The Mammoth Book of Prison Breaks

by Paul Simpson

  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.

  Even at this stage, Sheppard still had one plan up his sleeve – one last desperate throw of the dice. After fifteen minutes, his body was cut down, and the idea was that his friends would take it away and transport it rapidly to a doctor’s surgery, where blood would be let from the “corpse” allowing it to revive. Unfortunately, there was such interest in the hanging, and such a large crowd, that by the time his friends reached the body, it was too late. His remains were taken to a pub in Long Acre, and then buried in the churchyard of St Martins in the Fields that evening.

  Sheppard’s escape from Newgate became the benchmark for such daring feats over the next couple of centuries; in Bram Stoker’s Dracula, the character of Renfield is imprisoned, and apparently “Jack Sheppard himself couldn’t get free from the strait waistcoat that keeps him restrained”. As the Newgate Calendar noted, “A great warrior could not have received greater attention than this famous criminal.”

  Sources:

  Rictor Norton, Early Eighteenth-Century Newspaper Reports: A Sourcebook, “Jack Sheppard, Jail-Breaker”, 9 October 2003

  Moore, Lucy: The Thieves’ Opera (Viking, 1997)

  Ainsworth, William Harrison: Jack Sheppard A Romance (Project Gutenberg reprint, 2005 from the 1922 edition)

  Grovier, Kelly: The Gaol (John Murray, 2008)

  Heppenstall, Raymond: Tales from the Newgate Calendar (Futura, paperback edition, 1983)

  Anchoring the Giant

  Ronnie Biggs and his fellow participants in the Great Train Robbery in 1963 weren’t the first train robbers to make a habit of escaping from prison. Nearly seventy-five years earlier, the perpetrator of one of the most daring locomotive raids was also a veteran escape artist. Oliver Curtis Perry brought “Wild Western Ways” to the Empire State of New York in the 1890s, and spent many years in and out of jails as a result.

  Described by the Utica Saturday Globe after one of his escapes as “the King of Desperadoes” and “the most sensational and daring train robber and all around criminal of the nineteenth century, outdoing Jesse James in cunning and boldness”, the twenty-six-year-old Perry was responsible for a raid on the “American Express Special” on the night of 29 September 1891, a train running from the New York state capital, Albany, out towards Buffalo. The carriage which he targeted was carrying cash, bonds, jewellery and valuables – sometimes a million dollars’ worth – guarded by one messenger (who, to be fair, was armed). Rather than the brute-force methods used by robbers in the Wild West, though, Perry had been cunning: he had sawn a hole in the door of the carriage, squeezed through, and then held up Burt Moore, the messenger. Once he had filled bags with his loot, Perry had retreated through the hole, swung beneath the carriage to cut through the air-brake, and thus stopped the train. He had then vanished into the dark canyons near Utica.

  The Pinkerton’s National Detective Agency was put on the case, with Robert Pinkerton himself taking a hand in the investigation. Although they announced that they had “a pretty good clue” to the robber, their enquiries stalled until one of the train crew believed that he had recognized Perry, who used to work on the New York Central Railway before an accident had left him penniless and unemployed. Many of Perry’s friends from the city of Troy, where he had lived in the two years before the case, spoke out in his defence: they admitted that he had been a wayward youth, but was now on the straight and narrow. City Missionary and Sunday School teacher Miss Amelia Haswell, who had tried to reform Perry, was particularly noticeable in her spirited comments on his behalf. Perry himself wrote to the detectives in December to clear Burt Moore of any involvement in the robbery; although the letter was postmarked Guelph in the neighbouring province of Ontario, Canada, no one could trace any other sign of Perry there.

  Perry hadn’t taken anywhere near as much as he might have done from the robbery – American Express originally tried to claim it was as little as $150, but a figure nearer $5,000 seemed more likely – and when this ran out, he decided to visit what he had come to regard as his own private bank for withdrawals: the American Express Special. On 20 February 1892, he struck again. This time, however, it did not go so smoothly.

  The problems began when Perry jumped onto the wrong carriage initially and had to make his way along the roof to the money car. Rather than reuse the stealth tactics he had employ
ed the previous September, the robber simply broke the glass window of the carriage, and pointed his gun at the American Express messenger, Daniel McInerney. Unlike Moore, McInerney was ready to defend the goods in his charge: he pulled his gun, but as he fired, Perry did the same, his bullet hitting the messenger’s gun, sending it flying and breaking his fingers. McInerney reached for the air-whistle cord, but it failed to work both times he tried. He then kicked out the lamp as Perry fired again. This shot grazed McInerney’s temple; a third hit him in the thigh.

  Although he was concerned at McInerney’s injury, Perry was far more worried by the fact that he couldn’t find any cash in the car. A desperate search didn’t reveal any, and as the train slowed down, Perry abandoned the hunt, and swung himself back up onto the roof. McInerney and the conductor, who had been alerted by a faint sound from the air-whistle, believed that he must have jumped off when the train slowed down. Getting rid of the disguise he had worn for the robbery, Perry coolly climbed back into the Express and waited until it reached its next proper stop, in Lyons. There he jumped off, wandered around the station, and onto the platform, as if he was simply waiting for a passenger to arrive. Unfortunately for Perry, the conductor recognized him and realized that he must be the robber. Perry hijacked a coal train and tried to flee, but the Express engine was uncoupled, and it set off in pursuit. After running out of steam, quite literally, Perry abandoned the coal train and headed across country, stealing a horse. That put not just detectives but local angry farmers on his trail, and after a chase he was eventually arrested and taken to Wayne County Jail in Lyons. His career as a train robber was over; his time as an attempted escapee was just beginning.

  While Perry waited for his trial, he became an object of curiosity to the locals, particularly members of the press. He elected to defend himself, and was remanded for an appearance before a Grand Jury. However, much as he may have appeared to be enjoying the cut and thrust of the debate in court, Perry was determined to escape. His father came to visit him in jail, and was searched on his departure: to the surprise of the authorities, this respectable builder had a drawing in his pocket, with a note in Perry’s handwriting explaining the exact dimensions and shape of key that were required to unlock the corridor door within the jail. Instead of receiving a key back, Perry found his ankles shackled with heavy iron cuffs connected to an eight-inch-long log chain, and his father banned from visiting him, despite his protestations that he knew nothing of the paper.

  Perry didn’t seem too fazed by his new restraints: “I think you ought to get a jail strong enough to hold me without this. I ain’t very hard to hold,” he told his warders, who noticed that their prisoner’s thin legs almost seemed to slip out of the shackles. A new closer-fitting pair was created, leading to Perry claiming that the Lyons jailers must be afraid of him “for they anchor me down as if I was a giant”.

  He continued to play up to the public image that was being created of him as a charming gentleman crook, all the while planning his next escape. He worked with other prisoners to create a lead key for the corridor door, but he was caught while trying it out. During the thorough search of the prison that followed, the sacking was removed that had been wrapped around his shackles to stop them from rattling – and the shackles fell in two. Perry had been able to cut them apart using a saw that he kept hidden inside a Bible. Inside his clothes, the Sheriff found five $50 bills sewn into the lining, a reserve kept in case of emergencies – or for bribing guards.

  Perry was moved into a smaller cell, and watched even more carefully. He was kept apart from the other prisoners and his meals were passed through a hatch in the cell door. In his desperation to get out, he tried to break his new shackles by dropping one of the legs of his iron bed onto them; instead, he ended up with his wrists shackled as well.

  When he was finally put on trial, Perry pleaded guilty, on the advice of Amelia Haswell, who was convinced that he would receive a lighter sentence as a result. He didn’t: Perry was given forty-nine years and three months in total, of hard labour, the various component parts of his sentence to be served consecutively. Even with remission for good behaviour, it would be 1921 before he would see freedom.

  Perry was sent to Auburn Prison to serve his time. It had been built in 1816, and saw the first execution by electric chair in 1890. It lent its name to the Auburn System of prison governance, under which inmates kept silent at all times, and moved around in the “lockstep” – each man shuffled forward, holding the shoulder of the man in front. Although Perry quickly fell foul of the system, the authorities believed that they had broken him after he served time in solitary confinement.

  They were wrong. Placing him in the centre of a row of cells, and ordering no one to speak to him might have kept Perry isolated, but it didn’t stop him planning. He was kept in the cell twenty-four hours a day with no contact with guards or prisoners, but on Sunday 23 October 1892, Oliver Perry escaped, after digging a hole in the twenty-two-inch thick dividing wall between cells. His neighbour was assigned to the prison tailor workshop, so his cell door was left open when he was at work. Perry had been concealing the hole with a towel, and after having supper, he had nonchalantly gone through the hole, through the open doorway, and out into the corridor. Since all the other prisoners were at work, there was no need for a lot of guards on the prison wing; Perry was easily able to avoid being seen by the single warder on duty. Getting out into the yard, he hid in an outhouse, waiting for dark, so he could scale the wall and escape.

  When his flight was discovered, the prison was turned upside down, but no one could find any trace of Perry. However, later that evening, he was spotted as he crept across the yard, and one of the warders hit him so hard that his nightstick broke. As a result of the failed escape attempt, just under ten years of remission was removed from his sentence, meaning he would be in jail for at least forty years. He continuously found himself in trouble with the authorities, culminating in a forty-four-day stretch in the dungeons. After that, he became increasingly violent, and although there were some who believed that he was putting on an act to get out of Auburn, on 27 December 1893, he was declared insane. It’s interesting to note that the doctor certifying him pointed out to the authorities at the asylum, “He is a desperate man, and you cannot be too careful, or he may well escape from your place.”

  He was sent to the Matteawan Asylum for Insane Criminals, which had only opened a year earlier, and found himself immediately in a cell on an isolation ward. The outer walls of the block had a lining of sheet iron between its brick layers, there were wire shutters and iron bars on the windows, and the ceilings had been held in place with stone flagging. The cell doors were made of two-inch-thick oak, and the locks didn’t go all the way through. Prisoners could be watched day or night for any signs of faking. While Perry’s release date from Auburn might have been four decades in the future, at least there he had an end in sight. Those sent to Matteawan were there for an “indeterminate sentence” according to the asylum’s superintendent, Dr Henry Allison.

  For eighteen months, Perry put up with the regime. He was allowed visitors, including Amelia Haswell, and complained about the conditions at the asylum. In April 1895, he decided enough was enough. On the night of the ninth, as night watchman Carmody came in to do his rounds, he was set upon and relieved of his keys by three of the inmates.

  Perry had been alerted to a possible escape route when one of his fellow prisoners, Patrick Maguire, told him that a long ladder had been left in the prison chapel by workmen who were repairing the ceiling. Perry had been overseeing the creation of keys for the doors from the iron spoons that some men in the isolation ward were issued with in place of knives and forks for their meals. Maguire had been a jeweller as well as a burglar, and was able to make a small saw from a thin strip of steel that was inside the sole of the prison-issue slippers, and used this to adjust the keys into the necessary shape. Although the two locks on each door were different, one pair of keys opened all the doors in
the corridor.

  Maguire was able to pass a bottom lock key to another prisoner, Frank Davis; on his way to supper, Davis unlocked the bottom lock of Maguire’s cell. Once the warder had carried out the post-meal inspection, Maguire had cut through the strands of wire mesh on the cell-door peephole, stuck his arm through and used his key to open his top lock. Letting himself out, he went across the corridor to Davis’s cell, opened the top lock, and took the bottom lock key back from Davis, thus letting him out. They then unlocked Oliver Perry’s cell. Thus when the warder came down the corridor to answer one of Perry’s perennial complaints, he was startled to find that three of his charges were free to attack him. They covered his mouth to stop him raising the alarm, and pushed him into Perry’s cell, where his mouth was stuffed with rags and he was tied to the bed frame.

  Using the warder’s keys, Davis, Maguire and Perry released two other prisoners, John Quigley and Michael O’Donnell, and let themselves through the ward door, locking it behind them. They moved softly past the attendants’ rooms, and up to the chapel, unlocking the door with the warder’s keys again. Once inside, they used the ladder, which was still in position, to reach a small hatch in the ceiling which led to an attic. The dormer window wasn’t securely fastened, and was quickly opened, allowing them to head out onto the roof. From there it was the work of seconds to reach iron drainpipes and shin down them.

  Even though they were spotted as they reached ground level, the five men were able to get away, still wearing their asylum uniforms, with no proper shoes. Quigley only managed to stay on the run for two days, before he was picked up on Good Friday, begging for food. Maguire and O’Donnell were found forty miles from Matteawan very shortly afterwards. Frank Davis survived for five days, but he too was returned to Matteawan.