The Mammoth Book of Prison Breaks (25 page)

It wasn’t that long before Sheppard was a guest of the roundhouse himself. His brother Tom was also a thief, and the pair had teamed up to carry out various robberies. When Tom was arrested, he tried to implicate his brother and Lyon, but they couldn’t be found. Sheppard was betrayed by another of his companions, James Sykes, who got Jack drunk and then handed him over to the police. Sheppard didn’t remain a prisoner for long; after a brief interrogation, he was sent to the roundhouse, but broke through the roof and escaped that night.

His second escape was a little trickier. Within a few days of absconding from the St Giles Roundhouse, Sheppard found himself in the one at St Ann’s, in Soho, after a pickpocketing in Leicester Fields (modern Leicester Square) went wrong. Lyon came to visit him, was recognized as his accomplice and arrested. The pair of them were sent to New Prison in Clerkenwell by the magistrates, and because they were believed to be married, they were allowed to share a room, known as the Newgate Ward (which has led to some confusion over the years; this wasn’t part of Newgate Prison.)

Sheppard and Lyon were visited by various friends over the next few days, who were able to provide them with some necessary tools. Early one morning, Sheppard filed off his chains, then made a hole in the prison wall. The Newgate Ward was on an upper storey, and was some 25 feet above the ground. Sheppard removed an iron bar and a wooden one from the window, then tied a blanket and sheet together and fixed them to one of the remaining bars. Sheppard lowered Lyon down to the ground, then climbed down the makeshift rope himself, only to find themselves still trapped in the yard, with a 22-foot-high wall in front of them. However, Sheppard was undeterred and the two of them clambered over the gate, using the locks and bolts as hand and foot holds.

Jack Sheppard continued working as a thief but he was making enemies, notably Jonathan Wild, who became annoyed when Sheppard refused to fence his stolen goods through him. Determined to curb the younger man, but unable to lay his hands on him, Wild plied Elizabeth Lyon with brandy to make her give up Sheppard’s address. This she did, and he was arrested and indicted at the Old Bailey on several charges of robbery. On 30 August 1724, he was sentenced to death and imprisoned in the old jail of Newgate to await sentence.

Newgate Jail had been rebuilt in 1672 following its destruction in the Great Fire of London six years earlier. One of the unusual features was the area around the cells holding the condemned prisoners: the inmates came down a dark passage to a hatch, which had large iron spikes preventing anyone from passing through. Once again, outside friends were able to smuggle tools in to Sheppard, and he cut through one of the spikes so that it barely remained in position. On the day that the warrant was sent for Sheppard’s execution, Lyon and Polly Maggot went to visit him. They distracted the guards as he broke through the final piece of the spike, leaving a hole wide enough that he could wiggle through. The two women quickly dressed him in a nightshirt they had brought to disguise the irons he was wearing, and hurried him out of the prison. Some of the other convicts tried to follow him, but the prison officers saw the gap in the hatch and prevented any other escapes. Sheppard headed for the waterfront at Black-Fryers-Stairs (Blackfriars), and headed upriver to the Horse Ferry at Westminster.

Sheppard realized that London was perhaps becoming too dangerous: Wild and his men would be looking for him, as would the officers of the law. He and a friend, William Page, headed up to Warnden in Northamptonshire for a few days to stay with Page’s family. However they weren’t made welcome, and within the week they had returned to London. On Friday 4 September, the day he was due to hang, Sheppard cheekily wrote a letter that was printed in
The Daily Journal,
addressed to “Jack Ketch”, the popular nickname for the hangman, saying that he was drinking a toast to his health, and wishing his friends who had hanged, a “bon repo” – a good sleep.

Jack was quite right: he should have stayed away from London, and he would have been well advised to keep out of trouble when he did return. However, old habits died hard: the day after his return from Northamptonshire, he and Page stole three watches from a shop in Fleet Street. When he tried to fence them, he was advised to lay low, and the two men headed up to Finchley, north of London. However someone informed on them to the Newgate prison turnkeys, and on 10 September they were arrested. Page surrendered immediately; Sheppard tried to make a run for it, but faced with armed prison officers, gave up, begging them not to shoot him on the spot. He was taken back to Newgate, and this time the warders were taking no chances. He was put back into a portion of the condemned hold known as the Castle, where a heavy pair of irons was wrapped around him, and he was then chained to a staple fixed in the floor.

Such trifling inconveniences weren’t going to stop Jack Sheppard from escaping from Newgate. If he could get hold of the right tools, he was convinced that he could get out of his chains and away from the prison. Unfortunately, the guards were keeping a close eye on him: every visitor was carefully watched to make sure that they didn’t try to pass him anything he could use. On one occasion when he was left on his own, he spotted a small nail within reach, and used that to pick the horse padlock that was used to fix the chain to the staple in the floor. He used the freedom initially simply to stretch his legs, and to have a chance to sleep properly, rather than fixed to the chair, but one day his keepers came back in to check on him before he had a chance to get back into position. After he showed the jailers the ease with which he had picked the lock, they added a pair of handcuffs to his restraints. Sheppard desperately begged them not to do so, and even his former master, from whom he had stolen some of the items for which he was going to be hanged, tried to persuade them not to handcuff him.

It was all an act: Sheppard knew full well that he could slip the handcuffs without any difficulty, but he wanted to lull the keepers into a false sense of security. Within minutes of them leaving him, he had removed the cuffs but made sure that they were always on when he was being monitored. He even chafed the skin around his wrist to make it look as if he had been trying to remove them, in an effort to gain sympathy from his jailers, but to no avail (although some of his visitors took pity and gave him money).

On Wednesday 14 October, the sessions began once more, and that morning there was an uproar when Jonathan Wild’s throat was cut in the courtroom by one of Sheppard’s fellow thieves, Blueskin Blake. Much to the annoyance of many, including Sheppard, Wild wasn’t killed, but was seriously injured, and in the aftermath of the attack, the attention of the keepers at Newgate was diverted. This made it an ideal time for Jack Sheppard to carry out his escape.

On the afternoon of 15 October, around 3 p.m., Sheppard slipped his handcuffs and then broke a link in the chain holding him to the floor. He pulled the shackles further up his legs so they wouldn’t impede his progress, then made a hole in the chimney of the room. From there he was able to pull out an iron bar, about two and a half feet long, and an inch square. With that he broke through the ceiling of the Castle, and pulled himself up into the Red Room, which had been used years before to hold prisoners captured after the Battle of Preston during the 1715 Rebellion. The room and its doors hadn’t been used in seven years, so Sheppard had to remove a nut from the lock before he could go further.

In the Red Room, he also found a large nail on the floor, which became very useful as he progressed through the upper floors of Newgate prison. He had to break through the wall to get at the bolt that held the door to the chapel fastened, but was lucky that no one imprisoned nearby heard him. In the chapel, he broke off one of the iron spikes, and proceeded to attack the door between the chapel and the leads (the area of the roof covered by lead sheets). The next door was very securely fastened with a heavy lock, and although he was disheartened for a few minutes, he finally regained his composure and set to work. Between the nail and the spike, he made short shrift of the padlock, and got through it.

It had taken him five hours to get this far, and he heard the clock at St Sepulchre’s chime eight as he broke through yet another door, which had more bolts, bars and locks than any of its predecessors. Initially he tried to break through the lock, but when that proved impossible, he attacked the door itself – and the lock came away from the wall.

Sheppard was now one door away from the outside; the Newgate authorities didn’t think anyone could get this far without permission, so it was only bolted on the inside. It was the work of a second for Sheppard to climb through it, out onto the roof. He clambered up the roof and looked over the wall, working out where his best exit point would be. The shops outside the prison were still open, so he had to be especially careful that he didn’t screw up the escape at this late stage.

He headed back down to the Castle and collected the blanket that had been placed over him at night. His luck continued to hold: one of his visitors from the afternoon had promised to return that evening but hadn’t done so, so the alarm still hadn’t been raised – the guards were still dealing with the disturbances that had followed the attack on Jonathan Wild the previous day. He retraced his steps to the leads, fixed the blanket with the spike from the chapel to the wall of Newgate, and used it to drop down onto the roof of one of the houses next to the prison, owned by a turner named William Bird.

Sheppard tried to creep softly down the stairs from the garret of the house – luckily, the door to the roof had been left open – but the woman of the house heard his irons clinking together. Rather than risk capture, Sheppard hid in the garret for a couple of hours, and around 11 p.m., made his way downstairs. When a visitor to the house left three-quarters of an hour later, Sheppard followed him out, omitting to shut the outer door behind him. To his own surprise, he was a free man once more.

The next two hours were spent heading away from Newgate, and around 2 a.m., he found himself in Tottenham Court, where he hid in an old house in the fields for a few hours. He was still wearing the fetters around his legs, which were beginning to swell and bruise as a result of the physical punishment they had endured. He stayed hidden throughout the Friday – it poured with rain all day, so no one came looking for him. That evening he used some of the money that he had been given by visitors to his cell to buy some cheese, bread and beer, but the chandler’s shop at which he purchased his necessities didn’t have a hammer available. He spent Saturday the same way, and on Sunday morning ran out of patience, and tried to break through his fetters with a large stone.

On Sunday, the owner of the house found him, and was immediately suspicious when he saw Sheppard’s chains. The fugitive spun him a story about being sent to Bridewell prison for not providing support for a bastard child, which the man accepted although he asked Sheppard to leave. Later that day, Jack tried the same story on a shoemaker, who got hold of a hammer and a punch from a blacksmith, in return for the quite considerable sum of twenty shillings, and broke through the fetters. The manacles and leg irons eventually ended up in the possession of Kate Cook, another of Sheppard’s mistresses.

Sunday night saw Sheppard disguised as a beggar staying in Charing Cross, and taking great pleasure in talking about his own exploits. His escape was the only topic of conversation; he was already the subject of various ballads, which he delighted in listening to during his wanderings through Piccadilly and the Haymarket the following day.

Sheppard stayed free until the night of 31 October. He had promised his mother that he would do his best to leave England – although he had no intentions of doing so – and she had even gone to St James’ Palace to try to gain a pardon for her son. Jack wrote a letter to his friend Blake who was still confined in Newgate, urging him “if thou art still a man, [to] show thyself such, step forth, bilk the prigs, and return to thy confederate and dear friend”. (Blake did try to escape but without success.) He broke into a pawnbrokers in Drury Lane, and used the items he stole to dress as a dandy and parade around town. He went out on the town with two of his mistresses, and invited his mother to join them. Despite everyone warning him that he was being foolhardy, Sheppard got progressively more drunk, and by the time the inevitable happened, and the officers of the law caught him, he was incapable of resisting.

He was returned to Newgate, where this time they were taking no chances. In addition to the handcuffs, fetters and chains, two guards were constantly with him, day and night. He received a procession of visitors, including many of the nobility, whom he begged to plead with the king for a pardon, or at the very least a commutation of his death sentence to transportation (his brother Tom had been transported shortly before Jack escaped from Newgate).

Sheppard was given an opportunity to cheat the hangman, when he appeared before the Court of King’s Bench on 11 November. He begged for a pardon, and was told that the only way that he would receive clemency was if he would name his associates in his last escape. For once, Sheppard told the truth: no one except God Almighty had aided him. He was reprimanded for profanity, and his date of execution set for Monday 16 November.

Even at this late stage, Sheppard didn’t give up all hope of escape. On the morning of 16 November, he took communion, and was then taken down to the Newgate yard to be handed over to the executioners who would transport him to the gallows at Tyburn. To his horror, they insisted on handcuffing him, and he desperately tried to resist this, hitting out at the officers. After they had restrained him, the guards searched Sheppard’s pockets and found a small pocket knife: Sheppard had intended to cut through the ropes that were binding him for his final journey, and leap from the cart into the huge crowds that were lining the route from Holborn to Tyburn.

On the way to the gallows, the procession stopped to allow Sheppard to drink a pint of sack (a sweet wine fortified with brandy), and when they arrived at the place of execution, the thief passed over a piece of paper to someone in the crowd, which was believed to be the account of his life. He behaved with great decency on the scaffold, according to contemporary reports, but his slight build, which had been so useful to him during his escapes, told against him now, and he was slowly throttled to death by the rope as he hung there.