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Top 8 Most Daring Prison Breaks In History

If you like stories about legendary criminals escaping from impossible-to-escape places, or even if you just enjoyed watching Prison Break, you are in for a treat. There is something heroic and even romantic in regard to a story of a man who managed to plot an escape for month or even years. You certainly have to be brave or reckless at least; however, it takes patience, strong nerves, and creativity—apart from having the courage and the right type of character—to successfully escape a high-security prison.

We’ll start off with an additional story about a recent escape of three prisoners from a Californian facility. The interesting part is they actually managed to film their prison break.

It looks exactly like how it would happen in the countless movies we have all seen—some inmates dressed in the typical jail suits take off the ventilation shaft grill, crawl inside, and then start making their way through the narrows of the building. They even had to cut steel bars on the way to freedom. But the footage is as real as they get. It was released by lawyers in California, who were probably just as stunned when they saw the Shawshank-style escape from the maximum security prison in Orange County. It happened back in 2016, and nobody has a clue about how they managed to get their hands on everything they needed in order to execute the plan, including the phone they used to film the whole thing. One thing is for sure—they had to be inspired a lot by the movies.



Adam Hossein Nayeri, Bac Duong, and Jonathan Tieu were the three inmates who made the video. They somehow managed to find a way through the wall of their cell, cutting through steel bars and even using bed sheets as ramps. When they found themselves outside, they got into a white van and drove off, pulling off a truly successful jailbreak. After spending some time running and living in the van—only sustaining themselves on water, bananas and some marijuana—one of the men decided to turn himself in, and this led to re-arresting the other two. The attempt of the trio is among the last of a long list of daring jailbreak attempts, some of which were not successful, but really worth sharing.

1. El Chapo Is A Hard Man To Apprehend

One of the most discussed legends in Mexico has to be El Chapo’s ability to evade being captured time after time. When he was finally apprehended in 2015, after hiding for thirteen years, Joaquin Guzman—nicknamed “El Chapo” (literally meaning Shorty)—fled the prison facility he was put in after just a little more than a year behind bars. His escape was also worthy of a Hollywood movie; he managed to escape through a tunnel which was about a mile long, stretching from his cell to a construction site outside of the prison borders.



You could image the authorities’ response to this. They organized a manhunt, with a lot of people involved, in order to catch the Osama bin Laden of Mexico—as El Chapo is also known. Flights were canceled; many of the main roads were blocked. Eighteen members of the prison staff were questioned thoroughly to determine if they had any connection to the daring escape.

Eventually, El Chapo was apprehended again, but not before he got to spend some time with actor Sean Penn. The gangster is currently behind bars, and could be planning his next escape while you are reading this. He is set to be tried in April of this year, and we have yet to hear about any sort of possible sentence.

2. The Shawshank Redemption Reinvented

And while El Chapo’s jailbreak is completely in the style of The Shawshank Redemption movie, it is not the only one to be worthy of comparing to the Hollywood masterpiece.

In the middle of 2017 two inmates in America managed to successfully break out from prison after cutting through the steel walls with the help of power tools.

48-year-old Richard Matt and 34-year-old David Sweat crawled through a series of tunnels on their way out of the Clinton Correctional Facility, located in Dannemora. The two convicts were in prison for murder. They reportedly left a note to the guards, wishing them to have a nice day. But you have probably watched the original movie and know what happens to the main character. Unlike him, the duo in this story had only a limited time to enjoy their freedom.

After just 20 days outside and being constantly on the run, Matt was shot and killed, and Sweat was found two days later; he then returned in jail.

3. Escaping The Impossible

When we talk about prisons, there probably isn’t a single person that has not heard of the name Alcatraz. The legendary federal maximum-security prison is built on a very small island located off San Francisco’s coast. It was constructed with the idea that it would be impossible for escape. However, three men decided to see for themselves if that was true. Their 1962 escape was remarkable and was the inspiration for a Hollywood movie.

The brothers Clarence and John Anglin and fellow inmate Frank Morris were behind bars for a number of crimes, including bank robbery and grand theft auto, when they actually escaped from the claustrophobic cells of Alcatraz. The men managed to cut holes in the walls—and they even built dummy bodies to trick the guards into believing there were people sleeping in the cells.

The trio got out of the building through the ventilation shaft and successfully climbed the prison wall. Soon they vanished in the San Francisco Bay around 10:00 p.m. by utilizing a raft made out of raincoats and cement.

The Anglin brothers and Morris were not found afterwards, and nobody heard from them after the daring escape. The FBI’s investigation simply stated that the strong current and the cold waters took their toll, and the little group likely drowned. However, there is a slight chance that they got to the mainland, and the 1979 movie Escape from Alcatraz questions the report’s conclusion, suggesting that the trio may have actually survived and lived another day after their feat.

4. The Legendary Con Man

Speaking of Hollywood and jailbreaks, the present list would not be complete if Frank Abagnale’s name is not mentioned—he just happens to be the famous fraudster whose story was told via the 2002 movie Catch Me If You Can.

Abagnale was able to commit a long list of unbelievable crimes. For example, he managed to fly more than a million miles before he turned 18 years old—he did that by pretending to be a Pan Am pilot. The criminal always secured a place in the cockpit, although he always took the spare seat; however, he was still left in charge of flying the whole plane when the main pilot needed to go to the toilet.

Abagnale has an amazing prison escape in his criminal history, which he describes in detail in his autobiography. At one point he received a 12-year sentence in the US, and during his transportation to the facility, the Marshall that was escorting him happened to forget all the papers of the prisoner, which was a stroke of luck; Abagnale immediately took advantage of the situation and was able to convince the guards that he was a prison inspector who went in undercover. This was a common practice used by the authorities back then to test if the prison rules had any flaws—so the guards were easily fooled.

Frank Abagnale also wrote that he received a much better treatment in jail compared to the other prisoners because of his “status” as an undercover agent. The plan’s culmination involved the assistance of a friend—who Abagnale refers to “Jean Sebring” in his book. Sebring managed to fabricate and smuggle inside the prison two business cards—one was a FBI agent’s and the other one was a prison inspector’s. Abagnale almost immediately told the guards that he needed to speak with the FBI agent. When they dialed the number, Sebring was on the other side of the line. She told them that she had to meet him outside of the prison premises, and the con man was able to walk out of the main prison entrance. You could probably imagine how he felt and the expression he had on his face.

5. The Freedom Key

Great Britain’s answer to Alcatraz was the Parkhurst prison, built on the Isle of Wight. However, there were three men that thought breaking out of the facility was possible, and they carefully planned their escape.

Matthew Williams, Keith Rose, and Andrew Rodger were convicted after the heavy crimes they committed, including murder and planting a bomb. On a cold January evening in the beginning of 1995, they managed to escape using a key they had cut themselves.

The trio used the key more than once—they managed to open a series of doors, after which they cut a mesh fence and climbed a wall. Once out of the prison perimeter, they hired a cab to take them to Sandown, a small town where they spent the following four days in attempt to steal a plane or a boat. During that time, they slept in the field. They were eventually found by a prison officer who was not on duty at the moment.

The successful escape of the trio caused Parkhurst’s security level to be downgraded.

6. The Yoga Master

The most unique jailbreak was probably the one executed by Choi Gap-bok. The yoga practitioner used some unique methods for his escape, which certainly found their place in the history books. He did not dig a tunnel or manipulate the steel bars of his cell, but used his skill instead—he managed to literally slip himself through the opening at the cell door bottom, usually used to serve food to the inmates. The whole act lasted exactly 34 seconds.

When the convict was captured six days after his stunt, he was put in another cell that had a smaller opening in the lower part of the door.

7. An Escape That Saved Many Lives

Alfréd Wetzler is a man who managed to flee out of Auschwitz death camp created by the Nazis, and it proved to be one of the most important jailbreaks ever.

Wetzler was a Slovakian Jew who was able to escape Auschwitz with the help of his fellow Rudof Vrba. They successfully escaped from the concentration camp inside a pile of wood that the other inmates had previously soaked in gasoline and tobacco—so the guard dog would not be able to detect them. They spent four nights under the pile, and later they dressed in stolen suits and overcoats and started the journey to the Polish border near Slovakia, which was about 80 miles.

Wetzler had a detailed report of everything concerning the death camp—ground plans, gas chambers, and all the secret rules. He also got a label from a can of Zyklon B gas—the same that was used by the Nazis to eliminate millions of prisoners. The Allies thought that the report was incredible since it contained information about Auschwitz that was not available until that moment. The report helped to plan the bombings of all the buildings used by Nazi officers to control the railway deportation of people. As the result of all these actions, approximately 120,000 Hungarian Jew were reportedly saved from deportation to the concentration camp.

8. The Helicopter Jailbreak

Pascal Payet is a French man convicted for murder. He became notorious after a series of movie-like escapes using a helicopter.

Payet’s first attempt to break out was in 2001 when he organized his friends to pick him up from the prison roof in a helicopter. Believe it or not, he managed to pull off the same stunt again two years later and picked up three more fellow convicts.

Later, he was caught and got a 30-year sentence for a murder he committed in 2005. After all the jailbreaks he was involved in, authorities kept an eye on him constantly, so he was probably one of the most carefully guarded prisoners in all of France. That obviously did not stop him from breaking free in 2007 during the Bastille Day celebrations, when four masked men picked him up in a helicopter they hijacked earlier.

Police managed to apprehend him once again, this time near Barcelona. He was transferred to a secret location—where he remains to this day.

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