1. The Bullied

In 1901, the well liked Chinese immigrant Lum You was convicted of murdering Oscar Bloom in the Pacific Northwest Territory after You had endured a beating from the known bully during a card game after which Bloom also robbed him. You had previously been threatened by a fellow immigrant and had reported it to the police. They told him to handle it himself and he responded by attacking the man with an axe but didn’t kill him. However, in the case of Bloom, You immediately went to retrieve his pistol after the beating and returned to the site of the card game, shooting Bloom in the stomach on the spot.

You was arrested for the killing and sentenced to death by hanging which was a surprise to the jurors who convicted him who had apparently expected a certain amount of leniency given the circumstances. The women of the community responded by taking 100 names down on a petition requesting You be granted clemency. This petition was possibly faked since the organizers hadn’t gotten it authenticated but was, at the least, poorly executed.

However, You had other supporters, namely those in County government. County officials apparently began leaving You’s cell unlocked every night in an attempt to get him to escape. Eventually he did although he was recaptured just a couple of weeks later and executed 24 days after that

At the gallows he told the executioner “kill me good.” This story is very sad, especially when You seemed to have been arrested for doing precisely what he’d been told, handling it himself in frontier fashion.

2. The Bastards

I don’t think anyone ever rooted for these guys and for good reason. Occurring in 2000, the escape of the Texas 7 from Kansas’s John B. Connally Unit has been compared to the legendary Alcatraz escape in 1962 because of how well planned it was. Waiting until there were as few others around as possible, the prisoners lured and captured nine maintenance officers, four correctional officers, and three other inmates not involved in the escape. They stole the maintenance worker and correctional officer clothes and then took over one of the guard towers where they stole money, guns, and ammunition before driving a maintenance truck out of the prison’s back entrance.

Unlike Mr. Yoo, above, all seven of the Texas 7 were men with violent pasts. 30-year-old George Rivas, the ringleader of the group, was serving 18 consecutive 15-life sentences for “13 counts of aggravated kidnapping with a deadly weapon, 4 counts of aggravated robbery with a deadly weapon, and one count of burglary of a habitation.” As a result, a nationwide manhunt ensued that lasted more than a month. During that time, the group robbed two stores and murdered a police officer.

Once located in Colorado, five of the men were found to have been living in an RV Park and posing as missionaries, even going so far as to attend a local church. While four of the five were arrested the final escapee took his own life rather than be arrested. The final two members of the group were tracked down at a Holiday Inn in Colorado Springs where they turned themselves over.

Four of the remaining escapees have since been executed and the remainder are on death row.

3. The Escape Artist

In 1933, Yoshie Shiratori was arrested for robbery. While awaiting sentencing in a Japanese prison he picked his handcuffs with a length of wire and escaped. Upon recaptured, he was sentenced to life in prison. This sentence didn’t agree with Mr. Shiratori either and he subsequently escaped again this time using an air vent in the ceiling to slip away. Once again, Yoshie was caught and rearrested. This time the Japanese court saw fit to add three years to his life sentence perhaps in the misguided notion that this would make any difference. Only a few years after he began this life plus three sentence, in 1944, Yoshie used his miso soup to eventually rust away his handcuffs and a piece of his cell door and escaped once again.

Japanese authorities had had enough. Upon being recaptured for a third time he was sentenced to death but what did he do? That’s right, in 1947 he escaped by using a piece of sheet metal to cut through his cell’s floorboards and used a bowl to dig his way out.

In 1948, allegedly tired of running, Yoshie turned himself in to police while asking an officer for a cigarette. His death sentence was commuted and he served 13 years willingly before he was paroled.

Yoshie remains a folk hero in Japan.

4. The Unabashed Thief

The man who came to be known as Moondyne Joe was originally kicked out of Britain and “repatriated” to Australia for petty theft of food in 1853. After showing himself to be well behaved he was given leave from his sentence and moved out into the wilderness making money by recapturing stock animals for reward and putting up fences for pay. However, one day he apparently came across a lovely horse he couldn’t resist having for himself and branded it with his own brand. Since this wasn’t his horse he was arrested and thus began Joe’s true legend on the Australian continent.

Joe was arrested by police and charged with horse theft which carried with it a comparatively huge penalty he was unwilling to pay. After nightfall, Joe escaped from the jail where he was being held and stole the magistrate’s new saddle and bridle, riding the horse into the countryside. Once law enforcement found him he’d cut the brand he’d made off the horse and killed it thus destroying any formal evidence he’d stolen the horse in the first place.

He was later arrested for allegedly stealing a steer and was sentenced to ten years of hard labor. Dissatisfied with this sentence he escaped the labor camp on foot with a partner and went on a robbery spree over the course of a month. Finally recaptured by an aboriginal tracker, Joe petitioned authorities to cut his sentence down which they granted.

Never satisfied, Joe proceeded to escape again along with three other prisoners. He and the others began an arduous trek across the Australian wilderness but they used a well known trail and, predictably, were caught again after traveling about 70 miles. Joe was given more time for having been in possession of a gun plus all the additional robberies he’d committed to supply himself for the long trip.

Not wanting him to escape again, his new cell required him to be chained by the neck to the cell bars and the cell was reinforced. The judge who sentenced him at the time confidently told him that “If you get out again, I’ll forgive you.” However, once he was allowed to do hard labor outside again he managed to break through the walls of the prison with a sledgehammer and remained free for nearly a year.

Finally, after being recaptured and serving three years in prison, the authorities learned the judge had previously promised him that if he escaped his crimes would be forgiven. In 1871, Joe was freed from prison because, authorities said, to keep him wouldn’t be fair.

5. The Bank Robber

In 1997, Pascal Payet participated in the armed robbery of a Bank of France armored car during which a police officer was killed. Payet was sentenced to 30 years in prison but escaped in 2001 with four others using a helicopter to get away. Payet was recaptured but in 2003 again escaped prison with others using a helicopter. While being hunted, the men posed as biathalon athletes who were training and apparently ran every day to keep up the guise. In case you’re confused, let’s be clear, Payet escaped from the same prison twice using the exact same means both times, a helicopter.

In 2005, Payet was charged with murder for the death of the police officer in 1997 and thirteen additional years were added to his sentence for his previous escapes. Despite being moved from prison to prison regularly to prevent another escape, in 2007 four masked men hijacked a helicopter, flew it to the prison where Payet was being held, freed Payet, and flew to the Mediterranean coast. He was recaptured a month later in Spain and has been held at an undisclosed French prison since that time presumably to prevent another helicopter escape.

6. The Con Artist

The irony of con artist Steven Jay Russell’s criminal life is that the very thing that allowed him to repeatedly escape prison is also what cause him to be there in the first place, lying.

Russell was first sentenced to prison for fraud in Texas in 1992 after he faked a slip and fall injury and sued his employer. He was found guilty of fraud and was sentenced to six months. Wearing a spare set of civilian clothes he somehow got a hold of and carrying a walkie talkie, Russell was able to simply walk out of the prison. He was arrested three weeks later and served his sentence.

The second time Russell was arrested he had managed to become the Chief Financial Officer of a medical services company where he’d immediately begun embezzling funds, $800,000 in total. He was discovered, arrested and held on $950,000 bond. Thinking outside the box, Russell called the County Records Office and told them he was the judge and had them lower the bond to $45,000 which he then paid. He was found and arrested a week later.

Sentenced to 45 years for embezzlement, Russell began collecting green highlighters once in prison and made a dye so that his uniform would look like a doctor’s scrubs. Wearing this new dyed uniform he walked right out of the prison. He was later caught while gambling in Biloxi, Mississippi.

After being returned to prison he was given an additional 45 years for escaping bringing his total sentencing to 90 years. But Russell wasn’t done. Typing up fake medical records for himself and using laxatives to fake symptoms, Russell convinced prison officials that he was dying of AIDS. He then asked for a “special-needs” parole so that he could leave the prison and die in a nursing home. At the same time, he made phone calls to the parole board and prison posing as a doctor offering experimental AIDS treatment. He was granted parole and once he was out of the prison he sent back a faked death certificate for himself.

Russell was finally caught in 1998 and is serving a total of 144 years in prison. That’s a lot of years for a non-violent crime especially when Russell could have simply disappeared if he hadn’t been willing to hang around to try and be with the man he loved who was still in prison in Texas.

Russell’s story was turned into a move entitled “I Love You Philip Morris.” 

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