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The 5 Craziest Prison Breaks

We in no way recommend trying these techniques when you inevitably get into trouble over the holidays.


Photo: Jacom Stephens / Getty Images | Licensed to Alpha Media Group 2012

5. Ceres Prison – Goiás, Brazil (December 3, 2012)
Not-too-bright inmate Rafael Valadão surely championed the phrase “stuck between a rock and a hard place” after his ludicrous attempted prison break last week. Serving an undisclosed sentence for theft, 28-year-old Valadão and three cohorts chiseled a hole through the shower wall of their cell unit to the fresh air of freedom on the other side. The first inmate went through with no problem and escaped, but when Valadão entered the hole, his fat ass got stuck halfway through - so much so that the two inmates behind him, in a display of that famous convict hospitality, tried to force him through and fractured one of his ribs. Valadão started screaming in pain – which promptly alerted the prison guards – and the jailbreak was over. So we guess halfway crooks do exist.

4. Union County Detention Unit – New Jersey (December 15, 2007)
Otis Blunt, 33, was facing 20 years for robbery, and his 19-year-old accomplice, Jose Espinosa, was sentenced to 17 years for aggravated manslaughter. Less than keen on these sentences, the two launched an escape, repeatedly using a water valve over three weeks to bust through the bricks and mortar of their neighboring cells. During the interim, they obscured the holes with cutouts of scantily clad women (we’re really hoping they weren’t Maxim girls). Once outside, they jumped from a third floor roof over razor wire-topped fence – a distance of 15 feet with a 32-foot drop. Remarkably, they both cleared the jump, but Espinosa fractured his ankle in the landing. After being on the lam for three weeks (and appearing on America’s Most Wanted), Espinosa was found hiding in plain site in a basement apartment just a half-mile away. Blunt, however, proved to be far more cunning, making it all the way across the border before U.S. Marshals found him in a cheap hotel in Mexico City. Admit it - you can almost hear Morgan Freeman’s voice while you read this story.

3. Chetumal Prison – Mexico (July 5, 2011)
We’ve heard of police bagging criminals, but never criminals bagging themselves. That’s literally what drug trafficker Juan Ramirez Tijerina did in one of the dumbest escape attempts of all time: After an overnight conjugal visit with his 19-year-old wife, Maria del Mar Arjona, Tijerina stuffed himself into Arjona’s black-wheeled suitcase and she casually headed toward the prison exit. But when she struggled with the bulky bag on some stairs, guards noticed something moving inside and stopped Arjona. They unzipped the suitcase to find Tijerina curled up inside in the fetal position. We’re assuming the food at Chetumal prison must be really, really bad.

2. Everglades Correctional Institute – Florida (April 11, 1998)
There’s nothing stronger than a mother’s love for her child, especially if that child is serving 20 years in jail for armed robbery. Jay Junior Sigler, 31, was eight years into his hard-time sentence when his doting mum, 58-year-old Sandra Sigler, had two accomplices barrel through multiple security fences at the prison with a big-rig tractor, while she followed close behind in an Oldsmobile Cutlass Supreme. Jay hauled ass from inside the jail, jumped inside mommy’s Cutlass with the two other daredevils, and all four drove off into the swampy sunset before prison guards could even get a shot fired. Of course, they were all caught just two days later, but Mama Sigler gets a gold star for being the baddest parent who ever lived.

1. Lecumburri Prison – Mexico (December 17, 1975)
American Dwight Worker was sent to a foreign prison after being arrested in Mexico City in 1973 for attempting to smuggle cocaine. Sentenced to five years in what’s infamously known as one of Mexico’s most brutal prisons, Worker barely survived two years of torture, electroshock treatment, and four stabbings before deciding he’d had enough. He had his wife smuggle in a wig, makeup, women’s clothing, and fake identification during one of her visits, and Worker casually walked out of the prison as just another female visitor. To this day, Worker still remains a free man in Indiana, where he formerly taught at the Indiana University Kelly School of Business for ten years. Not surprisingly, he has said, "That was the first, second, and last time I will ever wear a dress."

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