Planning a successful prison break is no simple feat. It takes nerve, guile, and ingenuity. The idea of a prisoner on the run, by its very nature, is sensational and inspires films and captures Americans’ imaginations. But planning an escape and making it happen are two very different things. This a look at some of the personality traits and preconditions involved with such attempts and how criminals sometimes do manage to break out, even if only for a short, dangerous while.

The Perfect Prison Break

Guts, intestinal fortitude, balls—whatever you want to call it—executing a prison break takes boldness. Many prisoners may dream of making a run for it, but only a small percentage give it a shot. This certainly makes sense when you consider the repercussions: extending your prison sentence, injury, getting shot, or death. 

Taking the time to devise a plan and carrying it out, for even a moment of freedom, is not easy. Escape attempts can and often do go awry, and there is danger for all involved. In fact, in March of this year, an inmate in an Oklahoma county jail took a guard hostage during medication distribution. The standoff ended with police shooting and killing the prisoner.

Likewise, in July, a prisoner in Devils Lake, North Dakota, attempted an escape by scaling a fence. Instead, razor wire ripped through his skin, and he received a stay in the jail’s maximum-security area. In 1989, drug kingpin Benjamin Kramer, 34, was serving a life sentence with no parole in a Miami-area federal prison. His escape plan involved a helicopter swooping into the prison’s exercise yard and him jumping on board. 

The plan almost worked, but the chopper crashed as it attempted to take off again. Kramer sustained a broken leg, but his pilot was in even worse shape with two broken legs, fractured facial bones, and an eye injury. Ouch!

Intelligence And Ingenuity

As Tom Petty sang, “The waiting is the hardest part.” That certainly is true for life behind bars, but having time on their hands can allow savvy prisoners to plot and scheme for a chance at freedom. In 1962, Frank Morris and brothers John Anglin and Clarence Anglin had considerable time on their hands while serving their sentences at Alcatraz. The prison seemed inescapable; 14 men had tried over three decades, and all came up short—or dead.

These problem solvers, however, seemingly covered every base in seven months of preparation. They devised ​dummy heads with real hair to fool guards at bed check. They used old sawblades and homemade drills made from a broken vacuum cleaner to tunnel through air vents in their rooms. The prisoners also fashioned a rubber raft and life preservers from 50 stolen raincoats, using a concertina (similar to an accordion) to inflate them. Everything was well planned when they finally shoved off into San Francisco Bay. Did they make it? The FBI said no at the time, but their bodies were never found. 

Beyond higher-level thinking, this escape also points to a personality trait needed for an escape involving multiple people: trust. “Trust, among other cons, was a major factor in facilitating a successful escape,” says Michael Esslinger, author of Escaping Alcatraz. “Prisoners also had a lot to gain by tipping off prison staff. They could acquire special consideration for transfer or good time credits for an early release. The prisoners involved in the escape would also risk other prisoners demanding to be a part of it. The more men involved, the more risk of being caught.”

Social Skills Are Imperative to a Jail Break

The search for Richard Matt and David Sweat gripped the country in June 2015. Matt faced 25 years to life for murder, and Sweat was also locked up for life, convicted of murder as well. The two used hacksaw blades, chisels, and drill bits to tunnel through walls at the maximum-security Clinton Correctional Facility in Upstate New York. 

Beyond their ingenuity, the pair also lured a prison seamstress and a guard to help. Escape-minded prisoners have a knack for befriending workers and using them as needed, and Sweat credited his partner with this particular skill.

“Matt could ingratiate himself with people,” says Chelsia Rose Marcius, author of Wild Escape: The Prison Break from Dannemora and the Manhunt that Captured America, which details the escape and subsequent manhunt. “He did that in a pretty slick way. The two of them together made an excellent team. David is very likable, smart, and well-spoken, but he’s kind of a quiet guy. Where Matt was a little more gregarious and was the one to break the ice with people like Joyce Mitchell, who was the prison seamstress, and other people who unwittingly helped them.”

After their escape, the pair survived in the Adirondack Mountains for three weeks before being discovered by authorities. Matt didn’t have the chance to tell his story. He was shot and killed by a U.S. Border Patrol agent about 50 miles from the prison.

Prison Breaks Require Money And Power

Friends in high places or a few bucks in the bank can always be helpful in a pinch. This also applies to those attempting to get out of serving their time in the slammer, and it certainly worked for Joaquín “El Chapo” Guzmán. The drug kingpin escaped maximum-security prisons not once but twice. The first escape occurred in 2001 and involved a maintenance worker wheeling the drug lord right out the front door in a laundry cart. After outfoxing Mexican authorities for over a decade, Guzmán was captured again. 

In 2015, however, El Chapo’s henchmen built a mile-long tunnel underneath his cell. The area was supposed to have been the prison’s most secure, but Guzmán wielded plenty of power and influence among prison staff. Is a third escape in the cards? That seems unlikely. After his recapture in 2016, El Chapo was sentenced to life plus 30 years in the United States. He is serving his time at the famed “supermax” prison in Florence, Colorado. This facility is dubbed the “Alcatraz of the Rockies,” in more than 25 years of operation, no one has ever escaped. 

Cold-Blooded Violence

Sometimes, brute force can prove to be the best method of escape for some prisoners. Those already with violent dispositions who are facing lengthy prison sentences may feel that they have nothing to lose. That was the case in December of 2000 when seven prisoners escaped from a maximum-security prison in South Texas.

The “Texas Seven” faced prison terms for crimes that ranged from violent child abuse to sexual assault to aggravated robbery. One was even convicted of hiring a hitman to take out his wife. All faced decades in prison. The seven men knocked several prison personnel unconscious, tied them up, and made their escapes. These fugitives drew national attention and committed several crimes while on the run.

The hunt for the Texas Seven ramped up even more after the group murdered Aubrey Hawkins, a police officer in Irving, Texas, who had responded to a burglary the escapees were committing. This prison break was even featured on America’s Most Wanted. It didn’t end well for the Texas Seven, and six of the seven were arrested in January of 2001 in Woodland Park and Colorado Springs, Colorado. One member of the gang committed suicide before being captured, and four of the remaining six have since been executed. Two remain on death row.

Prison Breaks In Pop Culture

Movies, TV shows, and novels all romanticize the prison break, and well-publicized cases make for interesting real-life drama. But the reality can be a dangerous and, at times, deadly affair for prison guards, police, and the prisoners themselves. So, if you are in a position that has you even considering your own “Shawshank-style” getaway, things obviously haven’t turned out too well for you. 

While the best idea is to avoid that jail cell in the first place, if that is no longer an option, legal appeals or simply serving your time are likely safer, sounder avenues for being free once more. This is especially true when you consider that most prison escapees are recaptured or worse. And even if that isn’t the result, a life on the run can be a difficult life indeed.