That was July of 1724. Two months later, Sheppard was captured for the third time and once more found himself in Newgate. This time, the authorities were determined not to let him escape. He was allowed no visitors. After a whole kit of escape tools was found hidden in his cell, he was moved to a special room known as The Castle. This room was windowless, in the middle of the prison, and with a securely locked double door. There was no furniture, nothing but a single blanket. Sheppard’s wrists were manacled, and his ankles chained, with the ankle chain slipped through an iron bolt imbedded in the floor.
Sheppard, at this time, was twenty-three years of age. He was short, weak, sickly, suffering from both a venereal disease and too steady a diet of alcohol. His physical condition, plus the manacles and the placement of his cell, seemed to make escape absolutely impossible.
Sheppard waited until October 14th, when the opening of Sessions Court was guaranteed to keep the prison staff too busy to be thinking about a prisoner as securely confined as himself. On that morning, he made his move.
First, he grasped in his teeth the chain linking the wrist manacles, squeezed and folded his hands to make them as small as possible, and finally succeeded in slipping them through the cuffs, removing some skin in the process. He then grabbed the ankle chain and with a single twisting jerk, managed to break the link holding him to the bolt in the floor.
He now had a tool, the one broken link. Wrapping the ankle chains around his legs, to get them out of the way, he used the broken link to attack one wall, where a former fireplace had obviously been sealed up. He broke through to the fireplace, only to discover an iron bar, a yard long and an inch square, bisecting the flue a few feet up, making a space too small for him to slip by.
Undaunted, he made a second hole in the wall, at the point where he estimated the bar to be, found it and freed it, and now had two tools as well as an escape hatch. He crawled up the flue to the floor above, broke through another wall, and emerged in an empty cell. Finding a rusty nail on the floor — for tool number three — he picked the door lock with it, and found himself in a corridor. At the end of the corridor he came to a door bolted and hinged on the other side. He made a small hole in the wall beside the door, reached through and released the lock.
The third door, leading to the prisoners’ pen in the chapel, he popped open with the iron bar. The fourth door got the same treatment, and now he came to a flight of stairs leading upward. He knew his only chance for escape lay in reaching the roof.
At the head of the stairs was door number five. Thinking it was the last, Sheppard and his iron bar tore through it almost without stopping. And ahead of him was door number six.
This sixth door was fastened with a foot-wide iron-plated bar, attached to door and frame by thick iron hoops, plus a large iron bolt lock, plus a padlock, and the whole affair was crisscrossed with iron bars bolted to the oak on either side of the door.
Sheppard had now been four hours in the escape. He was exhausted, his hands were bleeding, the weight of the leg shackles was draining his energy, and the door in front of him was obviously impassable. Nevertheless, Sheppard went to work on it, succeeding at first only in bending the iron bar he was using for a tool.
It took him two hours, but he finally managed to rip the crossed bars down and snap the bolt lock, making it possible to remove the main bar, and he stepped onto the prison roof.
So far, the escape had taken six hours. It was now almost sundown. Sheppard crossed the roof and saw the roof of a private house next door, twenty feet below him. He was afraid to risk the jump, not wanting to get this far only to lie down there with a broken ankle and wait for the prison officials to come drag him back. So, regretfully, he turned around, recrossed the roof, went down the stairs and through the chapel, back down the corridor and into the cell above The Castle, down the fireplace flue and back into his cell, which was ankle deep in stone and plaster from the crumbled wall. He picked up his blanket, retraced his steps again, and went back to the roof. He had forgotten tool number four, and so he had simply gone back for it!
Atop the prison again, Sheppard ripped the blanket into strips, made a rope ladder, and lowered himself to the roof of the house next door. He waited there until he was sure the occupants had gone to sleep for the night, then he crept down through the house and out to freedom.
In the normal manner of escapees, however, Sheppard could never learn to devote as much energy to staying out as to getting out. He spent the first four days hidden in a cowshed, until finally someone came along who would bring him a hacksaw and help him shed the ankle chains. He then went straight home, where he and his mother celebrated his escape by getting drunk together on brandy. They were still drunk when the authorities showed up, and this time Sheppard stayed in Newgate long enough to meet the hangman.
Here is the core of the problem. The tougher the prison officials made their prison — the more they challenged Sheppard and told him that this time he couldn’t escape — the more determined and daring and ingenious Sheppard became.
This misdirected genius was never more evident than in the ten-man escape from Walla Walla State Penitentiary in Washington State in 1955. Their escape route was a tunnel under the main wall, but one tunnel wasn’t enough for them. They also had tunnel routes between their cells, so they could communicate and pass materials and information back and forth. When they were recaptured — which, in the traditional manner, didn’t take very long at all — the full extent of their ingenuity and daring was discovered. Each of the ten carried a brief case containing a forged draft card, business cards, a driver’s license, birth certificate and even credit cards and charge-account cards for stores in Seattle. Beyond all this, they all carried identification cards claiming them as officials of the Washington State prison system, and letters of recommendation from state officials, including the warden of Walla Walla State Penitentiary. And four of the escapees carried forged state pay checks, in amounts totaling over a thousand dollars. Every bit of the work involved had been done in the prison shops.
Compare this with the record of a jail such as the so-called “model prison” at Chino, California. Escaping from Chino is almost incredibly easy. There is a fence, but no wall, and the fence would be no barrier to a man intent on getting away. The guards are few, the locks fewer, much of the prisoners’ work is done outdoors, and the surrounding area is mostly wooded hills. For a man determined to escape, Chino would offer no challenge at all.
And yet, Chino has had practically no escapes at all!
Perhaps the lack of challenge is itself the reason why there are so few escapes from Chino. The cage in which the prisoner must live is not an obvious cage at Chino. He is restricted, but the restrictions are subtle, and he is not surrounded by stone and iron reminders of his shackled condition. At tougher, more security-conscious prisons, the challenge is flung in the convict’s face. “You cannot escape from here!” Inevitably there are those who accept the challenge.
The challenge at Chino — and at other prisons constructed from much the same philosophy — is far different “You should not escape from here! And when you know why society demands that you stay here, you won’t need to escape. You will be released.”