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VOICE OVER: Peter DeGiglio WRITTEN BY: Willow McLaughlin
These prison escapes will leave you speechless! For this list, we'll be looking at the most audacious, ingenious and outrageous jailbreaks captured on video. Our countdown includes Houdini in Handcuffs, Food Goes In, Prisoner Goes Out, Inside Help, and more!

#10: You Left the Keys in the Ignition?

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WKEF For a prison guard, being able to count convicts is an essential skill. When Donald Knisley arrived with his fellow inmates in the prison garage, he noticed that the officers weren’t paying close attention. While the others were filing into the building, Knisley ducked behind the van. His luck was running high because nobody noticed he was missing. On top of that, the keys of the transport van were still in the ignition. The bold criminal hit the gas and drove right through the garage door… and eventually into a line of trees. The officers shortly had him safely behind locked doors. It goes to show that just because you have the keys to the van, it doesn’t mean you can actually drive it.

#9: Houdini in Handcuffs

ABC News Unless you know some nifty magic tricks, it’s generally assumed that handcuffs are difficult to get out of. A Wisconsin woman didn’t seem to think they were a problem. Amber Gonzales was left alone in a holding room reportedly to arrange for bail on a cell phone. With just a little bit of effort, she was able to wiggle out of the restraints. Then, Gonzales took keys from the door and used them to get to an emergency exit. She was later found at the same hotel from which she was arrested. The guards claimed they put the cuffs on very tightly. Maybe they just didn’t expect a small woman to have tiny hands.

#8: Perfect Timing

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WXIN It takes some spectacular timing to make it through a heavy door that’s about to seal shut. When he arrived at the prison garage, Michael Maldonado decided it was worth the risk. He jumped from the back seat of the police car to the front and out the driver’s side door. Then, he ducked underneath the garage door just as it was closing. The officers had to reopen the door before they could pursue. In the footage, Maldonado can be seen sprinting across the parking lot. It took a full day for them to track him down. It goes to show that when someone’s chasing you, a person can indeed be motivated to run very fast.

#7: Inside Help

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WXIN Most of the time, when you hear about a prison escape, you assume they had a complicated plan. Let’s face it though: only someone like Tom Cruise would have someone in place to just open all of the gates for him. Well, for three inmates in New Mexico their escape was just that simple. The footage shows the inmates walking easily through all of the jail’s doors and gates. It was assumed that someone helped them make this simple escape. The footage, which shows an on-duty female officer looking extremely stressed, pointed to the culprit. She was later arrested as an accomplice in their escape. The three inmates were returned to jail a few days later. Now their outside help was on the inside.

#6: Guess We Should Close That Window

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KARK-TV It can be so irritating when there’s nobody manning a reception desk and all you see is an empty window. What would be frustrating for an average person was the perfect opportunity for an inmate in Arkansas. Derrick Estell was having a telephone conversation in a visitation room. One of his fellow inmates made inquiries of the guards. They left the room to figure things out. With the area left unsupervised, Estell dove through the reception window to make his escape. His girlfriend was waiting outside in a car and his escape was complete. They were both eventually apprehended and Estell had an extra 40 years added to his sentence. Maybe not such a fortunate opportunity after all.

#5: If at First You Don’t Succeed…

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Alter Escaping prison by helicopter is a fairly impressive feat. How about doing it twice? Vassilis Palaiokostas was known as “The Greek Robin Hood'', because he gave the money he stole to those who didn’t have as much. It was quite a media sensation in 2006 when he escaped his 25 year prison sentence. Two of his friends rented a tourist helicopter and made the pilot land in the prison yard. A year after he was returned to prison in 2008, Palaiokostas escaped again in almost exactly the same way. This time they climbed a rope ladder to the helicopter to escape. His accomplice Alket Rizai was captured and is serving out his prison time. Palaiokostas is still free and has since been dubbed, “The Uncatchable.”

#4: Freedom or Fame?

KNBC Most prisoners would prefer that there be no evidence of their escape. Not these three inmates from California, however. They filmed their entire breakout on a contraband cell phone. The video shows them crawling into a vent. They climb through plumbing tunnels to the rooftop. Although their method of getting to the ground wasn’t filmed, they later claimed to use a rope. They kidnapped a cab driver who drove them to where they had a van set up with supplies. The three escapees were picked up by police while chilling in their mobile hideout. They turned the footage into an edited video with music and voice overs bragging about their deeds. Was having their selfie video online worth the extra time in jail?

#3: Food Goes In, Prisoner Goes Out

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Yahoo! News When you think of a prisoner locked up alone in a prison cell, you can’t help but also picture the food door. That open space in the door is narrow so that the food can go in, but the prisoner can’t get out. Well, one particularly agile prisoner in Russia wasn’t about to let that stop him. The prison footage clearly shows him squeezing his body through the tiny food hatch. He gets stuck for a moment, but manages to wiggle his way out. All that’s left to do was put on his clothes and calmly exit. It’s an astounding feat, but it took a couple minutes. Why didn’t anyone see it on camera? What were the prison guards doing?

#2: Spared No Expense

VICE News Worried that he would be extradited to the U.S., Joaquín “El Chapo” Guzmán decided to leave his prison cell behind. His family and friends built a mile-long tunnel that connected to the shower of Guzman’s cell. The prison footage shows him putting on his shoes and then disappearing behind the low shower wall. Evidence suggests that he then used a motorcycle on rails to travel to the end of the well-lit tunnel. It’s hard to imagine that the construction of the well-equipped escape route would have gone unnoticed. Was it a true breakout? Or was it well-orchestrated drama to hide the involvement of the prison security? We may never know.

#1: That Was Unexpected

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TV 2 Why plan an escape that only lets out one prisoner, when you can create ultimate chaos and release many more? Nobody knows who planned this tumultuous escape, but it was simple and effective. In 1995, a bulldozer slammed into the wall of a Danish prison. A TV crew showed up just in time to film between twelve and thirteen prisoners running away in a cloud of dust and debris. The police detained one of the cameramen, because the timing of their arrival seemed suspicious. Only 3 of the escapees were ever caught. It’s also unclear if anyone was driving the bulldozer when it slammed into the wall. It could have been a machine uprising. But more likely, the driver escaped in the chaos.

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