice system to turn, THESE criminals decided to take things into their OWN hands and bust out.

This is a list of world famous, insane prison escapes, investigations, and police chases of criminals after they decide to release themselves from prison. Some are still on the loose in 2017!

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From tricks that should never have worked, to very adamant mothers. This is our list of the top ten most daring and insane prison breaks ever!

10. Ted Bundy’s Books
Ted Bundy is no joke. He’s one of the most famous serial killers of the past couple generations. Bundy terrorized the thoughts of honest Americans during the early sixties and late seventies. All in all, Bundy’s victim-count numbered above thirty people. 
Many of the killer’s victims described Bundy as handsome and charismatic. But, to put it plainly, he was a sociopath -- albeit one who was a good talker.Still, even the best of orators and most confident of criminals generally allow a lawyer to do the talking for them in court, but not Bundy. 
The serial killer actually waived his right to legal representation during a trial in a Colorado courtroom.Representing one’s self in court might sound like something that an over-confident sociopath might very well do, but Bundy hadn’t opted for this option out of pride or vanity. 
Whether the man had predicted it would happen or not, once Bundy had been brought into the courtroom the officer’s present allowed him to move freely without handcuffs to better represent himself before a jury and judge.It’s never a good idea to trust a serial killer, though, and Bundy would go on to prove that. During a recess in his trial, the man requested that he be allowed to visit the courthouse’s library of legal books. 
Bundy’s request was surprisingly granted and the killer was allowed to make his way to the legal building’s collection of law tomes. Once in the library, perhaps as should have been expected, Bundy dove from the room’s two-story window and escaped to his freedom.Bundy would go on to make numerous other escapes from the law, before finally being put down years later. 
Bundy actually stated that he had intended to give up serial killing after this escape, but unfortunately, he just couldn’t resist whatever twisted urge had driven him to his crimes in the first place.
9. A Mother’s Love
Jay Junior Sigler was an inmate that had been convicted of armed robbery and sentenced to twenty years in prison for his crime. 
Jay was on the eighth year of his sentence when his family finally decided that they’d had enough of their relative being imprisoned.Now, what happened next was like something pulled straight out of an over-the-top action movie. Jay’s mother and two of the convict’s friends attacked the prison in broad daylight. 
How did they do it?Well, with an 18-wheeler and lots of firearms of course. Jay’s closest friends and family took the massive truck and rammed it at full speed through a total of four prison fences.Jay’s mother then followed the truck in an Oldsmobile Cutlass Supreme.Once his rescue party had breached the gates of his prison, Jay himself quickly made his way to his mother and her getaway car, but not before being tossed a scatter by the same friend who had driven the aforementioned 18-wheeler into the prison yard.A full on fight ensued between Jay, his family, and the guards of the prison, while Jay, his mother, and his friends made their escape. 
Fortunately, the escaped convict and his entourage only made it about forty miles out before being hauled away in chains, but not before they’d tragically taken the life of an unlucky fifty-five year old man in a hit and run collision.
8. London’s Spectacular Showman 
Con men have garnered a bit of a reputation for being incredibly smooth and charismatic -- even if at the end of the day they’re generally disapproved of by society at large.Every generation has their famous and infamous law breakers and in the 18th century the title of “most dazzling vagabond” definitely rested upon the shoulders of a man named Jack Shepherd. Shepperd was known for attracting crowds thanks to his ability to make flashy and dashing escapes from his trials and holding cells. 
During his first escape, Shepperd loudly cracked open the ceiling of his prison cell and then scaled down the walls of the jailhouse he was being held in.After his second escape from prison, and after being caught a third time by authorities, the guards of the NEW prison he’d been shipped off to were in no mood to take chances with Jack. They wrapped the man in chains, bound him in a number of ways, and then locked him behind three reinforced doors.

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