Today in London’s rebel history: Jack Sheppard breaks out from Clerkenwell New Prison, 1724.


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. Jack Sheppard was the prison escaper supreme of eighteenth century England.

Just last week I saw Otherstory’s very fine puppetshow ‘Escape Was One’s Mind’, which told Jack’s story in brilliant and stark theatre (See here to catch an upcoming show).

Born in Spitalfields in 1702, Jack’s father died during his childhood, and his mother’s poverty led to Jack being placed in the Bishopsgate workhouse. Beginning a carpenter’s apprenticeship, he picked up some locksmithing skills, which would stand him in good stead in later years

Maybe a childhood in the workhouse left him with a strong aversion to the bonded labour and confining straits of apprentice life, Jack deserted his master, and joining the swelling ranks of the ‘idle apprentices’ (a group that invoked fear and suspicion in the 18th century), he took to a life of robbery.

Not an especially successful robber, he was imprisoned five times – luckily he turned out to be a breakout artist par excellence, – and 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.

The London trades were undergoing a series of transformations as a result of new technologies and the expanding economy. New machinery was deskilling some, factory methods of organisation were making the protective practices of the Craft guilds obsolete and these were changing the relationship between apprentices and their masters. Depending on their trade and circumstances some masters began to fulfil one or more roles simultaneously – they might be working craftsmen, workshop overseers, shopkeepers, or wholesale suppliers. Equally they might be expanding into factory ownership or begin farming out piecework to home workers – or they could be in the process of declining into deskilled casual labour. So the artisan class was fragmenting and reforming in both upwardly and downwardly mobile directions. Crime was as legitimate a way as any to survive

After deserting his apprenticeship Jack took with enthusiasm to a life of robbery; he was imprisoned five times and escaped four. It was these technically brilliant and daring escapades, as well as his taunting attitude to authority that secured his long reputation among the working class.

The London trades were undergoing a series of transformations as a result of new technologies and the expanding economy. New machinery was deskilling some, factory methods of organisation were making the protective practices of the Craft guilds obsolete and these were changing the relationship between apprentices and their masters. Depending on their trade and circumstances some masters began to fulfil one or more roles simultaneously – they might be working craftsmen, workshop overseers, shopkeepers, or wholesale suppliers. Equally they might be expanding into factory ownership or begin farming out piecework to home workers – or they could be in the process of declining into deskilled casual labour. So the artisan class was fragmenting and reforming in both upwardly and downwardly mobile directions. Crime was as legitimate a way as any to survive.

After deserting his apprenticeship Jack took with enthusiasm to a life of robbery; he was imprisoned five times and escaped four. It was these technically brilliant and daring escapades, as well as his taunting attitude to authority that secured his long reputation 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 1724 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. “He was confined in the top floor. He cut through the ceiling, untiled the roof, and with the aid of a sheet and blanket lowered himself into the churchyard, climbed a wall, and joined a gathering throng which had been attracted to the scene by the falling roof tiles.

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, May 25th, 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. Kneebone 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.” (Peter Linebaugh) Sheppard always refused to compromise himself by having any dealings with Wild, either for fencing goods or in attempt to gain more lenient sentences in court. 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 the day his death-warrant arrived he implemented his escape plan; dislodging a spike, he inserted himself into a small hole he had worked in a wall and with the help of visitors was pulled through to freedom. 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. But he and his accomplice were recognised so they left London for Finchley Common. They were pursued and soon apprehended – Jack was taken to Newgate once again.

By this time Sheppard was 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 emphasised his preference for the tangible, saying ‘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! 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, to see him try and escape (tools were seized from him at the last minute), and to rescue his body from the clutches of the surgeons who received the bodies of the hanged for dissection.

But the story doesn’t end there… The tale of Jack was retold, re-written, spread throughout the world… 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.

John Gay seized upon the story, and reshaped it as the ‘Beggars Opera’, in which the figure of Mr Peachum is Jonathan Wilde merged with the corrupt PM Robert Walpole… This stark comparison between the acquisitiveness of the rich and the crime of the poor, was reworked by Bertolt Brecht and Kurt Weill 200 years later as the Threepenny Opera

Jack is almost an archetype, a popular creation, an ideal born out of an 18th century oppositional culture. Out of the class divide, between small number of the very rich, getting richer, and an increasing number of poor and labouring classes, crammed in London, trying to survive by hook or by crook… More and more people were crowding into the city, as enclosure forced people off the land, or coming from desperate poverty in Ireland Scotland or the north, in search of work or a foothold. In the early 18th century, the blatant corruption of the oligarchy in particular enraged people of all classes below them, and the breakdown of traditional relations, the seesawing economy, bred rebelliousness and riotous anger. The mob (more accurately, any one of a number of overlapping ‘mobs’) were easily roused to riot over almost everything. Demagogues, Jacobites, high churchmen, bigots and xenophobes, all sought mob support for their causes; and a very real opposition to the establishment, especially hatred of Walpole, led to numerous outbreaks.

But this was very much a pre-industrial rebelliousness, a turbulent, unruly proletarian street culture, not yet disciplined by the industrial revolution, with the work ethic not yet fully beaten into people and internalised by the likes of the Methodists (and London always had a stubborn lumpen ethos, never totally brought into Methodist respectability even in radical politics, unlike the northern towns where chartism etc flourished).

In parallel though, there was no real sense of a party or movement, no collective organization on a political level. (There were lots of trade combinations, by workers, though illegal and harshly punished). The Government shut down all criticism and opposition, even satire… imprisoning people for seditious libel for questioning or even mocking the political establishment.

So Jack’s rebellion is very individual, never crystalising into anything more collective; and is very much of its time, when the romantic rebel, the daring and stylish criminal could easily become a celebrity hero, like the highwaymen robbing with panache and dying with a flourish.
Although Jack’s story survived into victorian times, it’s likely he would never have become a celebrity in the same way a hundred years later, in an age where temperance and self-improvement had more sway.

But did the pose of romantic hero affect him after he became famous for his first escapes? Did the adoration of the crowd, the prison visits by the rich and leading journalists, painters etc and so on, swell his head? On the other hand, he is presented as being principled and clear-headed – disdainfully rejecting of religion, his refusal to deal with the repulsive gangmaster/fence/grass Wild… he also seems to know that in the end he is doomed, failing to leave London when he had the chance, in fact, doing the opposite, returning to his haunts, driving in a carriage through the outer gate of Newgate… in defiance, almost fatalistic bravado… But where would he have gone anyway? His only support networks being in London’s slums and taverns; he was as good as dead without them anyway.

His escapes from Newgate in particular made him an idol, because this prison was the most potent centre of repression, punishment and death, feared and hated by the lower orders like none other. Only Tyburn, the nagging tree itself, rivaled Newgate as a symbol of the class nature of punishment, law and the whole weight of hierarchical society. (It would be interesting to know which had more sarcastic nicknames among London’s lower classes – slang terms for being hung, and for Newgate itself, were almost numberless). Jack’s two breakouts from Newgate made the authorities look stupid, undermined the fear and terror, which enraged and scared the establishment that relied in the fear that the prison imposed – but delighted the classes subject to the gaol’s hospitality… Was his name shouted, did his ghost walk, as 56 years later, the London crowd burned Newgate to the ground in the Gordon Riots and freed hundreds of its inmates?

Jack Sheppard fascinated Londoners at the time, and since, partly because his story brings together so many crucial elements: he personifies the moral panic of the idle apprentice, the upper class terror of the lower orders, the sheer class hatred of the poor for the rich – and the vicious merry-go-round of crime and punishment, of law made and administered by the propertied, in their interests, against those with nothing.


An entry in the 2016 London Rebel History Calendar – check it out online

Past Tense have also produced a poster commemorating Jack Sheppard to coincide with Otherstory’s puppetshow, it is available from our publications page.



  1. janet · 22 Days Ago

    Jack Sheppard was my great, great, great, great, great uncle, his brother Thomas was my 5th great grandad.


    • mudlark121 · 20 Days Ago

      Cool! Hope you’re proud of him… 100 years after his death children in east London could recite all his escapes who didn’t know name of the reigning monarch in their own time… that’s proper applied knowledge…


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