In 1986, a French woman studied for months so she could learn how to fly a helicopter. Then she rented one, flew it over a prison and grabbed her husband, a convicted bank robber, from the prison’s roof.
In Australia, a man escaped prison so many times that a special maximum security prison was built for him. After it, the Governor made a promise to him “If you get out again, I’ll forgive you”. And of course he escaped again, and the Governor kept his word and set him free.
In 2014, an Arizona man escaped prison to meet with his girlfriend on Valentine’s Day. The man crawled past razor wire, scaled two fences and made his way to a bar about 10 miles away.
Two brothers from a set of triplets fooled a Russian prison when one brother swapped places with the other to give him a brief taste of freedom. Rather than returning, the freed brother ran off with his brother’s girlfriend. It took years for the authorities to realize they had been duped.
In order to escape arrest, a man feigned a heart attack. After being placed under a security watch in a hospital, he impersonated an FBI agent on the phone and told his guards he could be released.
A man escaped from a German prison by hiding in a cardboard box, which was then taken outside of the prison by courier.
In 1973 a helicopter landed in Dublin’s Mountjoy prison exercise yard, the guards assumed it was a surprise inspection until three IRA prisoners got in and escaped as a guard, who realized a Jailbreak was happening in front of his eyes, shouted, ‘Close the gates!’
A French convict used oranges painted like grenades to escape prison via a helicopter piloted by his wife who took flight lessons solely for the escape.
In 2013 a Swedish man broke out of prison one day before his release in order to see a dentist.
Steven Jay Russell impersonated a prison guard to simply walk out of prison. Upon recapture Russell lowered and paid his bail by pretending to be a judge, escaped his next capture by impersonating a doctor, and did so AGAIN by faking his death, eventually landing him a 144yr sentence.
Mike Kurtz, an American burglar, found out that eating common soap could produce the effect of ill health. His sudden and unexplainable weight loss and other symptoms baffled the prison doctors and he was able to fool officials that he was dying and received a pardon.