The fifth? He was the exception. It took the authorities nearly twenty years to find him, and when they did, they discovered he had become the mayor of a small town in Canada. His record since his escape from Leavenworth was spotless, and so he was left to live out his new life in peace.
The courage and daring, the ingenuity and imagination, the skill and talent demonstrated in these and similar escapes, if used in the interests of society rather than directed against society, would undoubtedly make such men as these among society’s most valuable citizens. But the challenge is given these men, and they accept that challenge. They are not challenged to use their talents to benefit society, but to outwit society.
In fact, there seems to be a correlation between rigidity of control and attempts to escape. The tighter the control, the stronger and more secure and solid the prison, the more escape plans there will be, the more attempted escapes, and the more successful escapes.
The career of Jack Sheppard, probably the most famous despoiler of “escape-proof” prisons of all time, is a clear-cut demonstration of this. In one five-month period in 1724, Sheppard escaped from Newgate, England’s “impregnable” prison, no less than three times! The first time, he had help from inside the prison, which is probably the easiest and most common type of jailbreak. The second time, he had tools and assistance from outside, a little more difficult but obviously not impossible. The third time, without tools and absolutely unaided, he successfully completed one of the most daring and complex escapes in history.
Sheppard, born in 1701 and wanted as a highwayman and murderer before he was out of his teens, was first jailed in Newgate in May of 1724. When arrested, he had been with a girl friend, Bess Lion, who was also wanted by the police. They swore they were married and so, in the manner of that perhaps freer day, they were locked together in the same cell. Bess had managed to smuggle a hacksaw in with her — history doesn’t record how — and as soon as the two were alone, they attacked the bars of the window. But it was a twenty-five-foot drop to the prison yard, and the rope ladder they made of their blankets didn’t reach far enough. So Bess removed her clothes, which were added to the ladder, and they made their way down to the yard, the nude girl first. Bess rolled her clothes into a bundle, and she and Sheppard climbed over a side gate which was no longer in use. Bess put her clothes back on, and the two of them walked away.
He was recaptured almost immediately, returned to Newgate, and this time held long enough to be tried for his crimes and sentenced to be hanged. The day before the scheduled hanging, he was brought, chained and manacled, to the visitors’ cell. His visitors were Bess Lion and another girl friend, Poll Maggott. While Bess “distracted” the guard — history is somewhat vague on this point, too — Poll and Sheppard sawed through the bars separating them, and Poll, described as a “large” woman, picked Sheppard up and carried him bodily out of the prison, since the ankle chains made it difficult for him to walk.
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.