Smooth Criminals: Most Daring Prison Breaks of All Time

What else is left to do when you’re one of the most wanted criminals in your time who got busted and jailed in the highest security prison? You would use your brainpower and escape in the craziest, most creative way with the help of your accomplices. The options are endless— from underground tunnels to transforming into a woman. Unfortunately, these three criminals did not let the most secure prisons stop them from attempting their most daring escapes.

Ronaldo Silva

After a failed attempt at escaping with the help of armed men invading the jail to break him out, drug trafficker Ronaldo Silva took his escaping game to a different level in 2012 when he decided to disguise himself as a woman. With the help of his wife, who exchanged clothing with him during one of her visits, he dolled himself up by shaving his arms and legs, even putting on lipstick, a lovely curly wig, wearing a bra and panties, and slipping into a blue dress, and wearing high heels.

According to jail director Carlos Welber,

“He was wearing a wig, painted false nails and a long dress. He’d spent a long time shaving his legs and arms. There was a lot of preparation and premeditation involved in this.”

He almost made it out of Penedo Prison in Brazil, unnoticed by the guards on post until he was spotted by one of the police officers 30 minutes after, noticing his funny walking with his feet unsteady with the heels. According to his wife, Silva asked that they exchange clothes during her visit, but she didn’t really know why her husband wanted to cross-dress and just went with it anyway. And so he was cuffed and sent back to his cell.

Maybe he should’ve just ditched the heels and gone with flats instead?

Michel Vaujour

In 1986, Michel Vaujour and his gang were caught after a failed armed robbery in France. He was sentenced to 18 long years in prison with no chance of early release for what he did. He was locked in the Le Sante prison, where he attempted four escape attempts during his first few months.

According to him, it was his wife who drove him to keep on trying to escape. The said wife was Nadine Vaujour. She would always visit her husband as often as possible, bringing him treats with small hidden notes of information that she couldn’t say aloud. One of them was her plan of how and when she would help him escape the jail. Outside, she spent her time learning how to fly a helicopter by taking flight lessons. She did this to fly the love of her life back to freedom.

It was in May 1986 when they planned to carry out the great escape. Michael “forced his way onto the prison’s roof by wielding nectarines that were painted to look like grenades,” according to CNN. We’re not sure how good the paintings on those nectarines were that the French guards believed they were real explosives.

Above, Nadine, in her helicopter, slung a rope for Michel to climb on before flying away and landing on a football field. From there, they successfully drove away, at least for a brief moment. Soon enough, Nadine and Michel were found and arrested in southwestern France. Michel was sent back to do his original sentence and earned his freedom in 2003.

El Chapo

The notorious Mexican drug lord Joaquin “El Chapo” Guzman was perhaps one of the most well-known criminals. He succeeded in escaping twice ever since he was captured in Guatemala on June 10, 1993.

His first escape attempt was in 2001. He successfully bribed his guards and escaped from his top-security prison. In 2014, he was captured in Mazatlan after hiding in tunnels for two days. After more than a year, he again escaped from his maximum-security prison via a painfully tight 20 inches tunnel hole in the shower area of his cell block and into a lit and ventilated tunnel system. Once more, he was captured in Los Mochis, Sinaloa, in January 2016 after a shootout with Mexican marines.

He was sentenced to a lifetime plus 30 years in prison and locked in the United States Penitentiary Administrative Maximum Facility, or ADX, in Florence, Colorado. No one has escaped since it opened in 1994.