Escaping from prison isn’t as easy as portrayed in the movies. It requires thorough planning, precision, and luck. Most inmates don’t even consider escaping a possibility. However, throughout history, there have been a few masterminds who have orchestrated remarkable prison breaks. Some dug tunnels through the walls, while others utilized flaws in their cell designs. Here are the seven most notorious prison breaks of all time.
1. The Killick Helicopter Prison Break
In 1999, John Killick’s girlfriend, Lucy Dudko, hijacked a helicopter and ordered the pilot at gunpoint to fly to Silverwater Prison. They hovered over the exercise yard, giving John enough time to jump on the helicopter. Correctional officers tried to stop this escape by firing at the helicopter, but the three managed to escape.
Killick and Lucy spent one and a half months on the run until they were caught and re-sentenced. This time, Lucy was slapped with a seven-year sentence for her role in the prison break. While incarcerated, Lucy and Killick wrote more than 4500 love letters to each other.
2. Escape from Alcatraz in 1962
Back in the day, Alcatraz was the world’s toughest and most secure prison. However, that did not stop Frank Morris and the Anglin brothers from escaping. On June 12, 1962, guards woke up to find the beds of these three with dummy heads made of plaster and real hair.
Before this audacious attempt, the three had been placed in adjoining cells, contributing significantly to their escape. The trio exited the cells via the air vents, which led to a workshop. Considering Alcatraz was situated on an island, Frank and the Anglin brothers had stolen 50 raincoats, which they used to make a raft.
Details of their escape were leaked by another inmate, Allen West, who was part of the plan but got left behind. This prison escape is so interesting because no one knows what happened to these three inmates. There are theories that they may have drowned in their raft. Others claim they made it out alive, and the Anglin brothers might have attended their mother’s funeral in disguise.
3. Frank Abagnale Conned His Way Out of Prison
Frank Abagnale was a renowned con artist who was arrested multiple times in different countries; he inspired the film “Catch Me If You Can.” His most notable scam was how he conned his way out of the Federal Detention Center in Atlanta – he impersonated a prison inspector after being sentenced to twelve years in incarceration in 1971.
With the help of his friend Jean Sebring, she faked a prison inspector’s card and an FBI agent badge, which she had given him while visiting. With these documents, Frank Abagnale convinced the guards that he was a prison inspector. Using his charm, Frank walked out of prison without a scratch on his back. He showed the guards his ID and insisted on talking to an FBI agent, his friend Jean Sebring. Abagnale was arrested again in 1974.
4. Redoine Faid’s Two Crazy Prison Escapes in 8 Years
Redoine Faid is an infamous armed robber in France. His first prison break was in 2010, when he blasted his way out using explosives that were hidden in tissues. Before his escape, Redoine Faid held four guards hostage, blew the walls, and escaped in a getaway car that was found incinerated.
Eight years later, Redoine Faid was arrested but escaped again. This time around, he used John Killick’s approach. A group of masked thugs hijacked a helicopter, flew it into Reau Prison, and landed it in the yard.
They released smoke canisters to conceal their identities from the prison cameras and then broke through prison doors and left with Redoine Faid. This made it one of the most dramatic prison escapes in France.
It is believed that the men had obtained intel by flying drones above the prison a few months prior to the escape. Redoine Faid was caught later on and is serving a 14-year prison sentence.
5. El Chapo’s Second Prison Break
The first time El Chapo escaped from prison in 2001, it wasn’t as dramatic because he hid in a laundry cart and was ferried out of the facility. At a time when corruption was so rampant in Mexico, this was a walk in the park for Guzman.
However, in 2015, he orchestrated one of the smartest prison breaks that even got documented into a Netflix series. While being held at the Altiplano Maximum Security Prison, El Chapo organized for a 1.6km tunnel to be dug beneath the facility. When it was ready, all he had to do was get below ground and ride a motorcycle through the man-made hole. He was arrested later and is now serving life imprisonment at the ADX Florence in Colorado.
6. The Octopus Escape
When building prison cells, the space for the food slot is designed to be so small that nothing else can fit through. That’s not the case for the Korean Houdini, Choi Gap-bok. In 2012, this yogi covered his body in lotion, neatly arranged pillows to appear like he was still sleeping in his cell, and slipped out through the food slot space.
According to CCTV footage of his escape, Choi was as flexible as an Octopus. After passing through the food slot, he slipped out of a narrow window and went missing for six days before being caught. This was not the first time Choi had pulled such a move. A few years before, Choi escaped through a prison bus’s bars.
7. John Dillinger’s Two-Time Prison Escapes in a Year
John Dillinger was an infamous bank robber and murderer who escaped from prison twice in just one year. In 1933, John Dillinger and eight other inmates smuggled rifles and shotguns into their cells, which they used to force their way out of prison. Two guards were shot during the escape.
Instead of “laying low” as most escapees would, John Dillinger continued making more robberies and was arrested again in January 1934. Because of his track record, he was placed in an escape-proof cell at the Lake County Jail.
Two months later, John Dillinger made a wooden gun, which he used to trick the prison guards who let him out. He then got a hold of two machine guns, which he used to escape Lake County Jail. He was shot and killed by FBI agents in the same year.