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Jack Sheppard, Highwayman

January 18, 2020
by the gentle author

On the morning of 4th September 1724, an inconsequential thief named Jack Sheppard was to be hung at Tyburn for stealing three rolls of cloth, two silver spoons and a silk handkerchief. But instead of the routine execution of another worthless felon, London awoke to the astonishing news that he had escaped from the death cell at Newgate.

With the revelation that this was the third prison break in months by the handsome boyish twenty-two year old Jack Sheppard, he flamed like a comet into the stratosphere of criminality – embodying the role of the charismatic desperado to such superlative effect that his colourful reputation for youthful defiance gleams in the popular imagination two centuries later.

In the Spring, he broke out through the roof of St Giles Roundhouse, tossing tiles at his guards. In the Summer, with his attractive companion Elizabeth Lyon, he climbed through a barred window twenty-five feet above the ground to escape from New Bridewell Prison, Clerkenwell. And now he had absconded from Newgate too, using a metal file smuggled in by Elizabeth and fleeing in one of her dresses as disguise. Sheppard was a popular sensation, and everyone was fascinated by the inexplicable mystery of his unique talent for escapology.

Spitalfields’ most notorious son, Jack Sheppard, was born in Whites Row on 4th March 1702 and christened the very next day at St Dunstan’s in Stepney, just in case his infant soul fled this earth as quickly as it arrived. Unexceptionally for his circumstances and his time, death surrounded him – named for an elder brother that died before his birth, he lost his father and his sister in infancy. When his mother could not feed him, she gave him to the workhouse in Bishopsgate at the age of six, from where he was indentured to a cane chair maker, until he died too. Eventually at fifteen years old, he was apprenticed to a carpenter in Covent Garden, following his father’s trade, but at age twenty he met Elizabeth Lyon, his partner in crime, at the Black Lion in Drury Lane, a public house frequented by criminals and the infamous Jonathan Wild, known as the “Thief-taker General.”

On 10th September 1724, Sheppard was rearrested after his break-out from Newgate and returned there to a high security cell in the Stone Castle, where he was handcuffed and fettered, then padlocked in shackles and chained down in a chamber that was barred and locked. Yet with apparent superhuman ability – inspiring the notion that the devil himself came to Sheppard’s assistance – he escaped again a month later and enjoyed a very public fortnight of liberty In London, eluding the authorities in disguise as a dandy and carousing flamboyantly with Elizabeth Lyon, until arrested by Jonathan Wild,  buying everyone drinks at midnight at a tavern in Clare Market, Lincoln’s Inn Fields. Back in Newgate – now the most celebrated criminal in history – hundreds daily paid four shillings to visit Sheppard in his cell, where he enjoyed a drinking match with Figg the prizefighter and Sir Henry Thornhill painted his execution portrait.

Two hundred thousand people turned out for Jack Sheppard’s hanging on 16th November, just two months since he came to prominence, and copies of his autobiography ghostwritten by Daniel Defoe were sold. Four years later, John Gay’s “The Beggar’s Opera,” with the character of Macheath modelled upon Sheppard and Peachum based upon his nemesis Jonathan Wild, premiered with spectacular success. Biographical pamphlets and dramas proliferated, with Henry Ainsworth’s bestseller of 1839 “Jack Sheppard” – for which George Cruikshank drew these pictures – outselling “Oliver Twist.” Taking my cue from William Makepeace Thackeray, who wrote that, “George Cruikshank really created the tale and Mr Ainsworth, as it were, merely put words to it,” I have published these masterly  illustrations here as the quintessential visual account of the life of Spitalfields’ greatest rogue.

And what was the secret of his multiple prison breaks?

There was no supernatural intervention. Sheppard had outstanding talent as a carpenter and builder, inherited from his father and grandfather who were both carpenters before him and developed during the six years of his apprenticeship. With great physical strength and a natural mastery of building materials, he possessed an intimate understanding of the means of construction of every type of lock, bar, window, floor, ceiling and wall – and, in addition to this, twenty-two year old Jack Sheppard had a burning appetite to wrestle whatever joy he could from his time of splendour in the Summer of 1724.

Mrs Sheppard refuses the adoption of her little son Jack


Jack Sheppard exhibits a vindinctive character.

Jack Sheppard committing the robbery in Willesden church.

Jack Sheppard gets drunk and orders his mother off.

Jack Sheppard’s escape from the cage at Willesden.

Mrs Sheppard expostulates with her son.

Jack Sheppard and Blueskin in Mr Wood’s bedroom.

Jack Sheppard in company with Elizabeth Lyon escapes from Clerkenwell Prison.

The audacity of Jack Sheppard.

Jack Sheppard visits his mother in Bedlam.

Jack Sheppard escaping from the condemned cell in Newgate.

The first escape.

Jack Sheppard tricking Shortbolt, the gaoler.

The second escape.


Jonathan Wild seizing Jack Sheppard at his mother’s grave in Willesden.

Jack Sheppard sits for his execution portrait in oils by Sir James Thornhill  – accompanied by  Figg the prizefighter (to Jack’s right), John Gay, the playwright (to Jacks’s left), while William Hogarth sketches him on the right.

Jack Sheppard’s irons knocked off in the stone hall in Newgate.

Jack Sheppard  of Spitalfields (Mezzotint after the Newgate portrait by Sir James Thornhill, 1724) – “Yes sir, I am The Sheppard, and all the gaolers in the town are my flocks, and I cannot stir into the country but they are at my heels baaing after me…”

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13 Responses leave one →
  1. January 18, 2020

    To live for 22 years and have prominence for two months is much too short. He probably was intelligent and gifted. How very sad

  2. paul loften permalink
    January 18, 2020

    It seems that every so often in the pages of history either a man or woman is endowed with too many gifts for their own good. Jack had it all, good looks, charisma, amazing strength, intelligence, and a hand and brain that could solve the complexities that nobody else could. The result was envy from the rich and powerful who presumed that they alone should possess it all, even the roll of cloth and two silver spoons
    Not much has changed despite the passing of the years.
    Long live the spirit of Jack Sheppard !

  3. Amanda permalink
    January 18, 2020

    l agree with Mathilde.
    Saddened that his extraordinary skill was not recognised and harnessed rather than snuffed out.

  4. Charlotte permalink
    January 18, 2020

    I wonder what happened to Elizabeth Lyon.

  5. January 18, 2020

    Now, THAT was a lad with a death-wish.

  6. January 18, 2020

    What an Incredible Life. It was almost a book, Not a real life!! 💖💝❤💘💕💞🌹😢

  7. Amanda permalink
    January 19, 2020

    Today’s fascinating GA blog and Charlotte’s question above inspired me to spend Sunday afternoon seeking more answers to Jack’s devil- may-care existence and why he never went on the run after his pains to escape.

    The link gives Jack’s own alleged detailed blow by blow account of his final escape, after which he remained ‘on the doorstep’ in his old drinking haunts, ignoring his mother’s plea to flee the kingdom.

    He did not appear to want to get away or escape.
    He hid nearby at Tottenham Court for 3 nights until he’d shed his irons.
    He returned to his ‘local’ where he openly drank himself silly amongst his notorious pals and was easily apprehended for the final time.

    We read he’d had a very emotional infancy and childhood with the death of his father, sibling and a later guardian.
    And also his mother was at one time in Bedlam lunatic asylum.

    During his successful 5 year disciplined carpentry apprenticeship he was described as an “orderly boy” rather than wayward or of unsound mind.

    Meeting (Edgware) Edgeworth Bess aka lady of the night Elizabeth Lyon, he blamed as his turning point. She had introduced him to a lifestyle he had never before had knowledge of.

    Yet other reports claim during his work as a skilled carpenter, his ambition was to gain work in Mayfair houses in order to rob them. Hard to deduce whether he already had a fearless propensity for crime before he made his careless choice of debauched drinking establishments.

    Reports show little trace of the buxom Elizabeth Lyon following Jack’s execution, apart from not appearing overly grief stricken.
    Her character by these accounts was not charismatic, cited as evil, treacherous and sometimes beating Jack who was a handsome if not diminutive 5 ‘4″

    His execution spot at the Tyeburn tree is now Speaker’s Corner at Marble Arch.

    Thank you so much for this blog GA. lt has led me to an enormous cache of history l may have departed never knowing.

    All l can personally deduce is that Jack had absolutely no fear of death and that he just lived for the notoriety of his escapes and the buzz of constantly “nicking stuff.”

  8. Ian Findlay permalink
    January 20, 2020

    There’s a very entertaining book, The Fatal Tree by Jake Arnott with Jack and Bess as the principal characters. It uses the gangland language ‘flash’ with a glossary to assist, and gives an excellent atmospheric account of London (or Romeville in flash) in the 1720s.

  9. Jill Wilson permalink
    January 20, 2020

    Great stuff! My immediate reaction when I started reading this was that it would make a fantastic play or musical, but then I read that John Gay had had the same idea…

    Perhaps George Cruikshank’s drawings could be the storyboard for a thrilling adventure film or the latest offering from Netflix?

  10. Evelyn permalink
    January 21, 2020

    Hi Gentle Author, thank you for your continuing research and leadership! Did you know that Jack Sheppard is one of the heroes of ‘The Baroque Cycle,’ by American author Neal Stephenson. This work was published as three separate books because it was too much to publish it as a single book (like happened with Tolkien’s Lord of the Rings trilogy). In The Baroque Cycle, Jack’s name is Jack Shaftoe. The three books are: Quicksilver; The Confusion; The System of the World. Neal Stephenson is one of America’s greatest living authors, perhaps you already are one of his readers. The Baroque Cycle time frame spans from the English Civil War to 1714, and features Isaac Newton, Leibniz, Jack, and many other key individuals. Give it a try and you won’t be disappointed. It is a prequel to Neal’s novel ‘Cryptonomicon,’ which was written before The Baroque Cycle. Thanks again for all that you do, I respect, admire, and love you more than words can convey.

  11. Fiona Potter permalink
    November 29, 2020

    A fascinating, well-written and illustrated article.

    In 1969 a film was made of Jack’s story. See

    Jack’s corpse was initially buried in St.Martins in the fields but was later disinterred and re-buried in, I believe, Highgate Cemetary.

  12. Tom Old permalink
    January 31, 2021

    How callous and cruel that poor Jack Sheppard was Never granted a Royal Reprieve , Of Course Not, these sad executions were the entertainment of the day !!!,

  13. Helen James permalink
    March 30, 2022

    Does any know where he is buried?

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