5 Craziest Prison Breaks in History

Prison facilities make our society safer from people that need to be locked up. But in rare cases, cunning prisoners use their skills and talent to escape. However, Jail officers work hard around the clock to prevent these escapes. We have gathered a list of 5 craziest prison escapes of all time.

1. Alcatraz Raincoat Raft Escape

Image source: https://www.brain-sharper.com/entertainment/alcatraz-story-ob/

Situated on a remote island in the middle of San Fransisco Bay, Alcatraz is one of the most unimaginable prisons in the world to escape. It housed some of the US most wanted criminals including MGK, Al Capone and etc.

Throughout its history,  there are approximately 1,545 men did time at the maximum-security facility, nicknamed The Rock, and there were 14 different escape attempts involving 36 inmates. 

But the craziest attempt took place in June 1962, when three prisoners fled the island on a raft from raincoats. Months before their daring escape, they had used homemade tools to secretly widen the ventilation holes in the walls of their cells, which they crawled their way out of freedom.

In their beds, they left lifelike dummy heads they’d devised as decoys. The San Fransisco Mayor conducted a large-scale manhunt, but the fugitives never were heard from again. They are believed to be likely drowned in the San Francisco Bay’s strong, cold currents or eaten by the sharks, but who knows?

Clint Eastwood starred in a 1979 movie that was inspired by the prison break entitled “Escape from Alcatraz.”

2. Britain’s Biggest Prison Break

On September 25, 1983, 38 inmates, all of them were members of the Irish Republican Army, broke out of Her Majesty’s Prison Maze near Belfast, Northern Ireland.  It is the biggest prison break in Britain’s history.

Image source: https://www.irishnews.com/news/northernirelandnews/2021/04/09/news/jim-jaz-mccann-book-reveals-how-pictures-taken-by-ira-prisoners-of-the-1983-maze-escape-never-saw-the-light-of-day-2281855/

It is a maximum-security facility mostly for men convicted of crimes linked to the conflict between unionists who wanted Northern Ireland to remain part of the United Kingdom and republicans who favored the unification of Ireland. 

In 1981, a group of Irish republicans at Maze Prison launched a hunger strike; 10 died, including their leader, Bobby Sands. 

Image source: https://www.irishnews.com/news/northernirelandnews/2021/04/09/news/jim-jaz-mccann-book-reveals-how-pictures-taken-by-ira-prisoners-of-the-1983-maze-escape-never-saw-the-light-of-day-2281855/

The 1983 escape occurred after inmates, armed with smuggled guns and knives, overpowered guards and hijacked a truck delivering food to the prison. Prison officers tried to block the vehicle from getting past the gate, forcing the escapees to jump from the back of the vehicle and run. One guard was stabbed during the escape and died of a heart attack, while nearly two dozen other prison officers were injured. Within a few days, 19 of the men were caught (three others never made it off the prison grounds) but the others got away. Several of the men eventually made it to the United States. The Maze prison was closed in 2000 as part of the 1998 Good Friday peace accord.

3. El Chapo Escapade

From 2014 to 2018 Joaquin “El Chapo” (“Shorty”) Guzman was one of the world’s most-wanted criminals during that time.  He was arrested after more than a decade of hiding later on and was jailed in the US. But before that, let’s take a look a little bit at his violent history.

Image source: https://slate.com/news-and-politics/2016/11/could-joaquin-el-chapo-guzman-pull-off-another-audacious-escape.html

Joaquin in his schooldays was first arrested in 1993 and sentenced to 20 years behind bars for murder. However, while serving his sentence in a high-security prison in the Mexican state of Jalisco, he bribed jail officers and continued to run his criminal organization.

Then in 2001, he easily escaped. Guzman was wheeled out in a laundry cart, while other sources suggest prison officials simply let him walk out.

Image source: https://www.businessinsider.com/el-chapo-guzman-escape-route-mexican-prison-2016-7

Being free from jail, his drug cartel further expanded. He used violence, bribery, and a large network of informants to help him off the radar while being head of the Sinaloa Cartel, the biggest cartel in the world. Then it grew into the largest supplier of illegal narcotics to America, and the U.S. government offered a $5 million reward for information leading to his arrest.

On February 22, 2014, the combined forces of DEA and Mexican Police finally tracked down the drug kingpin to an apartment in Mazatlán, Mexico, and arrested him. However, on July 11, 2015, Guzman, then incarcerated at the nation’s highest-security penitentiary, Altiplano, approximately 55 miles west of Mexico City, once again escaped this time via a hole in the floor of his cell and out through a mile-long tunnel that had been secretly dug and equipped with lights and ventilation. Guzman was re-captured by Mexican authorities in 2016.

4. Ted Bundy Escapade

Image source: https://abcnews.go.com/US/notorious-serial-killer-ted-bundy-escape-custody/story?id=61032623

In 1976, Ted Bundy was arrested and served his time in Utah prison for a kidnapping conviction. The next year, he was moved to Aspen, Colorado, for a murder trial. During his break at a courthouse hearing in June 1977, Bundy, who was acting as his own attorney, requested to use the court’s law library. Being alone, he took advantage of it and jumped out of a second-floor window then fled up Aspen Mountain.

During the six days, of hiding, Bundy got lost, stole a car, and returned to Aspen, where he was caught by police. He was returned to the county jail in Glenwood Springs, 40 miles away. I

Then in December of the same year, he escaped again. After months of losing weight Bundy was able to squeeze his way out through a hole made for a light fixture in the ceiling of his cell, and drop down into a jail keeper’s apartment and walk out the front door.

From there, he made his way to Florida, where he began his killing spree. He murdered two female Florida State University students and a 12-year-old girl. Bundy was apprehended by police in Pensacola on February 15, 1978. Before he was put to death in the electric chair in 1989 at age 42, Bundy confessed to 30 murders around the U.S.; some experts have suggested the actual number might be higher.

5. Fake Gun Escape

Image source: https://www.indystar.com/picture-gallery/life/2015/03/05/new-john-dillinger-museum-opens-on-anniversary-of-crown-point-escape/24447045/

After being jailed in his 20s for attempting to hold up a small-town Indiana grocer, the famous gangster John Dillinger was paroled in May 1933. Then he went on to pull off various bank robberies that turned him into one of America’s most-wanted gangsters.

But in September 1933, after years of hiding, he was arrested in connection with a bank heist and jailed in Lima, Ohio. The following month, several of Dillinger’s criminal associates showed up at the Lima jail and posed as law enforcement officials, informing the sheriff they wanted to see Dillinger.

When the sheriff asked to look at the men’s badges, they killed him then sprung Dillinger from his cell. In January 1934, while Dillinger and some accomplices were holding up a bank in East Chicago, Indiana, a police officer was shot and killed. Dillinger was apprehended later that month in Tucson, Arizona. 

Afterward, he was extradited to Indiana to stand trial for the East Chicago murder and held at the county jail in Crown Point, a facility authorities had bragged was escape-proof. However, on March 3, 1934, Dillinger, armed with a fake gun (either smuggled in by his attorney or made by Dillinger himself), forced guards to release him, stole a sheriff’s car and escaped. That July, FBI agents finally caught up with the 31-year-old gangster and shot him dead as he was leaving a movie theater in Chicago.

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