5 Clever Convicts Who Flew the Coop

While we would never condone breaking out of the joint, we can't help but be impressed with these folks, who did so using brains (and dental floss) over brawn.

1. FedEx-Con

While in jail, accused murderer Jean-Pierre Treiber worked in the prison's stationery manufacturing department. In September 2009, Treiber constructed a cardboard box like he did many times during his shift. But instead of filling it with paper and pens, he crawled inside himself. Sitting among the other boxes to be delivered to a nearby store, his box was loaded onto the truck without hesitation. Once on the road, Treiber cut through the tarp covering the truck bed and hopped out, disappearing into familiar the countryside where he had worked as a forestry warden before his imprisonment. Thanks to fellow inmates covering for him, prison guards didn't notice Treiber was missing for nearly seven hours, giving him a head start on the massive manhunt that followed. While out of prison, he repeatedly contacted a French political magazine by mail to proclaim his innocence, saying he broke out because he was frustrated with French law. No amount of publicity, though, could keep the police from pursuing him, and he was eventually captured three months later near Paris.

2. Once, Twice, Three Times a Chopper...

According to one of the coolest Wikipedia pages ever—List of Helicopter Prison Escapes—the first guy to use a chopper to break out of prison was Joel David Kaplan in 1971. Kaplan might have been the innovator, but Pascal Payet took the idea to a whole new level.

3. Do They Get Netflix in Prison?

How do you conceal these excavation projects from the watchful eyes of New Jersey County prison guards? You take a cue from Hollywood—The Shawshank Redemption, to be exact—and cover your escape plan with photos of pin-up girls in bikinis. But unlike Andy and Red, these escapees did not live happily ever after. Both were captured just a few weeks later and sent back to prison. Believe it or not, but they pleaded Not Guilty to escape charges.

4. 4 out of 5 Escapees Recommend It

Dental floss is pretty tough stuff. So tough, it's been used in some surprising ways for clever jailbreakers to gain their freedom.

One such fellow was Scott Brimble, who, in 2002, was serving a 64-day sentence in a Washington jail for not properly registering as a sex offender. He complained of being claustrophobic, so was given more time in the exercise yard. However, he used this time wisely by slowly sawing away at a fence using dental floss and toothpaste, which acted as an abrasive. Soon he had cut through enough of the fence he was able to pry it open and escape.

Another guy, Robert Shepard, convicted of manslaughter and armed robbery, traded cigarettes to other inmates for as much dental floss as he could get his hands on. He wove the floss into an 18-foot long rope about the thickness of a telephone cord and used it to climb over a wall. As a result, the state of Maine quickly prohibited the sale of all dental floss inside prisons, inspiring one jailbird to sue for "stress and anxiety over the inability to fight tooth decay."

5. "I Wanna Be A Toys 'R' Us Crook!"

Jeffrey Manchester was sent to jail for drilling through the roof of fast-food restaurants and then, after closing time, dropping in to rob the safe. Then he broke out of prison in June 2004 by hiding in the undercarriage of a delivery truck, concealing himself with a piece of cardboard held in place by magnets that attached to the truck's frame. But it was after he escaped that his true ingenuity shined through.

While on the lam, Manchester chose a most unusual hiding place—a Toys 'R' Us store in a strip mall. Every night for months, he'd tuck himself into a cubbyhole behind the bicycle display until the store closed. Then he'd steal baby food off the shelves for dinner and ride the bikes around the store for exercise. The next morning, he'd walk right out as though he were any other customer, but always returned each evening.

Soon after the move, Manchester decided to rob the Toys 'R' Us safe. He took a video baby monitor off the Toys 'R' Us shelf and set it up inside the store, so he could watch the nightly closing routine from the comfort of his apartment. He had planned to isolate the staff, clear out the safe, and make his escape through the secret door. That night, though, two employees slipped out the back and called police. A chase ensued and Manchester panicked, leaving through his escape hatch where police found his empty hide-out. Thanks to a fingerprint he'd left on a paint can, police were able to identify him and the manhunt began.

His picture was recognized by officials at a local church who called him "John"—a new congregation member known for giving toys to kids. "John" was dating a fellow church member who had no clue she was seeing an escaped convict. A sting operation used his new girlfriend as bait, and Manchester was re-arrested without a struggle when he showed up for her 40th birthday party.

Bonus: Sometimes It's Just This Easy

Finally, this prison escape doesn't involve any special tools, advanced planning, or even opposable thumbs (or a prison). Here's a panda in a zoo making its escape by getting a boost from a friend. As for the booster: Better luck next time, pal!