Today in London’s rebel past: Jack Sheppard escapes from Newgate Prison, 1724 (the first time).

“Whereas John Shepheard broke out of the Condemn’d Hold of Newgate (with his Irons on) by cutting off one of the large Iron Spikes over the Main Door on Monday the 31st of August last, about six a clock in the Evening, he is about 23 years of Age and about five Foot four Inches high, very slender and of a pale Complection, has lately been very sick, did wear a light Bob Wig, a light colour’d Cloth Coat, and white Waistcoat, has an impediment in his speech and is a Carpenter by Trade. Whoever will discover of apprehend him so that he be brought to Justice shall receive 20 guineas Reward to be paid by the Keeper of Newgate.”
(Proclamation from the Keeper of Newgate, 4th September, 1724.)

“A file’s worth all the bibles in the world…” (Jack Sheppard)

In his day he became the most famous name in England and he remained a folk-hero to the poor for over a century after his death. In the 1840s plays based on his life were still regularly being performed for working class audiences, and his name was better known amongst many of the poor than that of Queen Victoria. Jack Sheppard was the prison escaper supreme of eighteenth century England.

Born in Spitalfields in 1702, his carpenter father died during Jack’s childhood. His mother was forced by poverty to place him in Bishopsgate workhouse. Beginning a carpenter’s apprenticeship, he picked up some locksmithing skills that would stand him in good stead in later years…

“The apprenticeship system was still controlled by an Act passed under Queen Elizabeth, the Statute of Artificers. The system provided young people with a vocational education, in another household…. they were ‘bound apprentice’ between twelve and sixteen. Parish children might begin their apprenticeship as early as eleven, and continue in it until they were twenty-four. (Remember that the expectation of life at birth was then about 36 years.) The contract would continue for seven years or more, until the master was satisfied that the apprentice knew his trade. Apart from some public holidays, no home leave was given. The boy’s parents might not see him again until his time was up. Imagine the child of twelve leaving his home to live in strange surroundings with no parental love, withstanding the storms of adolescence and reaching physical maturity with only the recollection of his childhood and what support his master gave him to sustain him, and perhaps occasional letters from home if his parents could write.” (Restoration London, Liza Picard, 1997.)

But Jack rejected these narrow and constricted channels of apprentice life; with just ten months of his apprenticeship left to serve, he deserted the master to who he had been apprentied, Mr Kneebone, and joined the swelling ranks of the ‘idle apprentices’, a group that invoked fear and suspicion among respectable folk for many centuries – a leading moral bogey of the era.

Jack took to a life of robbery. It might be said that Jack wasn’t an especially successful robber, he was imprisoned five times – luckily he turned out to be a breakout artist par excellence, so that he escaped prison four times. These technically brilliant and daring escapades, as well as his taunting attitude to authority, secured his lasting fame among the working class.

In the spring of 1723 he aided the escape of his girlfriend Edgeworth Bess from St Giles’s Roundhouse. In April he ended up there himself; betrayed by his brother Tom (who was hoping to bargain his own release from a burglary charge) and his friend James Sykes, he was lured into a trap and delivered to a Justice Parry.

It took him less than three hours to escape.

That was in April 1724. From then until the end of November the saga of his escapes grew, astounding ever-increasing numbers of people for their daring and dexterity.”

Arrested again for pickpocketing a gentleman’s watch, Jack was now taken to Clerkenwell’s New Prison. As his common law wife, Edgworth Bess was allowed to join him from her confinement in the Roundhouse. They were locked in the most secure area, ‘Newgate Ward’, and Jack was weighed down with 28lb of shackles and chains. He soon set to work sawing through these and

then through an iron bar. Boring through a nine-inch-thick oak bar, then fastening sheets, gowns and petticoats together, they descended 25ft to ground level; only to find they had landed themselves in the neighbouring prison of Clerkenwell Bridewell! Undaunted, driving his gimblets and piercers into the 22ft wall, Jack and Bess used them as steps and hand-holds and made their way over the wall to freedom in the early morning of Whit Monday 1724.

While Sheppard’s later escape from the condemned hold of Newgate made ‘a far greater Noise in the World’, the London gaolkeepers regarded the New Prison escape as the most ‘miraculous’ ever performed in England, so they preserved the broken chains and bars ‘to Testifie, and Preserve the memory of this extraordinary Event and Villian.’

Jack spent the next three months of freedom engaging in highway robbery and burglary. He was recaptured after he robbed his old master, Mr Kneebone, who called in contacted Jonathan Wild, ‘the thief-taker General’. Wild was both a trainer of thieves and a deliverer of them to the courts, a fence of stolen goods and returner of them to rightful owners; “a complex and parasitic system” that “had in these years become a system of municipal policing.” Sheppard always refused to compromise himself by having any dealings with the repulsive and hated Wild.

Wild pressured Edgeworth Bess to reveal Jack’s hideaway, and, after an exchange of pistol fire, he was captured and taken to Newgate prison. In August he was tried and sentenced to hang.

On his return to Newgate he was locked in the Condemned Hold, a dismal cell next to the Keepers’ Lodge, and close to the prison gate. It had a stone floor, and a wide wooden shelf with a row of iron bolts above served as a communal bed for all inmates. Its narrow window faced onto the dark lane beneath Newgate’s famous arch.

Deputy Keeper Bodenham Rouse ordered Jack to be chained and fettered, but the chains were long enough to allow him to stand by the door and converse with visitors.

The Lodge acted both as a reception room for the prison, and a common room for the turnkeys and keepers, including a bar (run by Mrs Spurling, widow of head turnkey Spurling who had been shot in open court by a highwayman on trial 10 years before). From the table where they sat drinking the screws could keep an eye on those who passed in and out of the prison yard, as well as on the ‘Stout partition” that separated them from the prisons in the Condemned Hold.

In the last week of August, Jack’s ‘death warrant’ arrived, setting a date on September 4th for his execution at Tyburn. He had only a few days to escape if he was to avoid being ‘turned off’.

Jack had previously, according to his own later account, agreed a plan to break out with his three cellmates, but they had pulled out when it looked like they might be reprieved; Jack had also fallen ill with a fever. But on the day before their scheduled execution, news arrived that the reprieve was not forthcoming. One of the men, Davis, gave Jack all the tolls he had had smuggled in by friends, with a view to freeing himself. He and the other two cons then departed for their appointment with the gallows. Jack, determined not to share their fate, set to work with filing away at the spikes set in the top of the partition separating the lodge from the Hold. After two days filing (halting only when visitors or turnkeys passed by) he had filed halfway through the spike. Another day’s work would see it weakened enough to be readily snapped off, he thought, leaving him able to pull himself free through the gap.

However, the next day was Sunday, when crowds of visitors flocked to Newgate, passing in and out of the Lodge all day. Jack was unable to get much filing done. He dared not do it at night as the quiet made the noise stand out and he feared the screws would hear. On Monday morning he resumed his task…

By noon, when Edgeworth Bess and her friend Poll Maggot came to visit him, he was close to achieving his goal. As they talked and laughed he continued filing away. Cruikshank’s illustration (above) hints at how precarious this was, with the screws sitting only a few yards away around a corner. Around six in the evening he managed to snap the spike off, leaving a gap; though only around nine inches square, this was enough for the wiry Jack to wriggle through, dressed in a disguise of a booney and gown Bess had pushed through to him. Pulling himself up on the neighbouring spikes, he edged his way out, lowering himself down into the Lodge. Poll Maggot hid behind a pillar, and Bess and Jack sauntered out past the turnkeys seated at the bar, who he later commented were ironically discussing Jack’s own previous escape from the New Prison, and how they would have not allowed it to happen in THEIR jail. Two women had arrived and two were seemingly leaving, chattering and laughing…

Reaching the street without being challenged, Jack and Bess ran to a waiting coach driven by Jack’s mate William Page, to be joined by Poll Maggot, who had also walked out of the jail without incident. Driven to Blackfriars Stairs, they hired a boat which took them to Westminster… In a Holborn inn, Jack sawed his chains off, fortified by a bottle of brandy. He was free once more… He walked through the City to Spitalfields where he spent the night with Edgworth Bess.

Sheppard’s latest escape threw the shopkeepers of Drury Lane and the Strand into a panic. Jack took up robbing again, this time from a watchmaker’s shop in Fleet St.

In the meantime, the Newgate authorities were seriously embarrassed by Jack’s escape, and the mockery and bad publicity it gathered them: the Daily Journal called the breakout ‘the most surprising Accident at Newgate’, and penny ballads appeared rapidly, taking the piss out of the jailers, or accusing them of letting Jack go for bribes.

However, Jack was re-arrested on September 9th, after he had been recognised around London by various people that knew him, and rumours had spread. He legged it to Finchley Common, but a posse of Newgate turnkeys trailed him there and arrested him and his mate Page. Jack was returned to Newgate once again, and locked once more in the Condemned Hold – this time chained to the floor and heavily guarded.

By this time Sheppard had become a celebrity and folk hero of the labouring classes; visited by the famous and interviewed by journalists and ballad makers. He offered some lucid comments; when urged by a prison official to concentrate on preparing himself for the afterlife rather than attempting to escape, he replied “One file’s worth all the Bibles in the world.” He also condemned the corruption and hypocrisy of the criminal justice system.

As his trial approached Jack implemented his escape plan on the 14th October. This amazing flight from Newgate was to make him an enduring legend amongst the working class for over a century afterwards. Freeing himself from his shackles he then worked his way up the chimney, through several locked rooms and eventually on to the roof and over the wall to freedom.

On 29th October Sheppard robbed a pawnshop for some spending money and began a triumphant tour, a defiant spree through his old haunts and hunting grounds. He hired a coach and, with some female companions, toured his own native Spitalfields – he also drove through the arch of Newgate itself! Defiantly parading himself around the ale-houses and gin-shops, he was recaptured after fifteen days of glorious liberty.

Jack Sheppard was hanged on 16th November 1724 at Tyburn; a cheering crowd, said to number 200,000, lined the route to salute him. A last minute escape plan was foiled, and attempts to rescue his body to preserve it from dissection by surgeons prevented plans to bring him back to life…

Jack’s short and eventful life may have been cut violently short – but his defiance of authority and his resourceful ability ensured his fame has outlasted him for nearly three centuries.


An entry in the
2017 London Rebel History Calendar – check it out online.

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