Jack Sheppard: Stone walls do not a prison make.

In researching my next Biographica Incognita entry I have been looking at impressive escapes from prison. This inexorably led me to the story of Jack Sheppard whose criminal career only lasted about two years but in those two years he accrued the notoriety of a lifetime.

Jack was born in March 1702 in Spittlefields, London which at the time was little more than a slum. The hardship his family were almost certainly experiencing can only have increased as his brother, sister and father all died within a couple of years of each other. Jack was sent to a workhouse at the age of six where he was apprenticed to a series of furniture makers and eventually apprenticed as a carpenter.

According to the biography by Lucy Moore by 1722 he was showing “great promise” as a carpenter. He is described as short and slight (about 5′ 4″) but deceptively strong. Other records suggest he was particularly pale with a slight stutter. Despite this he was immensely popular due to his witt and good nature. Reading between the lines Jack appears to have been a bit of a loveable rogue.

Frequenting some of the less salubrious drinking houses in London, Jack would later claim is what led to his descent into criminality. Looking at this through the lens of modern social analysis, Jack was a poor man from a poor family, by the age of twenty earning only an apprentices wages, with the ample illicit opportunities provided by the public houses of London’s East End and the company he would inevitably keep in that environment made a criminal career the path of least resistance.

So far I have just described a penniless young man who dropped out of his apprenticeship and spent a lot of time in the pub. Whilst there is social commentary enough here, this is only where Jacks story truly begins. He started going out with a sex worker called Elizabeth Lyon. Bess is an interesting character in her own right and probably deserves a dedicated post. She was Jacks sherpa up the steep incline that he would take to become a legend.

Jack started with petty theft, pocketing items from shops, or removing property from residences where he was employed as an independent carpenter. He never seems to have been caught for these minor crimes and that is probably what gave him the confidence to escalate. Jack however had gotten on the wrong side of Jonathan Wilde, the “Thief taker General” who it turns out was also the Don Corleone of eighteenth century London. Jack has previously refused to work for Wilde and subsequently used one of Wildes fences to move some stolen property.

Wilde arranged a less than elaborate set up in which Jack was invited out for a pint by a mutual friend and then handed over to a local constable. At a time before a recognisable police force when constables were part time and prone to minor bouts of getting stabbed to death, this guy must have thought all his christmases had come at once. All he had to do was sit in a nice warm pub any await the arrival of a criminal with a £40 bounty who had a reputation for being non-violent.

The Birth of a Legend

Jack was held on the top floor of St Giles Roundhouse to await further questioning. Consider this like local police station cells, secure and guarded. Reports on how quickly his escape was achieved vary but the longest estimate is three and a half hours. He had broken through the ceiling timbers, climbing to the ground whilst still wearing leg irons. By this time a crowd was forming outside as his escape had been noticed and was causing a fair amount of noise. He joined the crowd, pointed to a shadow on the roof and coolly shouted “hes up there” before walking away.

A month later Jack was caught picking a pocket and sentenced to a custodial sentence in Clackenwell prison which was a modern, state of the art, prison…..in 1724. Bess was with him as she was recognised as his wife at this point. They escaped within a couple of days. They had broken out of their leg irons and then escaped, first out of their cell into the prison yard and then over the seven meter high wall.

Where Jacks first escape went largely unnoticed by the press, this escape did not. London’s papers were littered with articles and cartoons of Jack and Bess. He became a folk hero overnight.

Wilde, receiving both pressure as London’s “Thief taker General” and desperate to remove Jack as competition focused his efforts on locating and arresting him. As there was no warrant for Bess, she had escaped but wasn’t held for any crime, it took Wilde no time to locate her, at which point he kept her plied with brandy until she disclosed Jacks location. He was hiding in the gin shop run by the mother of one of his criminal partners. Which frankly sounds like the ideal hiding place to me.

Jack stood before the magistrate charged with three counts of housebreaking. Interestingly I could find no suggestion of a charge of gaolbreaking. Of the three counts the first two were dismissed as having “insufficient evidence”, the third however was stacked with the full weight of Wildes resources, a parade of witnesses were presented to the magistrate as well as Wilde himself taking the stand. On this charge Jack was sentenced to death by hanging.

Jack got bored of waiting around in a cell whilst his sentence was being ratified, so he left prison again; Bess visited him with another sex worker, whilst they distracted the guards Jack loosened the iron window bars and escaped wearing woman’s clothing provided by Bess. I should stress its not explicitly stated and probably best not to speculate on how two sex workers chose to distract the prison guards.

He managed to evade escape for some time however was eventually found and arrested. The level of physical restraint placed upon him at this point was hilarious. He was placed in a strongroom in Newgate Prison called “The Castle”, literally wrapped in chains leaving only his head visible atop the pile of chains which were bolted into the floor. Whilst detained thus he was visited by dozens of people from all levels of society, he dictated an autobiography and a portrait was painted (unfortunately only the original sketches survive).

Jack got bored again, and so he left. Taking advantage of a disturbance in the court room next to the prison caused by Jonathan Wilde being stabbed during an active court session, Jack slipped his handcuffs off, picked the lock holding his chains (reportedly using a nail between his teeth), shuffled up the chimney, pried the iron bars sealing the chimney loose(all whilst still wearing leg irons). shuffled back down the chimney to collect the bedsheets from his cell, went back up the chimney, to the prison roof, used the sheets to climb down to a neighbouring house, broke into the house and walked out of the front door without waking the occupants.

Unfortunately Jack decided to celebrate his escape by stealing some money and posh clothes, going to his local pub and consuming a frankly athletic amount of alcohol. It didn’t take long for the constables to learn that he was on a bender in his favourite pub, they came and arrested him. This time Jack was weighted, chained, handcuffed and had a round the clock guard.

Jack Sheppard was hanged in Tyburn on 16th November 1724.


Jack was known as “Honest Jack” given he never hurt anyone, his demeanour even going to the gallows was warm, friendly and jovial. At the time when personal luxury items were increasingly popular with the middle and upper classes, the streets of London were awash with unemployed sailors and soldiers and alcohol was cheaper than food. Crime was skyrocketing Jacks popularity isn’t hard to understand.

I feel that any sensible man would have left London after his first escape. England had no centralised police force to follow him across districts but Jack comes across as such an endearing character due to his daring and apparent irreverence toward the laws and punishments directed at him. Times and attitudes changed but two hundred years later the story of Gentleman Johnny Ramensky who also escaped from “inescapable prisons” five times would excite the public imagination. Ramensky never seems to have gotten close to the level of public affection that Jack managed to cultivate.

That being said, in reading up on Jack Sheppard I found myself having to only use contemporary sources. Jacks legend was still very much alive after his death. In each retelling seems to have twisted and changed, constantly evolving to a point where if Jack heard it today he wouldn’t recognise the tale. The legend of Jack Sheppard has had three centuries to grow into something different. In the beginning was a smaller than average man from a poor family who just knew how to have a good time. Everyone loves a bit of civil disobedience and Jack Sheppard alloyed a legend out of civil disobedience and contempt for authority.

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