7 People Who Broke Into Prison

Whether you believe prison exists as a deterrent, a place for penitence, or an avenue to recalibrate a broken moral compass, most everyone would agree on one thing: it stinks. Inmates count the years, days, and hours until their release; a social faux pas can result in getting the business end of a sharpened toothbrush in your ear.

Occasionally, though, some on the outside feel compelled to scramble over the walls and get a taste of incarcerated life. Here are seven who decided to defy convention and voluntarily leave freedom behind.

1. Sylvester Jiles

Spend enough time behind bars and you’re likely to become what some refer to as “institutionalized,” unable to cope with life as a free man. That may have been the case for Florida inmate Sylvester Jiles, who was sentenced on a manslaughter charge and released in late 2009. Jiles spent only three days breathing fresh air before he was literally begging guards to let him back in, according to NBC Miami. When the confused correctional officers sent him away, Jiles—who reportedly feared for his life on the street—tried scaling the wall but got caught in barbed wire. (This, naturally, is the purpose of barbed wire.) Fortunately for Jiles, such behavior was considered violation of his probation, and he was sentenced to another 15 years.  

2. Monique Armstrong

If you're going to attempt a break-in, it’s probably best not to phone the police in advance. But that was exactly what Monique Armstrong did shortly before she was able to breach the perimeter of a Colorado facility holding her 18-year-old brother on drug charges. According to the New York Daily News, in April 2014, Armstrong cleared the chain-link fence and tried smashing the windows of a building that did not happen to be housing him, then asked to be arrested—which she was, on criminal trespass and criminal mischief charges, seemingly unaware her brother was due to be released on bond just a few hours later.

3. A Thief

A women’s prison in Windward Oahu is apparently an attractive site for breaking and entering: one unidentified thief cut through a fence in January 2015 and swiped tools from a work shed on the property—and it wasn't the first time such an event had occurred. At least one other unidentified person had broken into the area before. After the story was publicized, nearby citizens expressed some concern the same route could be used for inmates going in the opposite direction. Officials assured them that prisoners “typically” didn’t use that area.

4. Tiffany Hurd

The Butler County Jail in Ohio does not appear to offer any exceptional accommodations, but that didn’t stop Tiffany Hurd from reportedly trying to navigate a razor-wire fence in an attempted break-in during the summer of 2012. According to the New York Daily News, Hurd told officers she wanted to be arrested and was slapped with a misdemeanor disorderly conduct charge. She was said to be intoxicated at the time of the incident.

5. Serhiy Vlasenko

Life behind bars has not been good to Yulia Tymoshenko, the former Ukrainian Prime Minister who was convicted in 2011 of embezzlement. Hearing she was being denied proper health care, her lawyer, Serhiy Vlasenko, grew agitated when he went to visit her in April 2012 and could not find a guard to admit him entry. So, according to Radio Free Europe, Vlasenko crawled under a fence and confronted the warden on prison grounds.

Tymoshenko was later released in 2014, said to be the victim of a politically motivated conviction. Adding to the soap opera, Vlasenko himself wound up in legal trouble stemming from a divorce and accusations of car theft, which pundits also attributed to a smear campaign.

6. Martin Ussery

Aside from the rare Johnny Cash concert, California’s Folsom Prison has precious little to recommend it. Why, then, would former inmate Marvin Ussery want to return? According to Digital Journal, Ussery, who was paroled in 2008 following a sentence for robbery, was found hiding in tall grass on the prison's grounds in August 2011, hours after thermal imaging technology spotted him scaling a fence. Ussery claimed he was “reminiscing” about his stay there; officials suspected he was not so much nostalgic as eager to smuggle contraband on the property for profit. (Ussery needed all the cash he could get: His bail for the charge of breaking into the prison was set at $1 million.)

7. Incarcerated Inmates

The Berrimah jail in Australia may need to reconsider its security standards. According to the Australian Broadcasting Company, in July 2014, it was discovered that several detainees had been slipping out of the unit to go out drinking and then return before a count was taken in the morning. Their sabbatical was discovered when several of the men were arguing over a cell phone they had brought back with them. At the time of the incident, authorities told media that they were still trying to figure out whether an inmate returning still constituted an escape.